Buckle up, babes. We are about to embark on a journey through 100 of the best romance movies ever made.* From 1934 to 2018, we think we’ve compiled the ultimate romance list. “But I’ve seen all the romance movies,” you might be saying. Let us assure you that we felt the same way… until we started going through this list. This list has teen romance movies. It has steamy love stories. It even has action romance, because it’s all fair in love and war.
Not convinced? Find yourself a comfortable spot on the couch and tell us you don’t believe in love by the time you’ve watched all of these movies.
*This list has not been updated to include all the new romantic movies coming in 2020.
1. It Happened One Night (1934)
Inspired by Samuel Hopkins Adams’ short story “Night Bus,” It Happened One Night was the first movie to win all five of the major Academy Awards. It follows Ellie Andrews (Claudette Colbert), a bratty socialite who has just eloped with King Westley (Jameson Thomas). Her father is furious when he discovers the marriage, because he’s convinced King is nothing more than a gold digger. He insists that the marriage be annulled at once.
When Ellie runs away to New York to follow her husband, she meets Peter Warne (Clark Gable), a newspaper reporter who offers her a deal. If she gives him an exclusive on her dramatic love affair, he will help her to find King. But Peter helps Ellie to find something different instead: true love.
2. Gone With the Wind (1939)
On the eve of the Civil War, Scarlett O’Hara (Vivien Leigh) is deeply in love with Ashley Wilkes (Leslie Howard) and devastated to learn that he’s about to marry his cousin Melanie (Olivia de Havilland). Scarlett professes her love for Ashley, but he shuts her down, and they are interrupted by the announcement that the war has officially begun.
In a spur of the moment decision, Scarlett marries Melanie’s brother Charles (Rand Brooks) right before he leaves for war. Widowed by Charles’ death in battle, Scarlett continues to harbor feelings for Ashley. After another marriage ended by a swift and untimely death, Scarlett marries Rhett Butler (Clark Gable), who has been lusting after her for years. When Ashley realizes he loves Scarlett, she’s forced to choose between the man she’s loved nearly her whole life and her husband.
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3. Casablanca (1942)
Rick’s Café Américain is a fancy nightclub and gambling den in Casablanca frequented by French and German officials as well as refugees struggling to make it to America. Rick Blaine (Humphrey Bogart) is the club’s American owner. He claims to be a neutral third party, but is revealed to have supported the Ethiopians against Italy and the Loyalists in the Spanish Civil War.
Rick is gruff and bitter, the result of a broken heart. The culprit? Ilsa Lund (Ingrid Bergman). When Ilsa walks into Rick’s with her husband, Victor Laszlo (Paul Henreid), Rick is shocked. He’s never gotten over Ilsa, and when she asks him to save her and Victor’s lives, Rick can’t possibly refuse. Even if you’ve already seen Casablanca, play it once more. For old times’ sake.
Related: The Best Old Romance Movies That Still Make Us Swoon
4. Roman Holiday (1953)
Ann (Audrey Hepburn) is a princess who is tired of all the duties of being a royal. On a trip to Rome, she decides to give her security the slip and venture out on her own. When she falls asleep on a bench, she’s found by Joe Bradley (Gregory Peck). Joe has no idea of her true identity and offers to let her spend the night at his apartment.
At work the next morning, Joe, a reporter, realizes who is in his home and proposes the idea of an exclusive interview to his editor. Ann declines his offer to show her around the city and strikes out on her own. Joe, determined to get the story, follows her and pretends to run into her on the Spanish Steps, withholding his career from Ann. After a day of adventures, Ann and Joe develop feelings for one another, but their real lives threaten to destroy their magical day.
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5. Sabrina (1954)
A film adaptation of the play Sabrina Fair, Sabrina is the story of Sabrina Fairchild (Audrey Hepburn). Sabrina’s father is the chauffeur for the wealthy Larrabee family, and she has been raised alongside the Larrabee boys. She’s been in love with David Larrabee (William Holden) for as long as she can remember, but David, an infamous womanizer, has never paid her any attention.
Sabrina spends two years at school in Paris and returns a changed woman. She is cultured and refined, and suddenly the focus of David’s affections. David’s older brother Linus (Humphrey Bogart) is concerned about the ramifications if David were to cheat on his wife with Sabrina. In a desperate attempt to prevent a relationship between his brother and Sabrina, Linus attempts to woo the young woman. He’s successful…perhaps too much, as he find himself falling for Sabrina as well.
6. The King and I (1956)
At its heart, The King and I is inspired by the true story of Anna Leonowens, the tutor for the children of King Mongkut of Siam, but the screenplay was derived indirectly. It was adapted from the musical The King and I, which was based on the novel Anna and the King of Siam, which was inspired by Leonowen’s memoirs.
As the film opens, Anna Leonowens (Deborah Kerr) and her son Louis are moving from Wales to Bangkok so that she can tutor fifteen of the king’s children. Anna grows attached to the children but often struggles with the stark differences between her morals and ideas and those of the king. Her challenges come to a head when King Mongkut (Yul Brynner) orders Anna to obey him and calls her his servant. A strong, well-educated woman, Anna isn’t going to tolerate that sort of treatment and stands up to the fierce leader. The king has never been challenged in this way, and Anna’s bravery and backbone may very well just change the fate of Siam forever.
7. An Affair to Remember (1957)
When Nickie Ferrante (Cary Grant) and Terry McKay (Deborah Kerr) meet aboard the SS Constitution, they’re both in relationships. But Nickie, a notorious playboy, and Terry, a budding musician, are inexplicably drawn to one another. They become good friends and Terry accompanies Nickie to visit his grandmother, where their feelings for one another grow even stronger.
They make a plan: In six months, they will meet on the top of the Empire State Building, but they will only do so if they’ve ended their relationships and taken a leap of faith to embark on a new career path. As she rushes to their rooftop meeting, Terry is in an accident and taken to the hospital. Nickie assumes that he’s been stood up and gives up on Terry. Will their love be enough to overcome Terry’s difficult recovery and Nickie’s broken heart?
8. Some Like It Hot (1959)
In 1929, Chicago is in the height of the Prohibition Era. Speakeasies are flourishing and the gangsters who own them are thriving. Joe (Tony Curtis) and Jerry (Jack Lemmon) are working the speakeasy owned by mobster Spats Colombo (George Raft) when it’s raided. It turns out the police were tipped off by a rival gang, and Joe and Jerry find themselves caught in the middle of a dangerous gang war.
Dressed as women, Joe and Jerry, now Josephine and Daphne, join a girl band on its way to Miami. They’re both enamored with Sugar Kane (Marilyn Monroe), the group’s lead singer and ukulele player. They grow close with Sugar and are frustrated that their cover as women prevents them from making a move. Joe assumes a new identity to woo Sugar while Jerry, as Daphne, accidentally captures the heart of a middle-aged millionaire.
9. The Apartment (1960)
Bud Baxter (Jack Lemmon) is a bored office worker stuck in corporate America. In an attempt to make something of himself, he allows his managers to use his apartment for their trysts with their mistresses. In exchange, they write him glowing reviews and suggest a promotion.
Bud is awarded the promotion but only on the condition that he extends the same courtesy to the director of personnel, Jeff Sheldrake (Fred MacMurray). He’s devastated when he learns that Jeff’s mistress is Fran Kubelik (Shirley MacLaine), who he has just asked on a date. Bud has a big decision to make: his job or his heart?
10. Breakfast at Tiffany’s (1961)
Holly Golightly (Audrey Hepburn) isn’t your average socialite. She’s quite eccentric and spends one day a week visiting mobster Sally Tomato at Sing Sing prison. He pays her to visit him, but she’s still looking for money in the form of a wealthy husband.
Paul Varjak (George Peppard) is her new neighbor who’s just moved in next door. Paul is the boyfriend of Tooley (Patricia Neal), a wealthy older woman who funds his attempts at becoming a writer. Holly and Paul become good friends…eventually developing feelings a bit stronger than those of your average friendship.
11. West Side Story (1961)
A modern adaptation of Romeo and Juliet, West Side Story is based on the Broadway musical of the same name. Maria (Natalie Wood) is a teenage girl living in Manhattan with her parents and her brother, Bernardo (George Chakiris). Bernardo is the leader of a Puerto Rican gang called the Sharks. Maria is engaged to Chino, the young Puerto Rican man her family has chosen for her to marry.
Maria has no interest in her fiance and falls for Tony (Richard Beymer), a member of the Sharks’ rival gang, the Jets. The Sharks and the Jets are sworn enemies, so they must keep their relationship a secret. Unfortunately, the young star-crossed lovers don’t fare much better than Romeo and Juliet in this beautiful yet tragic musical.
12. My Fair Lady (1964)
The musical adaptation of Pygmalion, My Fair Lady is a beloved classic. Professor Henry Higgins (Rex Harrison) is an expert in linguistics who holds the strong belief that one’s place in society is determined by his or her manner of speaking. To prove that he can teach anyone to speak as if he or she were part of the nobility, he agrees to tutor Eliza Doolittle (Audrey Hepburn).
Eliza’s Cockney accent is so strong that she’s unable to get the job she wants in a flower shop. Professor Higgins’ employs fairly harsh tactics in his attempts to teach Eliza to speak with a “proper” accent. He’s about to give up on her when everything suddenly clicks. Though he treats her poorly, Higgins finds himself falling for Eliza, and he must find a way to win her back when she announces her engagement to another man.
13. The Graduate (1967)
Benjamin Braddock (Dustin Hoffman) is a 21-year-old college graduate with no aim in life. He was a successful athlete and did well in school but left college with absolutely no plans. Benjamin has returned home to his parents’ home in California to find himself...but finds something very different.
Mrs. Robinson (Anne Bancroft) is a close friend of his parents who spontaneously seduces the young man nearly 30 years her junior. Mrs. Robinson and Benjamin begin casually seeing each other, but it’s not Mrs. Robinson that Benjamin is falling for. It’s her daughter Elaine (Katharine Ross).
14. Love Story (1970)
The movie that popularized “love means never having to say you’re sorry,” Love Story is a tragedy based on Erich Segal’s novel of the same name. Oliver Barrett IV (Ryan O’Neal) is a wealthy hockey player at Harvard. Jenny Cavilleri (Ali MacGraw) is a working-class student at Radcliffe College. Oliver and Jenny come from two very different worlds, but fall in love all the same.
Devastated that Jenny plans to study abroad in Paris and leave him behind, Oliver proposes. His parents threaten to cut him off if he marries Jenny, but Oliver is not phased. The young, newly-married couple struggles financially, but they’re just happy to have one another. But everything falls apart when Jenny is diagnosed with cancer. Sometimes true love simply isn’t enough.
15. The Way We Were (1973)
Katie Morosky (Barbra Streisand) is Jewish, a Marxist, and loves to speak her mind. Hubbell Gardiner (Robert Redford) is a WASP without a care in the world who has no political opinions and simply coasts through life. Somehow, Katie and Hubbell are attracted to one another, but they don’t act on their attraction, and after graduating from college fall out of touch.
They reunite a few years later. Hubbell has just returned from serving in the Navy during World War II and Katie is working at a radio station. Though they’re even more different than they were in college, the attraction is still there. This time, Hubbell and Katie aren’t going to ignore what’s clearly between them.
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16. Grease (1978)
Sandy Olsson (Olivia Newton-John) is a good girl. Danny Zuko (John Travolta) is a bad boy. But in the summer of 1958, their high school stereotypes go out the window and they spend a romantic summer together. When Sandy returns to Australia at the end of the summer, the young lovers are convinced they’ll never get to see each other again.
On the first day of school that fall, Sandy and Danny are in for a shock. The Olssons have just moved to Danny’s town, which neither Sandy nor Danny realized. Danny is thrilled to be reunited with his gang, the T-Birds, but Sandy is horrified to see how he acts around his friends. Will summer lovin’ be enough to bridge the gap between a good girl and a greaser?
17. On Golden Pond (1981)
Ethel (Katharine Hepburn) and Norman (Henry Fonda) Thayer have spent their summers on Golden Pond for decades, and this summer is no different. Norman is always grumpy, and beginning to lose his memory. Ethel is fairly easygoing and willing to do whatever makes her husband happy.
This summer, they have a visitor: their daughter, Chelsea (Jane Fonda). Chelsea is accompanied by her fiancé Bill (Dabney Coleman) and his thirteen-year-old-son Billy (Doug McKeon). Billy is left at the lake when his father and Chelsea go on vacation. Though he is bitter at first, Billy bonds with Norman and brings out a fun-loving and rarely-seen side of the elderly man.
18. An Officer and a Gentleman (1982)
Zack Mayo (Richard Gere), a new recruit for the Navy, is about to start Aviation Officer Candidate School (AOCS). He’s dreamed of being a Navy pilot ever since he was a child, and he’s determined as ever to make that dream a reality.
At a Navy Ball, Zack and his friend Sid (David Keith) meet Paula (Debra Winger) and Lynette (Lisa Blount). The Naval recruits have been warned that many of the local woman are looking for husbands at AOCS and will even fake pregnancies to secure a marriage proposal. Despite the warning, Zack falls for Paul and Sid falls for Lynette. They’re convinced the women are as genuine as they come, but one of their romances threatens to destroy everything the young men have worked for.
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19. Sixteen Candles (1984)
Sam Baker (Molly Ringwald) is devastated when she realizes that her whole family has been so consumed in planning her sister’s wedding that they’ve forgotten about her sixteenth birthday. Her day gets even worse when the magazine sex quiz she took falls into the hands of her crush, Jake Ryan (Michael Schoeffling).
Unfortunately for Sam, Jake is in a relationship and has never noticed her. The only person who has is Ted (Anthony Michael Hall), an awkward freshman who tries too hard to flirt with her. Sam’s convinced this birthday is doomed to be an utter disaster, but maybe she gave up hope too soon…
20. Splash (1984)
When he was eight years old, Allen Bauer couldn’t swim, but jumped into the ocean to get a better look at something he saw under the surface. It was a girl, and when he held her hands, he could breathe underwater. But when he’s pulled out of the water, the experience is chalked up to oxygen deprivation.
Twenty years later, Allen (Tom Hanks) returns to Cape Cod, where he had his traumatic childhood experience. He’s just broken up with his most recent girlfriend, is convinced he’s never going to find love, and has gone to the Cape to escape. When he falls into the ocean, he is once again saved by the mysterious and beautiful woman (Daryl Hannah). After bringing him to shore, she dives back into the water, turning into a mermaid. Allen is sure this is the last he’s seen of the beautiful woman, but she shows up in New York City, turning his life upside down.
21. Pretty In Pink (1986)
Andie Walsh (Molly Ringwald) and Duckie Dale (Jon Cryer) are high school seniors. They’ve been best friends for years. Duckie is secretly in love with Andie, but she sees him as nothing more than a friend.
Prom is coming up, and the friends are dateless. Duckie finally works up the nerve to ask Andie to go out with him, but she dismisses him, oblivious to his feelings. Her sights are set on Blane (Andrew McCarthy), a popular kid at school, but Andie realizes that it’s not very easy–or very fun–to date one of the cool kids.
22. Dirty Dancing (1987)
Baby (Jennifer Grey) and her family are spending the summer at Kellerman’s, a resort in the Catskills. Though her father forbids her from seeing him, Baby develops a crush on Johnny Castle (Patrick Swayze). Johnny is the older and much more, uh, experienced, dance instructor at Kellerman’s.
Johnny brings Baby into the world of the resort staff, where she sees all the dirty dancing they do at their parties. When his dance partner is dangerously in need of an abortion, Johnny is desperate to find a replacement. Baby volunteers to help fund the abortion and take part in the dance, and the pair spend the rest of the summer rehearsing–and falling madly in love.
23. Moonstruck (1987)
Loretta Castorini (Cher) is a thirty-seven-year-old widow who’s still living with her parents and grandfather. Miserable, she agrees to marry Johnny (Danny Aiello), even though she doesn’t truly love him. While her fiancé is in Italy with his dying mother, Loretta takes charge of planning the wedding.
With Johnny away, it falls on Loretta to invite his younger brother, Ronny (Nicolas Cage), to the festivities. The two brothers are estranged as the result of an accident for which Ronny blames Johnny. Still harboring a great deal of anger for his brother, Ronny feels no shame in making a move on Loretta. With Johnny an ocean away, Ronny and Loretta fall quickly and deeply in love. But Johnny won’t be gone forever, and his impending return forces everyone to face reality.
24. The Princess Bride (1987)
In this twist on a more traditional fairy tale, Buttercup (Robin Wright) falls in love with her farmhand Westley (Cary Elwes). But a poor farmhand cannot possibly marry this beautiful maiden. Wesley must go off and earn his own fortune before they can say “I do.”
As Westley sets off, his ship is attacked and he’s presumed dead. A heartbroken Buttercup eventually accepts a marriage proposal from Prince Humperdinck (Chris Sarandon). Before long, Buttercup discovers her fiancé is evil and tries to reunite with her one true love, who may or may not still be alive.
25. Crossing Delancey (1988)
The two sides of Delancey Street may as well be different worlds. At least that’s how it feels to Isabelle Grossman (Amy Irving). Isabelle is a young Jewish woman who works at a bookstore on the Upper West Side of Manhattan. She frequently visits her very traditional grandmother who lives on the Lower East Side, requiring her to quite literally cross Delancey.
Isabelle has a budding romance with author Anton Maes (Jeroen Krabbé) who introduces her to a world nothing like that of her grandmother’s. Meanwhile, Isabelle’s grandmother is concerned that her granddaughter is not yet married and with the help of the local matchmaker, introduces Isabelle to Sam Posner (Peter Riegert). Sam is the owner of a pickle shop on the Lower East Side and though she prefers the glamorous world of Anton, she finds herself inexplicably drawn to the working-class man.
26. Mystic Pizza (1988)
Kat (Annabeth Gish), Daisy (Julia Roberts), and Jojo (Lili Taylor) are waitresses at Mystic Pizza, a pizza joint in Mystic, Connecticut. Kat and Daisy are sisters. Kat is hardworking, brilliant, well-behaved and the “perfect daughter.” Daisy is rebellious, desperate to get out of Mystic, and looking for love. Daisy begins dating a wealthy white boy of whom their Portuguese mother is suspicious, while Kat develops feelings for the father of the child she babysits. Meanwhile, Jojo is madly in love with her boyfriend but can’t seem to make the relationship work. Mystic Pizza follows the three girls as they grow up and are forced to navigate friendship, relationships, and ambition.
Julia Roberts’ first critical success and Matt Damon’s film debut aren’t the only things that make Mystic Pizza special. The film went on to inspire the creation of a restaurant and frozen pizza company of the same name. Talk about good enough to eat.
27. Working Girl (1988)
Tess McGill (Melanie Griffith) is an intelligent and hardworking woman who wants nothing more than to become an executive on Wall Street, but the only things she has is very bad luck. After being tricked into going on a date with an offensive colleague, she loses her job in mergers and acquisitions and is demoted to be the assistant to financial executive Katharine Parker (Sigourney Weaver).
Tess resents her boss and hates her own life, so when Katharine is in an accident and sent to the hospital, Tess takes her place. She proposes a successful merger deal and has an affair with Jack Trainer (Harrison Ford), Katharine’s on-again-off-again boyfriend. Everything is going great for Tess until Katharine returns and discovers what she’s done. Tess isn’t going to get away with it if Katharine has any say in the matter.
28. Say Anything… (1989)
Lloyd Dobler (John Cusack) is a jock, but that doesn’t stop him from falling for Diane Court (Ione Skye), a brain with an overprotective father. They’re just graduating high school and their lives are on two very different tracks. Lloyd has no plans beyond his dream to be a professional kickboxer. Diane has a fellowship waiting for her in England.
In a prime example of opposites attracting, Diane and Lloyd fall in love, but as the summer passes, Diane’s father pushes her to end the relationship. Lloyd is lost without Diane and in a last-ditch effort to win her back her pulls one of film’s most iconic stunts. He arrives at her house at sunrise to play “In Your Eyes” under her window. Be still our beating hearts.
29. When Harry Met Sally… (1989)
Over the course of twelve years, Harry (Billy Crystal) and Sally (Meg Ryan) discover the answer to the question “Can men and women just be friends?” When they first meet the summer after college, Sally drives Harry from Chicago to New York City, and they fight like cats and dogs. Harry baits Sally repeatedly, tormenting her with sexist comments and harsh judgements.
After parting at their arrival in New York, Harry and Sally periodically run into one another. Eventually, they develop a close friendship and attempt to remain just that as relationships and sex get in the way. In the end, they find the answer to the all-encompassing question: No. Well, at least not for Harry and Sally.
30. Edward Scissorhands (1990)
Edward (Johnny Depp) is basically a friendly version of Frankenstein’s monster. He was built by a scientist who died before he could complete his masterpiece, and as a result, Edward isn’t exactly fully functioning. His struggles to have any semblance of a normal life are exacerbated by the scissors that serve as his hands.
He’s in luck when he meets Peg Boggs (Dianne Wiest), a saleswoman with a bleeding heart. She brings Edward home with her, and he becomes a part of the family. He discovers that his scissors for hands provide him with a host of incredible talents and becomes a sensation in the neighborhood. But as Edward falls for the Boggs’ daughter Kim (Winona Ryder), he discovers that a normal life is extremely dangerous when your hands are as sharp as knives.
31. Ghost (1990)
One night, Sam Wheat (Patrick Swayze) and his girlfriend, Molly Jensen (Demi Moore), are out for a walk near their apartment in Manhattan. Sam is shot by a mugger and suddenly finds himself looking at Molly holding his lifeless body. He struggles to come to terms with being a ghost and is infuriated that he can’t communicate with Molly.
Sam finds that he can communicate with Oda Mae Brown (Whoopi Goldberg) a phony psychic who is surprised by her talent to communicate with a ghost. Through Oda, Sam warns Molly that she’s in danger and that his death was an intentional murder, not the byproduct of a mugging. Molly is hesitant to believe Oda, but in the end, her love for Sam beats her skepticism.
32. Pretty Woman (1990)
Pretty Woman isn’t your average Cinderella story. Vivian (Julia Roberts) is a sex worker on Hollywood Boulevard when Edward Lewis (Richard Gere) pulls up asking for directions. Edward is a businessman from out of town who’s hopelessly lost and incapable of driving the stick shift car he’s driving. Vivian directs him back to the hotel and leaves to catch the bus back.
Edward intercepts her, hiring her for the night. Though it’s simply another of Edward’s business propositions, he begins to fall for Vivian and offers her $3,000 to pretend to be his girlfriend for the week. Vivian develops feelings as well, but is upset when their relationship doesn’t play out like a fairytale…or does it?
33. Groundhog Day (1993)
Phil Connors (Bill Murray), a Pittsburgh weather man, is furious when he’s assigned to cover the events of Groundhog Day in Punxsutawney. He very unenthusiastically records a segment and has every intention of returning to Pittsburgh that night, but he and his team are snowed in.
The next morning, and every day that follows, Phil wakes up only to find that it’s still Groundhog Day. The first few times he lives the loop he enjoys himself, but he quickly becomes severely depressed. Phil finds that nothing, not even his own death, can end the loop. Until one thing does: Love.
34. Sleepless in Seattle (1993)
When Maggie Baldwin dies of cancer, her husband Sam (Tom Hanks) and eight-year-old son Jonah (Ross Malinger) are overwhelmed by their grief. A year and a half later, Sam continues to mourn her death, and Jonah pushes his father to call into a talk show to open up about her. The story touches listeners around the country, including reporter Annie Reed (Meg Ryan).
Though Annie is engaged, she is drawn to Sam and, inspired by An Affair to Remember, writes a letter to him asking that he meet her at the top of the Empire State Building. Annie’s coworker secretly mails the letter, and Jonah is thrilled when he reads it. Though he is unable to convince Sam to meet the woman from the letter, Jonah writes back agreeing. It seems impossible that the meeting will happen, but nothing is impossible when it comes to true love–and romance films.
35. Four Weddings and a Funeral (1994)
Charles (Hugh Grant) is a terribly awkward British man who means well but often struggles to connect with others. At a wedding in Somerset, he meets Carrie (Andie MacDowell), an American woman. They spend a magical night together before parting ways, assuming they’ll never see each other again.
Much to their surprise, they run into one another four more times at three weddings and a funeral. Each time, it’s clear that there’s something between the Brit and the American, but they never seem to be on the same page.
36. Before Sunrise (1995)
Jesse (Ethan Hawke) and Celine (Julie Delpy) are both still reeling from their respective breakups. When they meet on the train to Vienna, they spontaneously get off together to explore the city. Exhilarated by the foreign city and their spontaneity, they share a passionate kiss.
They spend one long night together, exploring and discussing their deepest thoughts. It’s a night that has the potential to change their lives forever. But will they drop everything to be together, or return to the reality of their responsibilities?
37. Clueless (1995)
Cher (Alicia Silverstone) is spoiled, obsessed with fashion, and the most popular girl in school. She’s used to always getting her way, and if something doesn’t go her way, she knows exactly how to manipulate everyone and everything into doing what she wants. She’s improved her grades by setting up two teachers, and has transformed the new girl into the second-coolest girl in school.
The only person who seems impervious to her charms is her ex-stepbrother, Josh (Paul Rudd). He’s judgmental and disappointed by Cher’s lack of interest in anything beyond the superficial. But when Cher finds herself falling for him, she’ll do whatever it takes to make him believe she’s more than just a pretty face.
38. Sense and Sensibility (1995)
An adaptation of Jane Austen’s novel of the same name, Sense and Sensibility is a classic tale of love. Two sisters, Elinor (Emma Thompson) and Marianne (Kate Winslet) Dashwood are suddenly left with nothing when their father dies and their half-brother leaves them empty-handed.
Though the sisters are struggling to adjust to life as peasants, they still have time to pursue gentlemen callers. Marianne is smitten with both John Willoughby (Greg Wise) and Colonel Brandon (Alan Rickman). Elinor has fallen for Edward Ferrars (Hugh Grant), who’s wholly unavailable. Marianne and Elinor begin to wonder if they’re ever going to fulfill their dreams of settling down with loving husbands.
39. While You Were Sleeping (1995)
Lucy (Sandra Bullock) works for the Chicago Transit Authority and has been lusting after a particular commuter, Peter Callaghan (Peter Gallagher), for a while. They’ve never interacted, until Lucy rescues him from the path of an oncoming train. Misunderstanding the relationship–or lack thereof–between Lucy and Peter, a nurse leads Peter’s family to believe that Lucy is his fiancé.
Too overwhelmed to contradict the Callaghans, Lucy is welcomed as a member of the family. As they wait for Peter to wake up from a coma, Lucy develops feelings for his younger brother, Jack (Bill Pullman). When Peter wakes up and assumes he’s forgotten his fiancé due to amnesia, Lucy must choose between keeping up the charade and being with the man she truly loves.
40. Jerry Maguire (1996)
Jerry Maguire (Tom Cruise) is an uber-successful, albeit sleazy, sports agent. One day, he’s struck by a desire to change and writes a memo that gets him fired from his fabulous job. In an attempt to retain the athletes who are already his clients, Jerry teams up with Dorothy Boyd (Renee Zellweger) to start his own agency.
If you’re going to be successful, you’ve got to show them the money, which Jerry and Dorothy certainly do not have. What they do have is a budding romance. While struggling to keep their new business afloat, Jerry and Dorothy find themselves falling for one another.
41. Romeo and Juliet (1996)
We all know the story and the brutal ending, but it’s director Baz Luhrmann’s touch that makes this retelling so brilliant. Set in Verona Beach, the Capulets and the Montagues are warring mafia rivals. When Romeo (Leonardo DiCaprio) spots Juliet (Claire Danes) at a party, it’s love at first sight.
In a rapid-fire chain of bloody deaths and hurried teenage lust, Romeo and Juliet secretly marry. When Juliet’s family declares she must marry someone else, she foolishly turns to a fake suicide plot. The movie ends the same way we expect, but it’s the gorgeous imagery and beach scenes that change the way we watch this movie. From the pair’s first meeting while staring at each other between an aquarium to the gruesome double suicide, this movie is not your grandmother’s Shakespeare.
42. One Fine Day (1996)
After being late to the bus for her son Sammy’s (Alex D. Linz) field trip, Melanie (Michelle Pfeiffer), a single mother, is forced to work together with fellow single parent, Jack (George Clooney) to entertain their children throughout a busy work day. When the pair share a cab, they accidentally switch cell phones, paving the way for a series of mishaps.
As the day goes on, Melanie and Jack are thrust into comical situations with their children while they answer each other’s phones, help each other with work assignments, and figure out last-minute costumes for their respective children. As the day gets more hectic, feelings begin to arise between the couple. In this case, being a working single parent is no match for falling in love.
43. As Good As It Gets (1997)
Melvin (Jack Nicholson) is a novelist with obsessive-compulsive disorder. He tries not to interact with anyone but the server at his favorite diner, Carol (Helen Hunt), who’s the only person that can tolerate him. When Melvin’s neighbor, a gay artist named Simon (Greg Kinnear), is attacked in a robbery, Simon’s agent makes Melvin agree to take care of Simon’s dog while he recovers.
Melvin grows attached to the dog, and his life gets better in every way since he has someone to care for besides himself. The dog also helps him get more attention from Carol. Through a series of good deeds and a love for the dog, a friendship grows between Melvin, Carol, and Simon. While a dog is no real cure for OCD, love and friendship might help it seem more manageable. The story goes outside the bounds of your classic rom-com, and it even landed both Nicholson and Hunt Academy Awards.
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44. My Best Friend’s Wedding (1997)
Julianne (Julia Roberts) and Michael (Demot Mulroney) always agreed to get married at 28 if they were both single. But when 27-year-old Michael calls Julianne to tell her he’s marrying a 20-year-old named Kimmy (Cameron) in four days, Julianne realizes that she’s been in love with Michael all along. She heads to Chicago to stop the wedding and tell Michael how she feels.
As Julianne attempts to sabotage the wedding, she uses her gay friend George and pretends to be engaged to him to make Michael jealous. Basically, Julianne makes a bunch of foolish choices and in the process hurts many of the people closest to her. While it may seem predictable, the best part of this movie is the fact that things don’t turn out exactly how you’d think.
45. Titanic (1997)
Our hearts are still having a hard time moving on from this Leo and Kate classic. When divers in 1996 are looking for a rare diamond hidden in the remains of the Titanic, elderly Rose comes to help them find it, since she was the original owner. This brings back memories of the Titanic for Rose. In 1912, Rose (Kate Winslet) was 17 and just stepping onto the giant ship. At the same time, Jack Dawson (Leonardo Dicaprio) gambled his way onto the Titanic with dreams of being an artist.
Rose is deeply unhappy in her high-class life, and she is engaged to marry someone she doesn’t love. She considers jumping off the ship’s edge, but Jack steps in and tries to stop her. While at first Rose doesn’t want to be with Jack, she quickly falls in love with him and they start a secret affair. And then the Titanic never sinks, and they get to live happily ever after. Right? We wish. Even though we all know the ending, it’s still a beautiful story about following your own path and falling in love with the most unlikely of people. We’ll debate the door in the icy water later.
46. The Parent Trap (1998)
When Hallie Parker and Annie James (Lindsay Lohan and Lindsay Lohan) meet at summer camp, they immediately hate each other. The fact that they happen to look exactly the same doesn’t help, either. After a series of pranks, they’re forced into the “Isolation Cabin” together, where they realize they are twins who were separated at birth. The twins decide to switch places, one in California, the other in London, so they can meet the parent they’ve never known.
While Hallie has a blast with her unwitting mom Liz (Natasha Richardson) in London, Annie has trouble keeping her accent straight around her vineyard owner dad Nick (Dennis Quaid) and his new evil girlfriend. Hallie is found out, and is forced to return to California with her mom. When they arrive, the twins find out that Nick wants to marry his girlfriend. Can the girls make their parents fall back in love before the wedding and before the family is forced to be separated again?
47. Shakespeare in Love (1998)
We all like to imagine that Shakespeare’s own love life was as inspired as his plays. In this movie, a young William Shakespeare (Joseph Fiennes) is suffering from writer’s block. But when Viola (Gwyneth Paltrow), a wealthy merchant’s daughter, disguises herself as a man and auditions for his play, something changes. Shakespeare questions her audition, and she runs away. She gets the part, but the real fun begins when Shakespeare meets Viola as a woman. They dance together and something lights up in both of them.
Inspired by Viola, Shakespeare begins writing a little play called Romeo and Juliet. Maybe you’ve heard of it? Unfortunately for Will and Viola, the bounds that keep Romeo and Juliet apart ring a little too true for their real lives. Even though Shakespeare in Love is fictional, we can’t help but hope that a love like this actually inspired Shakespeare.
48. There’s Something About Mary (1998)
Ted (Ben Stiller) has been in love with Mary (Cameron Diaz) since high school. But after a botched prom date (imagine a zipper and a painful injury), Ted hasn’t talked to her in 11 years. Now, he wants to track her down. He hires creepy Pat (Matt Dillon), a private investigator, to find her. That’s what happened without the Internet! But when Pat finds Mary, she’s so great that he falls in love with her.
What’s a PI to do? He lies to Ted about how Mary has turned out so that Ted won’t want to meet her. Meanwhile, he tries his best to woo her, but it turns out that tricking people into loving you doesn’t always work out. Ted’s a romantic, and he doesn’t care if Mary hasn’t turned out like he thought she would, so he heads out to meet her. But can he make it through Pat and Mary’s other suitors to redo that night at prom?
49. The Wedding Singer (1998)
Adam Sandler with a mullet — it's better than you’d think! The year is 1985, and weddings are all around. Puffed sleeves, people! Sadly for Robbie (Adam Sandler), a wedding singer, he’s just been left at the altar. But when he meets Julia (Drew Barrymore), he feels more hopeful. She wants him to help her plan her upcoming wedding to Glenn Gulia (Matthew Glave).
Julia, soon to be Julia Gulia, and Robbie spend more time together as he gets over his breakup and ruined wedding while they plan Julia’s wedding. Soon the pair realizes that they might have deeper feelings for each other than they initially thought. Will Julia become Julia Gulia? Or will Robbie whip out a sweet song for her and save both of them? Only time will tell.
50. You’ve Got Mail (1998)
Independent bookstores for the win. Kathleen (Meg Ryan) runs a struggling bookstore, and she’s constantly competing with Fox Books, an evil chain store owned by Joe Fox (Tom Hanks). This was the beginning of email and the Internet, and Kathleen and Joe take full advantage. Without knowing each other’s identities the pair begins an online romance through email.
In real life, Joe and Kathleen continue to hate each other. Her store goes under due to Fox Books’ success, and Kathleen realizes that even though her store and dream have died, Fox Books might not be so bad. When the two of them meet in real life with their email identities, they have to reconcile the love and the hate that unites them. Hey, at least they’re both book people!
51. 10 Things I Hate About You (1999)
It’s the ideal 90s romantic comedy. Inspired by Shakespeare’s Taming of the Shrew, 10 Things I Hate About You follows sisters Kat (Julia Stiles) and Bianca (Larisa Oleynik), who couldn’t be more different. Kat is smart, serious, downright rude to many of her classmates, and couldn’t care less about the “no dating” rule her father has implemented, because she’s full of disdain for the boys at her school. Bianca is ditzy, popular, and desperately wants a date.
When nerdy new kid Cameron (Joseph Gordon-Levitt) develops a crush on Bianca, the two of them devise a plan to get a date for Kat, thus making it okay for Bianca to date. The pair pays bad boy Patrick (Heath Ledger) to take out fearsome Kat, but when the two of them develop real feelings for each other, will everything come crashing down? This movie, set in beautiful Seattle, also gives us the gift of Kat’s version of a Shakespeare sonnet, titled “10 Things I Hate About You.”
52. Notting Hill (1999)
We all know that quote: “I’m just a girl, standing in front of a boy, asking him to love her.” The thing is that American movie star Anna (Julia Roberts) is not just a girl, and Will (Hugh Grant) really is just a boy. A bookstore owner in London, to be exact. When the couple meets at Will’s bookstore, Anna proves to be more than what her movies suggest. Though the two connect deeply, it seems impossible for them to ever be together due to their vastly different lives.
But their paths keep crossing. Though they try to stay away from each other, there’s a magnetic field between them that keeps them coming back together. Great supporting characters make this movie even better, and it’s the encouragement from his friends that gives Will the final push to see Anna as something more than just a movie star. After all, don’t we all want to be seen for something more than our label?
53. Love and Basketball (2000)
When Quincy (Omar Epps) meets Monica (Sanaa Lathan), they’re just kids who love basketball more than life itself. The two incredible athletes squabble a bit, but they also share a first kiss and remain friends as they grow up. In high school, Monica and Quincy are each stars of their basketball teams, though Quincy has a more natural charm while Monica tends to get over-emotional on the court. At prom, Monica reveals her feelings to Quincy and they make love for the first time.
They go to the University of Southern California as a couple, but things get harder as Quincy gets attention as the best player on the basketball team while Monica has to fight to play and is disliked by her coach. We follow Monica and Quincy for many years as they break up, make up, and always play ball. In the end, we’re cheering for their relationship like it’s the final minute in a tied-up championship game.
54. Meet the Parents (2000)
When you marry someone, you also marry their family. Unfortunately for nurse Gaylord “Greg” Focker (Ben Stiller), this family includes his girlfriend Pam’s (Teri Polo) intense, cold father, Jack (Robert DeNiro). As Greg tries to figure out a way to propose to Pam at her family’s house in Long Island, Jack is trying to figure out how to get Greg out of the family.
Through a series of unfortunate mishaps (spilled familial ashes, anyone?), Greg finds out that Jack is actually a retired CIA operative. While Greg tries to hang on for Pam’s sake, Jack finally gets his way as Pam breaks up with him. But Greg thinks he can find his way back into Pam’s, and Jack’s, good graces.
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55. Amélie (2001)
Amélie (Audrey Tautou) likes to skip rocks, dip her hands into grain, and mourn the loss of her childhood fish. Let’s put it this way: She is very lonely. She works at a cafe in Montmartre, France, but it’s not fulfilling. When she finds a tin container in her bathroom full of childhood relics, she sets out on a mission to find the original owner. As she completes the well-meaning task, she takes it upon herself to improve every life she can.
She helps a blind man see the world around him, sets up couples, and befriends a fragile painter in her apartment building. All the while she is playing a game of cat and mouse with Nino (Mathieu Kassovitz), a similarly lonely man who’s missing his photo album of rejected photo booth pictures. The movie is whimsical and romantic at its heart, but the true joy is watching for small moments of joy and the pleasure of appreciating the banal instances in life.
56. Bridget Jones’s Diary (2001)
In this hilarious retelling of Jane Austen’s Pride and Prejudice, Bridget Jones (Renee Zellweger) navigates singlehood in her 30s. Through an endless diet of cigarettes, ice cream, and self-help books, Bridget finds her way into the bed of publishing magnate and certified sex god, Daniel Cleaver (Hugh Grant).
When Daniel cheats on her with a rude American, Bridget finds herself at a new rock bottom. All the while, Bridget’s old playmate from childhood keeps finding his way into her business. Mark Darcy (Colin Firth) is a grumpy, divorced barrister who seems to think he’s far above Bridget’s shenanigans. But when he confesses his feelings for her, will she put her pride aside in favor of sweet conversations and ugly Christmas sweaters?
57. Moulin Rouge! (2001)
In this musical set in Paris in 1900, romantic writer Christian (Ewan McGregor) falls (literally) into a writing job in the Bohemian movement. After writing Spectacular Spectacular for the Moulin Rouge, Christian meets Satine (Nicole Kidman), though she is under the pretense that he is the wealthy Duke.
The movie is wild, colorful, and yes, a musical. Although their love might be short-lived, Christian and Satine make the most of their time and we get to see Nicole Kidman as a courtesan. Big Little Lies, who?
58. A Walk to Remember (2002)
Nicholas Sparks, how does this still hurt 16 years later? In what seems like a classic bad-boy-meets-good-girl scenario, rebellious Landon (Shane West) has to participate in a school play as punishment for a prank. There, he meets the local minister’s daughter, Jamie (Mandy Moore). She’ll help him learn his lines, with one rule: don’t fall in love with her.
Does he fall in love with her? Absolutely. Oh, is that a spoiler? You totally knew that was coming. But what comes next isn’t your classic rom-com formula. All we’re saying is that The Fault in Our Stars had to get some inspiration somewhere. Good luck!
59. About a Boy (2002)
Rom-com king Hugh Grant strikes again as Will, a wealthy man in his thirties who can’t seem to move out of boyhood. As a ploy to meet women, he makes up an imaginary son and goes to single parent meetings. You know, as normal people do. There, he meets Marcus (Nicholas Hoult), an incredibly uncool 12-year-old.
Marcus attaches himself to Will, and the pair forms a strange friendship. After a failed blind date between Marcus’s suicidal mother (Toni Collette) and Will, Will meets Rachel (Rachel Weisz), a single mother who believes that Will is Marcus’s father. Though Will and Marcus are an odd pairing, they help each other in a way that no one else can.
60. My Big Fat Greek Wedding (2002)
Toula (Nia Vardalos) is the black sheep of the family. At the age of 30, she’s still painfully shy, awkward, and unmarried. In her traditional Greek family, she’s a total outlier. But when she decides to quit working at her parents’ Greek restaurant and take a job at her aunt’s travel agency, everything changes.
She meets and falls in love with Ian Miller (John Corbett), a cute guy who is definitely not Greek. When they get engaged, it’s a wild ride towards the altar with her overbearing parents, grandparents, aunts, uncles, second cousins, etc. Toula deserves love after being overshadowed for her whole life, but the really rewarding part of this movie is seeing her fall in love with herself.
61. How to Lose a Guy in 10 Days (2003)
Andie (Kate Hudson) is the “How To” girl at her magazine. When her editor assigns her an article about how to lose a guy in 10 days, Andie knows she can pull it off. She spots Ben (Matthew McConaughey) at a party, and she’s sure she can lose him. Little does she know, Ben is trying to pull off a challenge of his own. He makes a bet at work that he can make a girl fall in love with him… in 10 days.
As Ben and Andie torture and romance each other, it becomes clear that both of their challenges may not be as easy as they thought. Through hairless dogs, fake therapy, and a huge diamond, this couple proves that 10 days is just about long enough to make something more real than they could have imagined.
62. Love Actually (2003)
Love actually is… all around. And the more than 24 (!) characters in this movie prove it. In an intertwining tale set over the few weeks before Christmas in London, nine stories overlap to showcase many different kinds of love. Even though it’s technically a Christmas movie, we enjoy it throughout the year. It’s the best ensemble romantic Christmas comedy of all time, people!
Favorite stories within the movie include awkward new Prime Minister (Hugh Grant, of course) falling in love with his assistant Natalie (Martine McCutcheon), and Daniel (Liam Neeson) helping his step-son (Thomas Brodie-Sangster) make moves on a crush. There are also some pretty heartbreaking moments, but we won’t spoil the Christmas classic for you. Watch it if only for the most awkward meet-cute of all time (think porn shoot lighting test).
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63. 13 Going on 30 (2004)
It’s 1987. Scrunchies and blue eyeshadow are in, and 13-year-old Jenna (Jennifer Garner) is devastatingly uncool. She’s dying to be a part of the “Six Chicks,” a girl gang led by evil Tom-Tom (Judy Greer). She invites the cool kids over to her birthday party, and her best friend Matty (Mark Ruffalo) gives her a “Jenna Dreamhouse” sprinkled with magic wishing dust.
Unfortunately, Jenna’s party is ruined when she’s tricked into kissing Matty. Devastated and embarrassed, Jenna locks herself in her closet and wishes she was just thirty, flirty, and thriving. When she opens her eyes, she finds that she really is 30, and she’s living her dream life. After she freaks out, she takes advantage of her cool adult existence. But when she realizes that being Tom-Tom’s friend and missing out on friendship with the now-very-hot Matty isn’t so great, she just wishes she could be 13 again.
64. 50 First Dates (2004)
In an unconventional love story, playboy Henry (Adam Sandler) meets his dream girl, Lucy (Drew Barrymore). Their first date is amazing, and Henry can’t believe his luck. But the next day, she has no idea who he is. Yes, Lucy has short-term memory loss from a tragic pineapple car accident.
Henry is so into Lucy that he doesn’t give up wooing her. Every day he tries something new to win her love. Even though Lucy’s dad and brother have given up hope that she’ll ever be able to have a normal life, Henry believes in her. Can we have one last first watch of this movie, please?
65. A Cinderella Story (2004)
Cinderella, but make it with Chad Michael Murray in his prime. We’re in. Sam (Hilary Duff) is in her senior year of high school, and she should be living it up. Instead, she’s stuck working for her evil stepmother (Jennifer Coolidge) at a diner. When a cell phone mix-up occurs, Sam starts texting a mystery guy.
And of course, it’s the hottest guy in school, Austin Ames (Chad Michael Murray). They meet at a masquerade party, but Sam is too scared of rejection to tell him who she really is. We get it, Sam! In the age of harmless teen movies, this one is still fun to watch 14 years later.
66. Eternal Sunshine of the Spotless Mind (2004)
Imagine erasing a bad relationship from your mind. That’s just what quirky, disorganized Clementine (Kate Winslet) decides to do after her breakup with her boyfriend, Joel (Jim Carrey).
When Joel finds out that he’s been erased, he chooses to erase Clementine from his brain. But as Joel’s memories of Clementine disappear, he finds himself scrambling to keep them. The pain of this movie is the heartbreak of seeing a relationship change and darken, but that’s also the joy. Clementine and Joel couldn’t be more different, but it’s up to them to decide if the hurt from love is worth the happiness it brings them at the end of the night.
67. The Notebook (2004)
Prepare your tissues. No matter how many times we watch this movie, we still end up in tears. An elderly man in a nursing home tells the story of Allie (Rachel McAdams) and Noah (Ryan Gosling), two lovestruck teenagers from opposite sides of the tracks. While Allie is expected to marry rich, Noah wants a simple life in a house he plans to restore. When their summer romance is thwarted by Allie’s parents, the two are forced to part, but Noah promises to write Allie every day.
But Allie never gets those letters. Behind both of their backs, Allie’s mother is hiding Noah’s love for her, leaving them both heartbroken. Allie tries to move on with someone her parents approve of, and she finds herself engaged. Noah can’t bring himself to let her go. When he and Allie are reunited years later, they find that they’ve changed, but their feelings for each other have not.
68. Brokeback Mountain (2005)
Jack (Jake Gyllenhaal) and Ennis (Heath Ledger) are hired to herd sheep for a summer in rural Wyoming. After nights of tension and sad baked beans, the men sleep together and develop a meaningful, romantic connection. But it’s 1963. In Wyoming. Both men leave that summer and marry women, though their feelings for each other do not disappear.
Throughout the years, Jack and Ennis meet sporadically at Brokeback Mountain, with Jack growing more and more impatient to stop living a lie, but Ennis fears what would happen if they were to live freely. After an explosive argument, Jack and Ennis part for good. The story is about love, but it’s the struggle to accept yourself despite all odds that makes this movie so heartbreaking. Watch with waterproof mascara!
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69. Hitch (2005)
Hitch (Will Smith), a dating coach, has helped countless men to win over the loves of their lives, but he’s never experienced love for himself. He’s simply a smooth operator who uses his industry tricks on any woman he finds attractive.
While helping his awkward client Albert (Kevin James) ask out socialite Allegra Cole (Amber Valletta), he meets Sara (Eva Mendes) a gorgeous tabloid reporter who’s looking for a story on Allegra. Sara seems impervious to his tricks, but her resistance just makes him all much more determined to win her over. Just remember: “Life is not the amount of breaths you take, it’s the moments that take your breath away.”
70. Pride and Prejudice (2005)
We can debate all day over which Pride and Prejudice movie is the best, but something has to be said for the 2005 Keira Knightley version. Born into a money-challenged family of five daughters, Elizabeth Bennet (Keira Knightley) has different aspirations than her silly and money-hungry mother. When Mr. Bingley (Simon Woods) moves into the estate down the way and romances Elizabeth’s sister Jane (Rosamund Pike), everything changes for the Bennett family.
With Bingley comes his snobby friend Mr. Darcy (Matthew MacFadyen), a wealthy man with something against the Bennett family. Elizabeth is turned off by his attitude, but they find themselves drawn to each other as Bingley and Jane fall in love. Elizabeth and Darcy are both stubborn, smart, and prideful. Can they move past their prejudice to create the perfect match? There’s not much physical touch in this movie, but the looks shared between Elizabeth and Darcy are enough to warm us through the winter.
71. Knocked Up (2007)
In a situation similar to your recurring nightmares, journalist Alison (Katherine Heigl) gets pregnant after an unfortunate one-night stand with stoner Ben (Seth Rogen). Alison decides not to have an abortion, and after Ben’s initial freakout, he tells Alison that he wants to be in the baby’s life.
In an effort to make a better life for their baby, incompatible Ben and Alison attempt a relationship. They learn what not to do from Alison’s sister, Debbie (Leslie Mann) and her husband Pete (Paul Rudd). Will Ben and Alison be able to make things work? Or will Ben stay rooted in his irresponsible ways? The great thing about Knocked Up is that we’re never really sure.
72. Atonement (2007)
It’s a story of jealousy, desire, and not knowing how to say you’re sorry for something irreplaceable. Lovers Cecelia (Keira Knightley) and Robbie (James McAvoy) are of a very different social class. When Cecilia's younger sister, Briony (Saoirse Ronan) sees them together, she’s both jealous and confused.
Briony constructs a lie that will change the lives of all three characters forever. Robbie ends up imprisoned, and Cecilia can never forgive her sister for the pain she has caused. As Briony gets older and spends her life taking care of fallen World War II soldiers, she attempts to atone for the lives she has ruined. Doesn’t sound very romantic? Think again. The love shared between Cecilia and Robbie is enough to keep us going through this heartbreaker of a drama.
73. P.S. I Love You (2007)
Get ready to ugly cry! In the Marley and Me of romantic comedies, we meet Holly (Hilary Swank) and Gerry (Gerard Butler). Gerry has just died from an illness, leaving Holly to pick up the pieces without the love of her life. But Gerry knew that Holly might need some help moving on, so he planned something amazing for her after his death.
In a series of letters received after she turns 30, Holly gets to reconnect with Gerry posthumously. No, not a ghost. But through these letters and with help from Holly’s friends and family, Gerry pushes Holly to continue living without him. Enjoy the Irish scenery and pints throughout her journey.
P.S. We’ll meet you on the couch with ice cream and tissues.
74. Juno (2007)
At sixteen, Juno MacGuff (Ellen Page) becomes pregnant by her friend Paulie Bleeker (Michael Cera). She’s smart, quirky, and a little weird. She knows she’s not ready to be a mom, so she heads off to get an abortion. The thing is, she can’t do it. She turns to adoption, and finds a perfect couple in the pennysaver ads in the newspaper.
The couple, failed rock star (Jason Bateman) and uptight Vanessa (Jennifer Garner) may seem great at first, but their shiny facade begins to crumble, ruining Juno’s hopes for her future baby. Meanwhile, Paulie just wants to be in Juno’s life if she’ll let him. It’s been over ten years since this movie came out, but a quote from Juno’s dad (J.K. Simmons) still sticks with us: “Good mood, bad mood, ugly, pretty, handsome, what have you, the right person will still think the sun shines out your ass. That's the kind of person that's worth sticking with.”
75. 27 Dresses (2008)
Not only has Jane (Katherine Heigl) been a bridesmaid 27 times, she’s now also dealing with the fact that her younger sister Tess (Malin Akerman) is marrying Jane's boss and secret crush, George (Edward Burns). Of course, Jane will be planning the wedding.
Jane meets Kevin (James Marsden), a reporter who writes wedding announcements. He’s cynical about the idea of marriage, and he decides to use Jane’s story as a jumping-off point for his investigative journalism career. Because what could make someone fall for you like exposing them publicly? Kevin realizes that maybe Jane and marriage aren’t so pathetic after all, but when his story runs in the paper, it could be too late.
76. The Curious Case of Benjamin Button (2008)
We forget that this movie is actually a romance because of the whole aging backwards thing. Curious, indeed! Benjamin Button (Brad Pitt) is born as an old man and begins to age in reverse. However, Benjamin is still just a kid trapped in a creaky body, so when he meets Daisy (Cate Blanchett) and she treats him kindly, he remembers her for the rest of his unusual life.
They stay in touch throughout the years, and she becomes a dancer. While the movie is centered around Benjamin’s odd life and the strange happenings around it, the movie always circles back to his relationship with Daisy. As Daisy grows older and Benjamin gets younger every day, the pair loves each other totally uniquely and beautifully. In a curious way, Benjamin’s age reversal makes his life even more meaningful.
77. Mamma Mia! (2008)
Cheesy? Check. ABBA tunes? Check. Meryl Streep and Colin Firth singing? Check. When Sophie (Amanda Seyfried) gets engaged, she really wants her dad to walk her dad down the aisle. The thing is, she doesn’t know who he is. When Sophie’s mom Donna (Meryl Streep) was her age, she had three separate love affairs and was later gifted with Sophie. So what’s a bride to do? She secretly invites all three prospective fathers to her wedding in Greece.
Through ABBA’s greatest hits, we meet Harry (Colin Firth), Sam (Pierce Brosnan), and Bill (Stellan Skarsgard). All three men have fond memories of Donna, but she is shocked to see all of them in one place. Sophie comes to love each one of the men that her mother fell in love with years before, and she realizes that the best parent she could ask for already exists: Donna. See you in Greece, Dancing Queens.
78. Nights in Rodanthe (2008)
In this Nicholas Sparks drama, Adrienne (Diane Lane) attempts to find herself and get over her cheating husband at a bed-and-breakfast in Rodanthe, North Carolina. It’s there that she meets Paul (Richard Gere), a surgeon with his own emotional problems. A storm approaches, and Adrienne and Richard talk to each other about their issues as they protect the inn and grow to like each other.
A romance is born out of the storm, and Paul decides to visit his estranged son (James Franco) in South America. The couple separates with the intention of reuniting when Paul returns from seeing his son. Through handwritten letters, they express their love for each other and they realize how changed they are due to meeting each other. But when they are meant to reunite, something unexpected comes between them.
79. (500) Days of Summer (2009)
Is love at first sight a real thing? Romantic architect-turned-greeting-card-writer Tom (Joseph Gordon-Levitt) seems to think so when he meets independent, carefree office assistant, Summer (Zooey Deschanel).
Despite Summer’s warning that she doesn’t believe in love, Tom falls for her. The anti-love story is told out of order, which gives us time to view the ways that Tom and Summer’s relationship is so perfectly doomed from the start. Set in beautiful Los Angeles over a period of (obviously) 500 days, Summer and Tom fight with each other and with their own preconceived notions of love.
80. The Time Traveler’s Wife (2009)
Long distance is hard for any couple, but Henry (Eric Bana) and Claire (Rachel McAdams) have very time-sensitive issues — time travel, that is! Claire grows up with sporadic visits from Henry, a man that will someday be her husband. But Claire meets Henry at varying stages of his life, and he even disappears at their wedding.
Because Henry has very little control over the way he time travels, it can be hard for the couple to connect. As they try to live a normal life, Henry and Claire struggle to have a baby, and then have to work to even be in the same place at the same time. Talk about a couple out of sync, but the love they have for each other can cross even the passage of time.
81. Up in the Air (2009)
Ryan Bingham (George Clooney) fires people. He’s a corporate downsizer, and his job requires him to travel around the country to fire workers. The thing is, he likes it. He loves the fact that he has almost 10 million frequent-flier miles, and he loves his casual airport flings with Alex (Vera Farmiga), another frequent-flier. So when Natalie (Anna Kendrick), a new hire, wants to change the way Ryan does his job, he’s not happy.
Natalie thinks that video firings are the future, and this would limit Ryan’s airborne lifestyle. To prove to her that his way is correct, Ryan takes Natalie in the air with him. Though it’s his career that hangs in the balance, it’s his personal life that might have to change. As his feelings grow stronger for Alex, he’ll have to reexamine what’s really important.
82. The Last Song (2010)
In the movie that brought us Liley (Myam? Cyrus-Worth?), Miley Cyrus plays a troubled teenager to Liam Hemsworth’s small-town boy. Ronnie is forced to move from New York to a beach town in Georgia with her father (Greg Kinnear) for the summer. She’s angry at him for leaving their family, and is reasonably upset to be stranded in Georgia. Ronnie is musically talented like her father, but she’s refusing to go to Julliard even though they’ve been courting her for years.
In walks Will, small-town football player and total goody two-shoes. He even volunteers with sea turtles. While at first Ronnie doesn’t want anything to do with him, he soon charms her into falling for him. Throughout the summer, Ronnie also warms up to her dad, who might be more similar to her than she thought. Of course, it’s Nicholas Sparks, so look out for that final twist of the sadness knife.
83. Leap Year (2010)
Anna (Amy Adams) is organized. She has her life planned to the final detail, except for one thing: she’s not married! The horror. Her boyfriend of four years (Adam Scott) has no plans to propose, so she takes it into her own hands. While he’s on a business trip in Ireland, she’ll take advantage of the Celtic tradition and propose to him on Leap Day. But things don’t really go according to plan.
Things begin to unravel when she misses her flight and has to stay in a small town called Dingle. There, she meets dreamy but grouchy Declan (Matthew Goode). He offers to take her to Dublin for 500 euros. Driving for several days across the Irish countryside with a cute guy? Yeah, you try not falling in love.
Related: Irish Romance Movies to Watch for St. Patrick's Day
84. Remember Me (2010)
Since his brother died by suicide, Tyler (Robert Pattinson) has had difficulty connecting with his father (Pierce Brosnan) and with the rest of the world. The only person he really cares about is his younger sister Caroline (Ruby Jerins). That is, until he meets Ally (Emilie de Ravin).
But Ally has family problems of her own, included a botched robbery that killed her mother on the subway tracks. The troubled couple bonds over struggle, and they begin to let themselves feel things they’d been blocking off for years. As they finally embrace joy, a tragedy could ruin everything. Caution: the ending of this movie is quite controversial.
85. Crazy, Stupid, Love (2011)
When we meet Cal (Steve Carell), his perfect life with a beautiful wife, house, and children is crashing down. His wife Emily (Julianne Moore) is leaving him for another man. And that’s all Cal can talk about for the next few months as he sits at a bar and discusses it loudly with no one. Womanizer Jacob takes notice at the bar, and can’t handle the complaining any longer. As he takes Cal under his fashionable and smooth wing, both of their lives change.
Cal gets a new wardrobe and shuts up about Emily long enough to sleep with other women and make some much needed changes in his stagnant life. Meanwhile, Jacob (Ryan Gosling) is falling for Hannah (Emma Stone), a girl who might take him out of the dating game forever. When Cal and Jacob’s lives tangle in an unexpected way, they’ll wish there were things they could unlearn about each other. If anything, watch for the Ryan Gosling abs and Dirty Dancing lift.
86. Les Misérables (2012)
If only he didn’t steal the bread! In this French revolution musical epic, Jean Valjean (Hugh Jackman) leaves prison after a 19 year sentence. Immediately he breaks his parole and steals money to reinvent himself as a factory owner and mayor. His parole officer, Javert, vows to find him and arrest him again.
In Jean Valjean’s factory there is a young worker, Fantine (Anne Hathaway), struggling to take care of her daughter. Thrown out on the streets, she is forced to prostitute herself and even sell her hair. When she dies, Jean Valjean finds himself taking care of her daughter, Cosette (Amanda Seyfried), who blossoms into a beautiful young girl in love. Is this a love story? It’s a lot of things, but we’re definitely in love with Fantine’s dream of time gone by.
87. The Vow (2012)
The movie begins with a tragic accident as Paige (Rachel McAdams) and Leo’s (Channing Tatum) lives are changed forever when a car hits them. Paige doesn’t remember who she is, or who Leo is. She also can’t understand why her relationship with her parents is strained, and she still has feelings for her former fiance (Scott Speedman).
As Paige struggles to acclimate to her new/old life, Leo does everything he can to remind her of why she fell in love with him. The movie is heartbreaking because we understand both sides of the couple’s struggle. Paige has awoken to find a life with which she is completely unfamiliar, and Leo has lost his wife. However, a vow is a vow, and Leo fights to show her who she used to be.
88. Silver Linings Playbook (2012)
Pat (Bradley Cooper) has just been released from a mental institution to the care of his football-obsessed parents (Robert De Niro and Jacki Weaver). He’s lost his job, his wife, and his sanity, but he’s determined to get it all back. Then, he meets Tiffany (Jennifer Lawrence), a widow with her own emotional problems. She is instantly attracted to Pat, but he turns her down because of his devotion to his ex-wife.
Tiffany isn’t one to give up, and she tells Pat that she’ll deliver a letter to his ex-wife if he participates in a dance competition with her. Pat agrees out of desperation, and the pair begins rigorous dance practice together. As Pat and Tiffany dance and spend more time together, Pat resists his budding feelings for Tiffany, but he may not be able to resist her quirky charm.
89. Moonrise Kingdom (2012)
It’s 1965 and 12-year-old orphan Sam (Jared Gilman) is at a summer camp for Scouts in New England. Suzy Bishop (Kara Hayward) is an equally precocious 12-year-old living in the same town. The two met in the summer of 1964 and have been sending each other letters ever since. It’s the letters that have led them to decide to run away together; neither of them are happy at home, and they believe they have fallen in love with each other.
They meet up and embark on a journey through mountains, water, and the wilderness in hopes to reach a cove on the island where they can be themselves. The rest of the scouts at camp, along with Suzy’s parents (Bill Murray and Frances McDormand), set out to find the pair and break up the couple. It’s young love, but Suzy, Sam, and Wes Anderson prove that children can be emotional, and certainly lonely for someone to connect with.
90. About Time (2013)
When Tim (Domhnall Gleeson) turns 21, his father (Bill Nighy) tells him an old family secret: the men in their family can time travel, and this includes Tim. Like many 21-year-old men, Tim’s really only worried about one thing, so he decides to use his newfound powers to get a girlfriend. His first attempt is a failure, so he takes a break until he meets Mary (Rachel McAdams), a young woman working in publishing. After time traveling and losing her phone number in the process, he works hard to make things right between them.
As Tim and Mary begin their lives together through love, marriage, children, and all the difficulties that accompany those rites of passage, Tim struggles to balance his wish to make every day perfect with real-life compromises. The movie begs the question: Can we come to appreciate a normal day?
91. The Spectacular Now (2013)
“I am serious… about not being serious,” says Sutter Keely (Miles Teller) as he gears up to maybe, maybe-not graduate from high school. Sutter is devastated after a recent breakup with his girlfriend due to his lack of motivation, but he still can’t get his act together. Maybe, he thinks, he just doesn’t care.
But something changes when he wakes up after a night of drinking on Aimee Finicky’s (Shailene Woodley) lawn. Aimee is hard-working and serious, and she rarely does anything for herself. The two spark up an unlikely friendship, and then romance, built over shared drinks out of a flask and trauma inflicted by their absent parents. As Aimee falls in love, Sutter scrambles to find meaning past the now. When a terrible accident occurs, the pair must deal with living life for the day, but also for tomorrow.
92. Pacific Rim (2013)
Sure, it’s not a traditional romance movie. And yes, maybe the lovers of this movie never even kiss. But the romantic vibes are off the charts. In a fictionalized version of 2013, a portal opens in the Pacific Ocean, giving way for huge monsters, the Kaiju, to escape from the underworld. People are recruited to pilot Jaegers, which are gigantic robotic machines. Two pilots control their Jaeger, and they’re linked together mentally, so the machine isn’t too emotionally stressful.
Raleigh (Charlie Hunnam) has been retired from the Jaeger game since his brother (Diego Klattenhoff) was killed by a Kaiju. But years later, he’s called back to help save the world. This time, his co-pilot is a young woman named Mako (Rinko Kikuchi). She has a dark past, and they’re an unlikely pair. But when you can show each other your thoughts, as you must as a pilot in a Jaeger, it’s impossible not to become close. With jaw-dropping scenes directed by Guillermo Del Toro, this is not your typical action movie. And though this pair may be more platonically connected than anything, you’ll still hear us chanting “Kiss! Kiss! Kiss!” every time they’re on screen together.
93. The Fault in Our Stars (2014)
Try not to cry too much, okay? Okay. Hazel Grace (Shailene Woodley) has terminal cancer, and it’s hard not to think about it all the time. But she’s still funny, smart, and appreciative of the world around her. When her mom makes her go to a cancer support group, she meets charismatic Augustus Waters (Ansel Elgort), a teenage boy who lost his leg to cancer, but is now cancer-free. The two of them bond, and they’re each happy to meet someone who sees them as more than their disease.
Hazel Grace shows Augustus her favorite book, but he’s annoyed about the abrupt ending. He tracks down the author’s assistant in Amsterdam, and the author invites the two of them to visit him. As the two of them plan their trip, they fall in love despite Hazel Grace’s declining health. In Amsterdam, Augustus reveals that his cancer has returned. The rest of the story is as heartbreaking as you can imagine, but in their short time together, Hazel Grace and Augustus discover that love can survive even the harshest of problems.
94. La La Land (2016)
This movie is as much a love story between two people as it is a tribute to the great city of Los Angeles. Mia (Emma Stone), an aspiring actress, and Sebastian (Ryan Gosling), a jazz musician, are struggling to reach their dreams in the city of angels. The two connect at a party, and it’s through their eyes that we see them fall in love with each other and with their own passions. The pair is often magic together, but they’re at their best when they’re encouraging the other to follow their dreams. You may find yourself rooting for their success as much as for their love story.
The story is about love, but it’s also about the lengths we’ll go to pursue our dreams and the people we may have to leave behind. For those of us that are romantics, the end can seem a bit bittersweet, but Sebastian and Mia finally learn to live – and love – in Los Angeles.
95. Beauty and the Beast (2017)
In a tale as old as time: A cruel prince is sentenced to a life as a beast. As he hides away in a forbidden castle, he waits for his curse to be broken by learning to love and be loved. Meanwhile, in the village below, book-loving free-spirit Belle (Emma Watson) avoids misogynistic men and longs for adventures like the ones in her stories. When her father goes missing, she finds that he’s been taken captive in the Beast’s castle. Belle begs the Beast to take her instead, and he agrees.
As Belle learns to accept her new life as a captive, she realizes that the castle may be more magical than it seems. When she makes friends with inanimate objects, she begins to see that the Beast may be more human than she initially thought. Belle and the Beast become closer, and when her father is taken to an insane asylum, he releases her with hopes that she will return to him. As the Beast is discovered and a witch hunt ensues, will Belle be able to save him? And can we argue that this story is really just about Stockholm Syndrome?
96. Call Me By Your Name (2017)
The year is 1983 and 17-year-old Elio (Timothee Chalamet) is wasting his summer away eating peaches by the pool in Northern Italy at his parents’ villa. That is, until his father invites 24-year-old PhD student Oliver (Armie Hammer) to live with them for six weeks. Elio and Oliver find themselves attracted to each other despite their age gap and contrasting personalities.
Through secretive courtship, Elio and Oliver grow closer throughout the summer until they share a climactic kiss, but Oliver warns that they should not stop “being good.” However, the growing attraction between the men continues to develop and eventually it can’t be ignored any longer. As the summer reaches its end, and Oliver’s departure nears, Elio deals with the beauty and heartbreak of his first love.
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97. The Shape of Water (2017)
This unique film took home the Oscar for best picture at the Academy Awards in 2018. Told mostly through the perspective of mute custodian Elisa (Sally Hawkins), a love story unfolds in the most peculiar of ways. When Elisa’s place of work, a secretive government laboratory, captures a human-like amphibian, Elisa finds herself drawn to the creature. While everyone else underestimates Elisa due to her lack of speech, she and the creature are able to share a bond beyond words.
When Elisa gets word that the creature is to be destroyed and studied, she takes it into her own hands. So where’s the love story? The connection between Elisa and the creature turns out to be much more than friendly. As the creature struggles to survive out of water, Elisa may realize that she never belonged above sea level, either.
98. Love, Simon (2018)
Simon (Nick Robinson) is just like any other teenager. He has great friends, supportive parents (Josh Duhamel and Jennifer Garner), and a huge secret — He’s gay. When another boy posts on his high school’s anonymous sharing page that he has the same secret, Simon jumps at the chance to finally share what he’s been hiding. Simon and “Blue,” the other boy, become fast pen pals… and maybe something more.
The budding romance is quickly thwarted when a classmate (Logan Miller) finds Simon’s emails and blackmails him. Though Simon courageously tries to balance blackmail, his friends, and finding out the identity of Blue, it proves to be too much for him to handle. As it all comes crashing down, Simon has to choose to accept himself and hope that the people around him will do the same. I won’t give away the identity of Blue, but know that it had me questioning the answer right up until that last, sweet moment.
99. Crazy Rich Asians (2018)
There’s rich, and then there’s crazy rich. NYU economics professor Rachel (Constance Wu) discovers that her boyfriend Nick’s (Henry Golding) family falls into the latter category when the couple visits Singapore for a wedding. Nick tells Rachel that his family is “comfortable,” but when they arrive, Rachel realizes that his family are basically the Kardashians of Singapore.
Rachel also has the realization that Nick’s mother Eleanor (Michelle Yeoh) absolutely hates her. As Rachel tries to understand Nick’s world, she comes to know things about herself, her family, and the strength of her relationship with Nick. Through trials of love, wealth, and insane parties, will Rachel end up with the love of her life, or will Eleanor stand in the way?
100. To All the Boys I’ve Loved Before (2018)
We know you've already watched it three times, but this movie is a classic in the making. Lara Jean Covey (Lana Condor) spends much of her time writing love letters she'll never send. Her current object of affection is her older sister's ex-boyfriend, Josh (Israel Broussard). When her little sister Kitty (Anna Cathcart) sends out the letters, Lara is forced to deal with the repercussions of her own romantic thoughts.
Luckily for the viewer, this means that she has to confront all of her old crushes, including Peter Kavinsky (Noah Centineo), a popular but kind guy she kissed years ago. To avoid talking to Josh about her letter, Lara Jean and Peter come up with a plan to pretend to date until everything blows over. There's nothing we love more than a "let's-pretend-we're-dating-as-we-actually-fall-in-love" plot, and this movie delivers with a depth and wholesomeness that we've been craving.
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Featured still from "When Harry Met Sally" via MGM