It’s almost impossible to pick a top decade for romantic comedies, but the 2000s certainly contained a lot of favorites. It was a heyday for actors like Matthew McConaughey, Hugh Grant and Katherine Heigl, and also a period when rom-coms started to become a little more unexpected (see: Legally Blonde).
From Love Actually, the Christmas romance that sparked a whole new subgenre of holiday romance movies, to indie hit 500 Days of Summer, which made the world fall in love with Joseph Gordon-Levitt (again), these are our top 10 2000s romantic comedies.
Love & Basketball (2000)
This sports rom-com starring Sanaa Lathan and Omar Epps, as Monica and Quincy, two budding sports stars who grew up together in Los Angeles. There’s always been a spark between them, and the two date throughout college, but break up when they both choose their love of the game over one another Years later, can they make it work—or will basketball always be their true love?
Legally Blonde (2001)
Featuring Reese Witherspoon in her peppiest role to date as Elle Woods, Legally Blonde is the story of a girl doing whatever it takes to get her happily ever after, including getting into Harvard Law School. (What, like it’s hard?) But soon enough, Elle realizes the man she was chasing is not what she really needs.
Bridget Jones's Diary (2001)
Love Actually (2003)
While Love Actually certainly has its comedic moments, this movie is so loved by romance fans because of its ability to hit all the emotions. Featuring an ensemble cast of, well, almost every big British celebrity from the early aughts, this film is the reason we have entirely unreasonable expectations of having a wedding with a surprise pop-up orchestra.
Something's Gotta Give (2003)
Eschewing the idea that romantic comedies only star actors under 40, this tale of later-in-life love stars Jack Nicholson as a womanizer dating a much younger woman, Marin. But when he meets Erica, (Diane Keaton) Marin’s mother, he realizes what he’s been missing out on.
13 Going on 30 (2004)
Featuring Big-like magic, this iconic movie shows a tween girl jumping 17 years forward in her life, without any memory of growing up. Now that Jenna (Jennifer Garner) is essentially living as a 13-year-old in a 30-year-old’s body, she learns being older doesn’t magically fix everything—and that the person she really needed was right there all along.
Hitch was so much fun because it was a rom-com that featured men as the ones unlucky in love, and cast the incredibly charming Will Smith as one of those men. Smith plays Hitch, a dating consultant who teaches men how to woo women—but could use a few lessons in how to have a real relationship.
She's the Man (2006)
Loosely based on Shakespeare’s Twelfth Night, this hilarious teen rom-com follows Amanda Bynes as Viola Hastings, who is posing as her twin brother in order to play soccer on the boy’s high school team. She quickly falls for her teammate/roommate, played by a young Channing Tatum—and that’s reason enough for us to watch this movie again.
If you think Disney movies are a little ridiculous in their depictions of romance, then this is the movie for you. Playing with the idea of what would happen if a fairy tale damsel (Amy Adams) were to end up in modern-day New York, this campy comedy perfectly skewers traditional romance tropes while stills leaving room for us to appreciate their magic.
500 Days of Summer (2009)
The breakout indie hit of the decade, 500 Days of Summer is a quirky, adorable tale of love between Tom (Joseph Gordon-Levitt) and Summer (Zooey Deschanel). And though it’s (spoiler alert) more of a breakup story than a love story, it still manages to have a happy ending.
Related: 19 Movies to Watch After a Breakup
Featured still from "500 Days of Summer" via Fox Searchlight Pictures