Y2K romcoms: 21 films from the genre's last golden age

Weekly collection in the app for the week of May 15, 2026.

Somewhere between 1999 and 2009, Hollywood remembered how to write a meet-cute: Hugh Grant stammered, Sandra Bullock fell over furniture, Renée Zellweger kept a diary. The era's romcoms were formula, but formula executed by stars and scripts that knew exactly what they were doing.

This collection of 21 films ran as the weekly theme in the I Like Movies Discover tab for the week of May 15, 2026, featuring Bridget Jones's Diary. Amélie and My Sassy Girl keep it from being a purely Hollywood list.

The collection

1. Bridget Jones's Diary (2001) Maguire Featured A London thirtysomething resolves to fix her life via diary and lands between a caddish boss and a standoffish barrister; Renée Zellweger made the mess immortal. Cast: Renée Zellweger, Colin Firth, Hugh Grant
2. Notting Hill (1999) Michell A divorced London bookseller spills orange juice on the world's most famous actress and somehow keeps seeing her; charm calibrated to the decimal, with the flatmate of the era. Cast: Julia Roberts, Hugh Grant, Gina McKee
3. Love Actually (2003) Curtis Nine intertwined London love stories in the five weeks before Christmas, from Downing Street to a school pageant; the ensemble Christmas romcom every December argument is about. Cast: Hugh Grant, Alan Rickman, Emma Thompson
4. Amélie (2001) Jeunet A shy Montmartre waitress secretly engineers happiness for everyone around her while dodging her own; whimsical, green-tinted, and the reason a generation moved to Paris. Cast: Audrey Tautou, Mathieu Kassovitz, Rufus
5. Legally Blonde (2001) Luketic Dumped for not being serious, a sorority president follows her ex to Harvard Law out of spite and stays on merit; the rare comedy whose message landed as hard as its jokes. Cast: Reese Witherspoon, Luke Wilson, Selma Blair
6. The Holiday (2006) Meyers A London journalist and an L.A. trailer-maker, both freshly heartbroken, swap houses for Christmas and find replacements on each other's continents; peak comfort cinema. Cast: Cameron Diaz, Kate Winslet, Jude Law
7. Something's Gotta Give (2003) Meyers A sixty-something playboy has a heart attack at his young girlfriend's beach house and falls, against every instinct, for her playwright mother; Keaton and Nicholson sparring as adults. Cast: Jack Nicholson, Diane Keaton, Keanu Reeves
8. The Devil Wears Prada (2006) Frankel An aspiring journalist takes a job as assistant to fashion's most terrifying editor and starts becoming someone her friends do not recognize; Streep rules it in a whisper. Cast: Meryl Streep, Anne Hathaway, Emily Blunt
9. Miss Congeniality (2000) Petrie A graceless FBI agent goes undercover as a beauty-pageant contestant to stop a bomber; Sandra Bullock falling over in an evening gown, elevated to art. Cast: Sandra Bullock, Benjamin Bratt, Heather Burns
10. How to Lose a Guy in 10 Days (2003) Petrie She is writing a column about driving a man away in ten days; he has bet he can make any woman fall for him in the same window; the formula at its most gleaming. Cast: Kate Hudson, Matthew McConaughey, Adam Goldberg
11. Two Weeks Notice (2002) Lawrence A crusading lawyer quits working for her impossible billionaire boss, who then cannot function through her notice period; Bullock and Grant doing screwball at half speed. Cast: Sandra Bullock, Hugh Grant, Dana Ivey
12. Music and Lyrics (2007) Lawrence A washed-up eighties pop idol has three days to write a hit for a teen superstar, and his plant lady turns out to be the lyricist; opens with a flawless fake 80s video. Cast: Drew Barrymore, Hugh Grant, Brad Garrett
13. Hitch (2005) Tennant A professional date doctor who makes awkward men presentable falls for a gossip columnist and finds none of his own techniques work; Will Smith's smoothest star turn. Cast: Will Smith, Eva Mendes, Kevin James
14. Sweet Home Alabama (2002) Tennant A rising New York designer engaged to the mayor's son must first fly home to Alabama and divorce the husband she never mentioned; the culture-clash romcom done sweetest. Cast: Reese Witherspoon, Josh Lucas, Patrick Dempsey
15. 13 Going on 30 (2004) Waters A thirteen-year-old wishes herself grown and wakes at thirty with the career, the closet and none of the memories, discovering who she became; Jennifer Garner sells every beat. Cast: Jennifer Garner, Mark Ruffalo, Judy Greer
16. About a Boy (2002) Weitz A rich London idler invents a son to date single mothers and instead acquires an odd, bullied twelve-year-old who keeps showing up; the Hugh Grant performance with an actual arc. Cast: Hugh Grant, Nicholas Hoult, Toni Collette
17. My Sassy Girl (2001) Kwak A hapless engineering student rescues a drunk girl on the subway and is conscripted into her chaotic, bossy, secretly grieving orbit; the Korean romcom that conquered Asia. Cast: Gianna Jun, Cha Tae-hyun, Kim In-mun
18. The Wedding Planner (2001) Shankman San Francisco's most controlled wedding planner is rescued from a runaway dumpster by a charming doctor, who turns out to be her biggest client's groom. Cast: Jennifer Lopez, Matthew McConaughey, Justin Chambers
19. Definitely, Maybe (2008) Brooks Amid his divorce, a father tells his daughter the story of his three great loves with the names changed, and she has to guess which one is her mother; sturdier than its premise sounds. Cast: Ryan Reynolds, Abigail Breslin, Elizabeth Banks
20. The Proposal (2009) Fletcher A feared Canadian editor facing deportation announces a sudden engagement to her put-upon assistant, and his Alaska family hosts the charade; Bullock and Reynolds, peak bicker. Cast: Sandra Bullock, Ryan Reynolds, Malin Akerman
21. Bridget Jones: The Edge of Reason (2004) Kidron Bridget, finally coupled, invents new catastrophes: jealousy over a leggy colleague, a ski disaster and a Thai prison stint; more of the diary, played broader. Cast: Renée Zellweger, Colin Firth, Hugh Grant

Keep your place

Comfort rewatches deserve tracking too: rate these in I Like Movies and the app learns what an easy evening looks like for you. A new themed collection lands in the Discover tab every Friday.

Questions people ask

What is the best 2000s romcom?

By reputation, Bridget Jones's Diary and Love Actually for the British school, How to Lose a Guy in 10 Days and The Proposal for the Hollywood one. Amélie, if you allow France in.

Why did romcoms fade after this era?

The mid-budget star vehicle stopped making theatrical money in the 2010s, and the genre moved to streaming with smaller casts and smaller scripts. This list covers roughly the last decade when romcoms were event cinema.

The week before: Classic literature on screen: 21 great adaptations. The week after: African cinema: 21 essential films. See every weekly theme, or browse every guide, watch order and comparison.