The 1990s and 2000s were a golden era for romantic comedies, delivering heartfelt moments and laugh-out-loud scenes that still hold up today. Lately, I’ve been dying to see a really good rom-com, but I often find myself going back to the older films from the 90s and 2000s, as the new romantic comedies, in my opinion, fall flat and just don’t have the magic that their predecessors had – is it just me?
If you’re looking to find a fun rom-com to watch with your best friends, your partner, or just on your own in a quiet night in, below is a curated list of the 36 best romantic comedies from the 1990s and 2000s that I hope you enjoy as much as I still do!
1. How to Lose a Guy in 10 Days (2003)
A journalist (Kate Hudson) tries to drive a man (Matthew McConaughey) away for a story, while he bets he can make her fall for him. Chaos and chemistry ensue.
Stream: Paramount+
2. The Proposal (2009)
Sandra Bullock’s high-powered exec forces her assistant (Ryan Reynolds) into a fake engagement to avoid deportation, leading to unexpected sparks.
Stream: Hulu
3. 13 Going on 30 (2004)
A teenager (Jennifer Garner) magically wakes up as a 30-year-old, navigating love and life with a charming boy-next-door (Mark Ruffalo).
Stream: Max
4. Love Actually (2003)
This ensemble rom-com weaves interconnected love stories set during the Christmas season in London, starring Hugh Grant, Emma Thompson, and more.
Stream: Peacock
5. My Big Fat Greek Wedding (2002)
Toula (Nia Vardalos) navigates her overbearing Greek family while falling for a non-Greek (John Corbett) in this indie hit.
Stream: Max
6. Bridget Jones’s Diary (2001)
Renée Zellweger shines as Bridget, caught in a love triangle with a charming cad (Hugh Grant) and a reserved suitor (Colin Firth).
Stream: Amazon Prime Video
7. The 40-Year-Old Virgin (2005)
Steve Carell’s sweet and raunchy journey as a middle-aged virgin finding love with a single mom (Catherine Keener) redefined rom-coms.
Stream: Peacock
8. Ever After (1998)
A variation on the classic story of Cinderella, this version follows Danielle (Drew Barrymore) who is forced to take care of her stepmother and stepsisters before finding true love.
- Stream on Disney+
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9. Maid in Manhattan (2002)
Jennifer Lopez plays a hotel maid mistaken for a socialite by a senatorial candidate (Ralph Fiennes) in this charming romance.
Stream: Netflix
10. 50 First Dates (2004)
Adam Sandler woos Drew Barrymore, who has short-term memory loss, in this heartfelt and funny Hawaiian-set rom-com.
Stream: Hulu
11. The Wedding Planner (2001)
Jennifer Lopez’s wedding planner falls for the groom (Matthew McConaughey) of her biggest client in this classic.
Stream: Netflix
12. Legally Blonde (2001)
Reese Witherspoon’s Elle Woods goes to Harvard Law to win back her ex, but finds her own strength and love along the way.
Stream: Max
13. Knocked Up (2007)
A one-night stand (Seth Rogen and Katherine Heigl) leads to an unexpected pregnancy and a journey to love in this Judd Apatow hit.
Stream: Peacock
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14. Sweet Home Alabama (2002)
Reese Witherspoon’s fashion designer returns to her Southern roots, rekindling an old romance with Josh Lucas.
Stream: Disney+
15. The Princess Diaries (2001)
Anne Hathaway’s Mia transforms from awkward teen to princess, with a side of romance and royal charm.
Stream: Disney+
16. Along Came Polly (2004)
Ben Stiller’s risk-averse analyst meets free-spirited Jennifer Aniston, leading to hilarious and heartfelt moments.
Stream: Peacock
17. Something’s Gotta Give (2003)
Diane Keaton and Jack Nicholson shine in this Nancy Meyers rom-com about finding love later in life.
Stream: Max
18. The Holiday (2006)
Kate Winslet and Cameron Diaz swap homes and find unexpected love with Jude Law and Jack Black in this cozy holiday rom-com.
Stream: Hulu
19. 27 Dresses (2008)
Katherine Heigl’s perpetual bridesmaid finally gets her chance at love with a cynical reporter (James Marsden).
Stream: Disney+
20. Hitch (2005)
Will Smith’s smooth-talking date doctor helps a shy accountant (Kevin James) while falling for a journalist (Eva Mendes).
Stream: Netflix
21. Enchanted (2007)
Amy Adams’ fairy-tale princess lands in modern-day New York, finding real-world love with Patrick Dempsey.
Stream: Disney+
22. The Ugly Truth (2009)
Katherine Heigl and Gerard Butler’s clashing views on love turn into unexpected attraction in this cheeky rom-com.
Stream: Netflix
23. Made of Honor (2008)
Patrick Dempsey realizes he loves his best friend (Michelle Monaghan) just as she gets engaged to someone else.
Stream: Starz
24. Pretty Woman (1990)
A wealthy businessman (Richard Gere) hires a sex worker (Julia Roberts) as an escort, and an unexpected romance blossoms.
- Stream on Hulu; rent on Amazon Prime Video, YouTube TV
25. Clueless (1995)
A wealthy Beverly Hills teen plays matchmaker while navigating her own love life in this Jane Austen-inspired comedy that has the best 90s catch-phrases.
- Stream on Paramount+; rent on Amazon Prime Video, Apple TV+
26. Notting Hill (1999)
A humble bookstore owner falls for a famous actress in this charming British rom-com starring Hugh Grant and Julia Roberts.
- Stream on Max; rent on Amazon Prime Video, Apple TV+
27. 10 Things I Hate About You (1999)
A modern take on Shakespeare’s The Taming of the Shrew, following a teen paid to date a rebellious girl.
- Stream on Disney+; rent on Amazon Prime Video, YouTube TV
28. My Best Friend’s Wedding (1997)
Julia Roberts tries to sabotage her best friend’s wedding when she realizes she’s in love with him.
- Stream on Netflix; rent on Amazon Prime Video, Apple TV+
29. The Wedding Singer (1998)
Adam Sandler plays a heartbroken wedding singer who finds love with a waitress (Drew Barrymore) planning her own wedding. This movie is a must-watch for the wedding songs alone!
- Stream on Amazon Prime
30. While You Were Sleeping (1995)
One of my long-time favorites, a transit worker (Sandra Bullock) is mistaken for a comatose man’s fiancée, leading to a tangled web of romance, which involves his quirky but lovable family.
- Stream on Disney+; rent on Amazon Prime Video, YouTube TV
31. There’s Something About Mary (1998)
A man hires a private investigator to reconnect with his high school crush, leading to chaotic hilarity that is unforgettable!
- Stream on Hulu; rent on Amazon Prime Video, Apple TV+
32. Never Been Kissed (1999)
Drew Barrymore plays a journalist who goes undercover as a high school student and gets a second chance at love.
- Stream on Hulu; rent on Amazon Prime Video, Apple TV+
33. How Stella Got Her Groove Back (1998)
A 40-year-old stockbroker finds romance with a younger man on a Jamaican vacation (count me in!).
- Stream on Hulu; rent on Amazon Prime Video, Apple TV+
34. The Cutting Edge (1992)
A former hockey player (D.B. Sweeney) and a snooty figure skater (Moira Kelly) team up for the Olympics, sparking an unlikely duo.
- Stream on MGM+; rent on Amazon Prime Video, Apple TV+
35. The American President (1995)
Michael Douglas is a widowed president who falls for an environmental lobbyist in Annette Bening, navigating love and politics later in life.
- Rent on Amazon Prime Video, YouTube TV, Apple TV+
36. Sliding Doors (1998)
A woman’s life splits into two alternate realities (Gwyneth Paltrow) based on catching or missing a train, taking an interesting look at how different paths can change fate…or can it?
- Stream on Pluto TV; rent on Amazon Prime Video, Apple TV+
