The 2000s were the last great boom period for theatrical romantic comedies. Studios invested heavily in star driven vehicles, high concept setups, and glossy, big-hearted stories built around actors like Julia Roberts, Sandra Bullock, Reese Witherspoon, and Matthew McConaughey. Streaming had not taken over yet, so romcoms were still major box office draws. The result is a decade packed with comfort-watch classics that defined the early millennium.
Here are the best romantic comedies of the 2000s that still hold up.
Legally Blonde (2001)
Part romcom, part college comedy, and part empowerment story, Legally Blonde became an instant classic thanks to Reese Witherspoon’s pitch-perfect performance as Elle Woods. The film is sharp, warm, and endlessly quotable, with a surprisingly sweet romance that never overshadows Elle’s growth.
Where to watch: Available to stream; sold on physical media and digitally.
Love Actually (2003)
Richard Curtis weaves together multiple love stories across London during the holiday season. The ensemble cast, touching moments, and mix of humor and heartbreak made Love Actually one of the most rewatched romantic comedies of the century. It helped cement the event-style ensemble rom-com as a major trend.
Where to watch: Available to stream; sold on physical media and digitally.
13 Going on 30 (2004)
Jennifer Garner stars as a teenager who wakes up in her thirty-year-old body, leading to a heartfelt story about identity, friendship, and rediscovering childhood romance. Garner and Mark Ruffalo make the central romance feel grounded and emotional despite the magical premise.
Where to watch: Available to stream; sold on physical media and digitally.
The Proposal (2009)
Sandra Bullock and Ryan Reynolds bring sharp comedic timing to this story of a demanding editor who forces her assistant to marry her to avoid deportation. Their chemistry carries the film, and Betty White steals every scene she appears in.
Where to watch: Available to stream; sold digitally.
How to Lose a Guy in 10 Days (2003)
Kate Hudson and Matthew McConaughey headline one of the decade’s most iconic date-night romcoms. The film’s battle-of-wills setup, magazine world satire, and charismatic performances helped it become a massive hit and a cable television staple.
Where to watch: Available to stream; sold on physical media and digitally.
The Holiday (2006)
Nancy Meyers delivers another warm, beautifully designed romantic comedy about two women who swap homes to escape their personal troubles. Kate Winslet, Cameron Diaz, Jude Law, and Jack Black each bring emotional sincerity to a story that blends romance with personal reinvention.
Where to watch: Available to stream; sold on physical media and digitally.
Hitch (2005)
Will Smith plays a dating consultant whose carefully crafted rules collapse when he meets someone he genuinely cares about. The film’s charm comes from Smith’s charisma and his comedic chemistry with Eva Mendes. It is one of the decade’s most rewatchable hits.
Where to watch: Available to stream; sold digitally.
Bridget Jones: The Edge of Reason (2004)
The sequel to Bridget Jones’s Diary may be broader and sillier, but it still delivers plenty of charm. Renée Zellweger, Colin Firth, and Hugh Grant continue their complicated romantic triangle with a mix of humor and self-deprecating warmth.
Where to watch: Available to stream; sold on physical media and digitally.
50 First Dates (2004)
Adam Sandler and Drew Barrymore reunite for a sweet story about a woman with short-term memory loss and the man determined to make her fall in love with him every day. The film balances emotional stakes with trademark Sandler humor, and the ending remains surprisingly touching.
Where to watch: Available to stream; sold on physical media and digitally.
About a Boy (2002)
Hugh Grant delivers one of his best performances as a selfish bachelor who undergoes a slow emotional transformation after forming an unlikely bond with a young boy and his mother. The romance is understated but deeply heartfelt, and the film’s humor is sharp and authentic.
Where to watch: Available to stream.
Why 2000s RomComs Still Matter
The 2000s marked the last era when romantic comedies consistently dominated the box office. The films blended high-concept setups with grounded emotional arcs and relied heavily on charismatic stars to carry the narrative. Many of today’s comfort-watch favorites come from this decade because the stories feel sincere, warm, and optimistic without losing their comedic bite.
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