Quite possibly the golden era of romantic comedies, the 90s left viewers swooning for epic love stories. This decade produced rom-com icons and couples that audiences still ship for today, a feat that has yet to be replicated successfully since. Sure, these features set unrealistic expectations for high school romances, will-they-won't-they, and the all too dreamy "take me back, I love you" at the end just before the credits roll.
Never Been Kissed PG-13 Comedy Romance Release Date April 9, 1999 Cast Drew Barrymore , David Arquette , Michael Vartan , Leelee Sobieski , Jeremy Jordan , Molly Shannon , Garry Marshall , John C. Reilly Runtime 107 Minutes Watch on Starz There's Something About Mary is stupid funny, brought to the screen by the directors of Dumb and Dumber. The movie is heavily rooted in puerile-style comedy, using a love story as a driving justification but featuring plenty of the crass, gross-out humor that characterized the Farrelly Brothers' early career. An R-rated comedy, it was a hit with critics and audiences that catered to a variety of viewers in one sitting.
6 'You've Got Mail' Director: Nora Ephron Directed by the behind-the-camera rom-com queen Nora Ephron, You've Got Mail is a 90s-defining romantic comedy. It features two of the generation's biggest stars, Meg Ryan and Tom Hanks, as they break the golden rule in romance: don't fall for the enemy. A bookshop owner, Kathleen , unknowingly engages in an internet romance with a man she hates, Joe , the man who happens to be trying to run her out of business.
Clueless pokes fun at the absurdity of teenage melodrama and the mentality of a Beverly Hills high school. An adaptation of Jane Austen's Emma, the 90s soft satirical take is easily digestible decades later. In true rom-com fashion, it's the story of a girl obsessed with everything of material importance instead of what actually matters.
There's no substitution for masterful romantic chemistry, which is why Notting Hill is not only one of the most rewatchable 90s rom-coms but one of the best rom-coms ever. Roberts and Grant are magic in this BAFTA-winning flick. Grant is a household name in rom-com and British cinema, while Roberts is rom-com royalty, arguably cinema's greatest leading lady in the genre.