When we say "1990s," what movie genre pops into your head? It was probably romantic comedy - because these delightful little films that combined humor and heart dominated the box office at the end of the 20th century. Stars like Julia Roberts, Richard Gere, Meg Ryan and Tom Hanks stole scene after scene as the new millennium approached - but which films were the best? The Watch With Us team has ranked the seven best rom-coms from the 1990s. From modern fairy tales to high school comedies, find out why we love these movies now. 7. 'Groundhog Day' (1993) Ironically, we could watch this movie about doing the same thing over and over again a million times. Bill Murray stars as Phil Connors, a cynical weatherman who becomes trapped in a time loop when sent to report on Punxsutawney Phil in Punxsutawney, Pennsylvania, ultimately falling in love with his station's new producer, Rita (Andie MacDowell). Funny, romantic and strangely philosophical, Groundhog Day is a story that somehow never gets old - and it might just make you appreciate the simple joys of life a little more. It's an unforgettable part of the 1990s rom-com canon. Watch Groundhog Day on Netflix. 6. 'Shakespeare in Love' (1998) Next on our list is a journey back to Elizabethan England, where a young upstart named William Shakespeare (Joseph Fiennes) is hoping to impress Queen Elizabeth I (Judi Dench) with his new comedy: Romeo and Ethel, the Pirate's Daughter. As you might suspect, not everything goes according to plan. Viola de Lesseps (Gwyneth Paltrow), a noblewoman who loves the theater, disguises herself as a man to audition for the play - and before long, she and Shakespeare fall in love. Beautifully costumed and acted, with plenty of Easter eggs for even casual fans of the Bard, Shakespeare in Love is an epic romance with comedy worthy of the playwright in its title. It's the rare Best Picture winner that still feels as fresh as ever. Rent Shakespeare in Love on Amazon Prime Video or Apple TV+. 6 Must-Watch Rom-Coms on Prime Video Right Now (September 2025) 5. 'The Parent Trap' (1998) The Parent Trap doesn't really start to feel like a romantic comedy until the last third of the film, but once the romance hits, it hits hard. When twins Annie and Hallie (both played by Lindsay Lohan) discover that they were separated at birth by their divorced parents, their mission becomes clear: they need to find out exactly how they fell in love and make it happen all over again. And when the twins finally do get Elizabeth James (Natasha Richardson) and Nick Parker (Dennis Quaid) to reunite in person, the sparks certainly fly. A charming story about second chances, The Parent Trap proves that love - and family - always find a way. Watch The Parent Trap on Disney+. 30 of the Most Romantic Movies of All Time: 'The Notebook' and More 4. 'You've Got Mail' (1998) In 1937, a Hungarian playwright named Miklós László wrote a play called Parfumerie about two colleagues who can't stand each other in real life but fall in love through anonymous letters. That play has been adapted countless times - and in the '90s, email was the hottest new way to tell the story. In this now-charming time capsule, You've Got Mail follows Kathleen Kelly (Meg Ryan), the owner of a small bookstore, and Joe Fox (Tom Hanks), the heir to a large book chain empire. While Joe's business starts to edge Kathleen's out, the two connect in an AOL chatroom (oh, the '90s!) and begin to fall in love. Dated details aside, the memorable score and Nora Ephron's romantic script make You've Got Mail completely timeless - it's a digital fairy tale that still feels warm and cozy. Rent You've Got Mail on Amazon Prime Video or Apple TV+. 3. 'Clueless' (1995) Inspired by Jane Austen's Emma, Clueless trades petticoats for plaid skirt sets and England for Beverly Hills, following Cher Horowitz (Alicia Silverstone) as she meddles in the love lives of everyone from her teachers (Wallace Shawn and Twink Caplan) to her new classmate Tai (Brittany Murphy). But can she stop ignoring her own heart long enough to realize she's "totally, butt-crazy in love" with Josh (Paul Rudd)? Full of iconic lines, unforgettable fashion and tons of heart, Clueless is a smart and heartfelt movie wrapped up in a vapid package - a perfect blend of satire and sincerity. Watch Clueless on Hulu, Pluto, Netflix or Paramount+. 16 Must-Watch Rom-Com Movies on Hulu Right Now (September 2025) 2. 'Pretty Woman' (1990) You can't have a '90s rom-com list without a Julia Roberts and Richard Gere movie, so let's stay in Beverly Hills with Pretty Woman for a minute. Roberts plays Vivian Ward, the ultimate "hooker with a heart of gold," who becomes a long-term "date" for Edward Lewis (Gere) while he's visiting Los Angeles. A makeover and many deep chats lead the two unlikely lovers to fall for each other, but social class and money divide them. Endlessly quotable and full of charm, Pretty Woman remains one of the most iconic Cinderella stories in Hollywo