Can You Name These 1990s Romantic Comedy Movies?

By: Khadija Leon
Image: Warner Bros

About This Quiz

Romantic comedies, sometimes referred to as rom-coms or romedies, as the name suggests, are a combination of romantic and comedy films. It is properly defined as a genre of movies whose humorous plotline is centered around one or more romantic themes.  It often focuses on true love and the obstacles people face in order to obtain it, all the while packed with laugh-out-loud moments. 

Some of the most popular romantic comedies to come out of that decade include "10 Things I Hate About You," "There's Something About Mary," "You've Got Mail," "Four Weddings and a Funeral," "Never Been Kissed," "As Good as It Gets," and "It Could Happen To You." They each made millions at the box office and many of them are listed as some of the classics. 

How well do you know the romantic comedies which came out in the 1990s? Were you around to see when they were released or did you only just begin watching them, making you an instant fan? Well if you think you are an expert in the field and that no one can school you on these classics, then this is the quiz you need to take in order to test that knowledge! 

"10 Things I Hate About You" is a 1990 American romantic comedy which was loosely based on the 16th century Shakespeare tale, "The Taming of the Shrew." Starring Julia Stiles, Heath Ledger and Joseph Gordon Levitt, the movie retells the story in a high school setting.

"Pretty Woman" is a 1990 American romantic comedy film starring Richard Gere and Julia Roberts. It's about a Hollywood prostitute who is hired by a rich businessman to be his escort to different business and social events. The two slowly begin to fall for one another.

"Beautiful Girls" is a 1996 American romantic comedy film with an all-star cast that includes Matt Dillon, Lauren Holly, Natalie Portman, Timothy Hutton, and Uma Thurman. It follows a group of people all at crossroads in their lives. By the end of the movie, they figure out what they want.

"Emma" is a 1996 romantic comedy film which was based on the 1815 novel with the same name and written by Jane Austen. It stars Gwyneth Paltrow as the title character and Jeremy Northman as her love interest.

"Notting Hill" is a 1999 romantic comedy starring Julia Roberts, Hugh Grant, and Ethan Chambers. Set in Notting Hill, London, after which the movie was named, it follows a bookshop owner whose life is forever changed after meeting a famous film star.

There’s Something About Mary is a 1998 American romantic comedy film starring Cameron Diaz as the title character. It also features Matt Dillon, Ben Stiller, Lee, Evans, and Chris Elliot – all men who are in love with her.

"Boomerang" is a 1992 American romantic comedy film which stars Eddy Murphy as Marcus Graham, a womanizing and arrogant advertising executive who gets a taste of his own medicine when his new female boss is hired.

"Four Weddings and a Funeral" is a 1994 British romantic comedy film which followed the adventures of Charles (played by actor Hugh Grant) and his friends through different social events.

"You've Got Mail" is a 1998 American romantic comedy film starring Meg Ryan and Tom Hanks that was based on the play, Parfumerie, by Miklós László. It follows the two who are involved in an online romance but are unaware that the companies for which they work are rivals.

"Never Been Kissed" is a 1999 romantic comedy film starring Drew Barrymore as a copy editor working for the Chicago Sun-Times who goes undercover at a high school to make parents more aware of the things going on there.

"Frankie and Johnny" is a 1991 American romantic comedy adapted from the off-Broadway play, "Frankie and Johnny in the Clair de Lune." It stars Al Pacino and Michelle Pfeiffer in their first film together since "Scarface" in 1983.

"American Pie" is a 1999 American film and the first of its series which follows five best friends and students of East Great Falls High. They all make a pact to lose their virginity before they graduate from high school.

"Father of the Bride" is a 1991 American romantic comedy film and the remake of a 1950’s film with the same name. Starring Steve Martin, Dian Keaton, and Kimberly Williams, the movie follows a man who does not want to give his daughter away to be married.

"Drive Me Crazy" is a 1999 American romantic comedy film which was based on Todd Strasser’s novel, "How I Created My Perfect Prom Date." Starring Melissa Joan Hart and Adrian Grenier, the two plot to date each other to make their crushes jealous but end up falling for each other instead.

"As Good as It Gets" is a 1997 American romantic comedy film which stars Jack Nicholson – a novelist, Helen Hunt – a single mother, Greg Kinnear - an artist, and a series of characters whose lives all intertwine in some way. Nicholson and Hunt both received awards for their roles in the movie.

"Before Sunrise" is a 1995 American romantic comedy film which follows an American young man named Jesse and a young French lady named Céline who meet on a train which disembarks in Vienna where they spend the night in the city together.

"While You Were Sleeping" is a 1995 American romantic comedy film which stars Sandra Bullock as a fare transit collector named Lucy and Bill Pullman as a commuter and the relative of someone she saved. Bullock received a Golden Globe nomination for her role in the movie.

"Chasing Amy" is a 1997 American romantic comedy which stars Ben Affleck, Jason Lee and Lauren Adams. It is centered around the life of Affleck’s character, who is in love with a bisexual woman, much to the disapproval of his best friend.

"It Could Happen to You" is a 1994 American romantic comedy based on the real-life events of a New York police officer who won the lottery and decided to split his winnings with a waitress. Nicolas Cage and Bridget Fonda took on the roles of those characters.

"Jerry Maguire" is a 1996 American romantic comedy film which stars Tom Cruise, Renée Zellweger, and Cuba Gooding Jr. The movie was inspired by the story of sports producer Leigh Steinberg, who acted as the technical consultant for the crew.

"Ever After" is a 1998 romantic comedy film which was inspired by the Disney fairy tale, Cinderella. Starring Drew Barrymore, Angelica Huston, and Jeanne Moreau, it tells the story of a woman who is forced into servitude after the death of her father.

"French Kiss" is a 1995 romantic comedy film which starred Meg Ryan and Kevin Kline. It tells the story of a woman who flies to France to confront her cheating fiancé but finds herself in trouble when she is unwillingly used to smuggle a stolen diamond necklace.

"Groundhog Day" is a 1993 American romantic comedy film starring Bill Murray as a television weatherman who gets stuck in a time loop while coving the events of the annual Ground Hog Day celebration.

"Shakespeare in Love" is a 1998 romantic comedy period drama film which brings to life the fictionalized love affair between William Shakespeare (played by Joseph Fiennes) and Viola de Lesseps (played by Gwyneth Paltrow.)

"Clueless" is a 1995 American romantic comedy film set in present-day Beverly Hills. It starred Alicia Silverstone, Paul Rudd, Brittany Murphy, and Stacy Dash as the group of teenagers.

"Doc Hollywood" is a 1991 American romantic comedy based on the book, What? Dead…Again?," by Neil B. Shulman. It stars Michael J. Fox as a young surgeon alongside Woody Harrelson, Bridget Fonda, and Julie Warner.

"Housesitter" is a 1992 American romantic comedy film about a waitress who is also a con artist (played by Goldie Hawn), who charms her way into the life of a struggling architect (portrayed by Steve Martin) by claiming to be his wife.

"My Best Friend’s Wedding" is a 1997 American romantic comedy film which starred Rupert Everett, Dermot Mulroney, Cameron Diaz, and Julia Roberts. It follows two friends who decide to marry each other if they are both single by the time they are 28 years old. But things change when one of them is engaged to another person.

"She’s All That" is a 1999 American romantic comedy which is a modern adaptation of the play, "Pygmalion," and the 1964 film, "My Fair Lady." It starred Rachel Leigh as a dorky teen who was bet on to become prom queen by Freddie Prinze Jr.’s character and their friends.

"The Wedding Singer" is a 1998 romantic comedy film and one of the many films where Adam Sandler and Drew Barrymore starred alongside each other. In this film, Sandler was a wedding singer, and Barrymore was the waitress with whom he falls in love.

"Runaway Bride" is a 1999 American romantic comedy which stars Julia Roberts and Richard Gere. Roberts plays the runaway bride who has left countless men at the altar. Gere is the writer trying to report the story!

"One Fine Day" is a 1996 American romantic comedy film which was named after the 1963 song, “One Fine Day,” by The Chiffons. It starred Michelle Pfeiffer and George Clooney as two single parents who must watch each other’s children for a day while working in New York.

"Can’t Hardly Wait" is 1998 American film which stars an ensemble cast including Jennifer Love Hewitt, Ethan Embry, Seth Green, Charlie Korsmo and Lauren Ambrose. It follows the cast at a high school graduation and through the events that unfold that night that will forever impact their futures.

"Fools Rush In" is a 1997 American romantic comedy which stars Matthew Perry as an architect who is sent to Las Vegas to supervise the construction of a building. During that time, he meets Isabel, played by actress Salma Hayek, and the two are immediately attracted to each other.

"Green Card" is a 1990 romantic comedy film starring Andie MacDowell and Gérard Depardieu. It follows MacDowell’s character, an American woman who gets married to a Frenchman, Depardieu, so that he can remain in the United States.

"Sleepless in Seattle" is a 1993 American romantic comedy which stars Tom Hanks, Meg Ryan, Bill Pullman, Rosie O’Donnell, and Rita Wilson. It follows Hanks’ character, a widower, and his son who moved to Seattle. Hundreds of women begin to write to him after a radio talk show features their story.

"The American President" is a 1995 romantic comedy film which stars Michael Douglas as the President of the U.S., who pursues a relationship with an environmental lobbyist named Sydney Wade while dealing with running an entire country.

"How Stella Got Her Groove Back" is a 1998 American romantic comedy which was adapted from the best-selling novel with the same name by Terry McMillan. The cast includes actors like Regina King, Taye Diggs, Angela Bassett, and Whoopi Goldberg.

"When Harry Met Sally…" is a 1989 American romantic comedy film which stars actors Billy Crystal and Meg Ryan as the title characters. It follows the two through more than 12 years of friendship and chance encounters.

"Edge of Seventeen" is an American 1998 romantic comedy starring Chris Stafford, Tina Holmes and Andersen Gabrych. It is about a talented high school teen who is having difficulty coming to terms with his sexual identity.

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