The 1990s were a special time for romantic comedies. Actresses like Julia Roberts, Meg Ryan, and Drew Barrymore reigned supreme and took over our screens as America's sweethearts. Rom-coms have a way of capturing the human heart and make viewers feel like anything is possible in the romance department.
Kind of like when Annie Reed and Sam Baldwin fell in love from afar in Sleepless In Seattle or when Kat Stratford fought against her better judgement and fell for the school's bad boy, Patrick Verona, in 10 Things I Hate About You. In all of these movies, there's plot twists, funny banter, top '90s actors, and a whole lot of romance.
Sleepless In Seattle
In 1993, Sleepless in Seattle brought together Tom Hanks as Annie Reed and Sam Baldwin. After Sam loses his wife, he's left to raising his son Jonah alone. But after Jonah calls a radio talk show to talk about his dad's loneliness and refusal of moving on, Annie Reed can't help but fall for this single dad in Seattle.
She writes a letter to Jonah and Sam and urges them to meet her on Valentine's Day night on top of the Empire State Building. After a few comedic mishaps, the two finally meet in the Big Apple and the rest is written in rom-com history.
Pretty Woman
Pretty Woman is a '90s classic with Julia Roberts and Richard Gere as Vivian and Edward, respectively. Vivian was a bright and beautiful woman who made her money as a prostitute, but when wealthy businessman Edward comes to her block, the two begin a unique partnership that surprises them both.
Richard hires Vivian to be his new girlfriend but the two accidentally fall in love. Vivian became the perfect cinematic rags to riches character and was full of confidence and sassy one-liners that impressed— and softened— Edward.
There's Something About Mary
Cameron Diaz and Ben Stiller were the next unforeseen rom-com partners in There's Something About Mary. After coming out in 1998, fans fell in love with Mary (Diaz) just like Ted and all her other friends did. One scene that fans still talk about today is when Mary puts something in her hair that she thinks is hair gel, though it is something else entirely.
Nevertheless, a story about childhood friends coming together and finding love years later really resonated with fans, and Mary and Ted's love story is ultimately a sweet one despite the gross-out humor that surrounds it.
As Good As It Gets
Jack Nicholson and Helen Hunt had all eyes on them in 1998's As Good As It Gets. Nicholson played a novelist named Melvin Udall who has major OCD and has fallen victim to its controlling ways. He goes to the same diner every morning, sits in the same booth, and orders the same thing with his favorite waitress, Carol Connelly (Hunt).
Carol is the only woman who can stand Melvin, which does not go unnoticed by him. The two enter a unique entanglement but it's not without its complications. Both Nicholson and Hunt received Academy Awards for their performances.
10 Things I Hate About You
10 Things I Hate About You launched the careers of many of its stars in 1999. The movie was based on Shakespeare's Taming of the Shrew, reworked in a modernized way.
In the movie, sisters Kat (Julia Stiles) and Bianca (Larissa Oleynik) are complete opposites in high school and run in different crowds. But when Bianca's dad decides she can only go out when Kat comes along, a guy name Cameron (Joseph Gordon-Levitt) comes up with a plan. If Patrick (Heath Ledger) is able to persuade Kat to date him, he'll be paid. Of course, Kat and Patrick fall for each other, but things get complicated when she finds out about the bet.
Jerry Maguire
Jerry Maguire is filled with memorable scenes and lines that are still talked about today. With an all-star line up of actors (Tom Cruise, Renée Zellweger, Cuba Gooding Jr., et al), the 1996 movie blended the genres of sports movie and rom-com.
When Jerry Maguire (Cruise) is fired from his job as a prominent sports agent for suddenly developing a conscience, he starts his own agency with Dorothy Boyd (Zellweger) by his side. Together, the two find themselves in a romance while trying to make their newest business venture work with their only client, played by Cuba Gooding Jr., who won an Oscar for the role.
Notting Hill
Julia Roberts proved herself a rom-com goddess in the 1999 film Notting Hill. Starring alongside Hugh Grant as bookseller Will Thacker, Roberts plays popular actress Anna Scott. The two enter this spur-of-the-moment romance that both weren't expecting and it brings both happiness and dismay to their lives.
With Anna being a high-profile actress, their secret romance hits a speedbump when her ex-boyfriend comes to London, and again when one of Will's friends leaks their romance. To this day, is one of the best romance stories of any decade.
Never Been Kissed
Never Been Kissed is one of the best movies of Drew Barrymore's career. The 1999 film was about a copy editor named Josie Geller (Barrymore) who went undercover as a high school student to do a story on life as a teenager. Funny enough, Josie finds that the experience mirrors her old high school days as she once again is a geek who tries to become popular.
Along the way she falls for her teacher Sam Coulson, who has no idea she's actually an adult woman pretending to be a child. Josie eventually lets her true identity be known along with the fact that she's never been kissed, which of course Sam eventually rectifies for her.
You've Got Mail
You've Got Mail is another Meg Ryan and Tom Hanks hit. Ryan plays Kathleen Kelly who owns a local book shop. She becomes bored in her relationship and begins an online friendship with a guy named Joe Fox.
Kathleen and Joe realize they both have feelings for each other but can't agree to meet in person. Ironically, the two have actually met in person, but as competitors. Fox is in charge of a corporate book store that could take Kathleen's out of business. Joe eventually finds out who Kathleen really is and their complicated relationship takes its toll.
Picture Perfect
Jennifer Aniston is another '90s heartthrob who took over screens after the success of Friends. In 1997, she starred alongside Jay Mohr in Picture Perfect. Aniston plays advertising exec Kate who would do anything to be promoted. However, her boss doesn't think she's stable enough.
To prove that she's stable and mature, she hires a man named Nick to be her fiancé. As is the case is most rom-coms, their fake romance becomes real and fans rooted for them to pull through.
