Top 10 Classic Romantic Comedies from the 90s You Must Watch Before Turning 20

This time, the beloved Julia Roberts stars alongside a young Cameron Diaz at the start of her career. The film follows Julianne (played by Julia Roberts), a woman still holding onto the hope of being with her best friend from school, who suddenly gets the shocking news that he is engaged and needs her help with the wedding preparations.

Julianne tries everything to sabotage the wedding and break up the couple in an attempt to win back her old flame, but along the way, she comes to realize that she has changed as well.

In this unique romantic comedy, Adam Sandler and Drew Barrymore team up to tell the story of Robbie, a wedding singer, and Julia, a waitress. Robbie was once a promising musician in high school, but after his dreams of becoming a rock star fall apart, he returns home to perform at weddings and other events. One day, Robbie is set to get married himself, only to be left heartbroken when the bride doesn't show up. What he doesn’t realize is that someone who has been by his side all along has quietly been in love with him.

'10 Things I Hate About You' is loosely based on Shakespeare's 'Taming of the Shrew' and features a cast of rising stars from the late 90s, including Julia Stiles, Joseph Gordon-Levitt, and Heath Ledger.

This romantic comedy revolves around a group of high school students navigating love triangles and relationships, culminating in a memorable prom night — the most important event in a typical American student's life.

With the internet becoming more widespread in the 90s, it's no surprise that Hollywood filmmakers produced a romantic comedy about two people who meet online. The twist is that these seemingly perfect matches are actually business rivals in real life. Meg Ryan plays Kathleen, the owner of a small bookstore, who faces tough competition when Joe (Tom Hanks), the owner of a large bookstore chain, opens a new store right across the street.

The film cleverly captures the growing presence of the internet in everyday life, exploring how people began using it to find love and how the rise of big business was beginning to swallow up the little guy.

It's safe to say that Julia Roberts was the shining star of 90s romantic comedies, as she continuously took the lead in hit films, winning the hearts of audiences everywhere. In 'Notting Hill', Roberts plays Anna Scott, a famous Hollywood actress who unexpectedly falls for William (Hugh Grant), a humble bookstore owner, during a trip to the UK for a film shoot.

Their vastly different social standings create a major obstacle, but ultimately, nothing can stand in the way of true love, especially when it’s mutual and heartfelt.

In this film, Drew Barrymore stars as Josie, a 25-year-old reporter looking for a breakthrough in her career. She is assigned a quirky task: to go undercover as a high school student to conduct research and write an article about it.

As Josie tries to navigate the challenges of high school life in the modern era, the situation quickly spirals into awkward and funny moments, especially since she has no fond memories of her own teenage years. Eventually, Josie falls for her teacher, Sam (played by Michael Vartan), who mistakenly believes she's just another high school girl.

'American Pie' is not only a fantastic romantic comedy, but it also played a key role in introducing the raunchy, awkward high school humor that we now see in many modern comedies.

With a cast of breakout stars including Jason Biggs, Sean William Scott, Tara Reid, and Alyson Hannigan, this film became one of the most iconic teen comedies of all time, capturing the essence of 90s humor with its blend of crude jokes and heartwarming moments.

In the early 90s, Julia Roberts rose to stardom with her unforgettable performance alongside Richard Gere in 'Pretty Woman', which remains one of the most beloved romantic comedies to this day.

Richard Gere plays Edward Lewis, a wealthy businessman who hires Vivian Ward (played by Julia Roberts), a prostitute, to be his companion at various events. At the time, Edward was unable to find someone suitable for a long-term relationship, so he opts for Vivian as a temporary partner. Over time, their connection grows, leading to a fairy tale ending where the 'prince' rescues the 'princess'.

In this heartwarming film, Tom Hanks plays Sam Baldwin, a widowed father of an 8-year-old boy, who relocates to Seattle in search of a fresh start after the tragic death of his wife. Initially, Sam has no intentions of finding love again, but on Christmas Eve, his son persuades him to participate in a radio show to share his grief and thoughts with the world.

The broadcast leads to a flood of calls and letters from women across the country, all eager to date Sam. Among them is Annie (Meg Ryan), a woman who is engaged but wishes her own relationship could be as romantic as Sam's story. The iconic scene where they finally meet atop the Empire State Building remains one of the most memorable moments in film history.

In this charming rom-com, Sandra Bullock stars as Lucy, a woman secretly in love with Peter. After saving him from a mugging, she accidentally causes him to fall into a coma. When she confesses, 'I was going to marry him' at the hospital, the staff misinterprets her words and believes she is Peter's fiancée. As his family arrives, they are introduced to Lucy as his soon-to-be wife.

Things get even more complicated as Lucy finds herself falling for Peter's brother, Jack. When Peter wakes up from his coma, he is told by his family that he must have lost his memory, as he doesn’t remember Lucy as his fiancée.