The 1990s were basically the height of the romantic comedy. The decade gave us bookstore romance, fake relationships, and best friends falling for each other. The leads were so ridiculously charming that they somehow made even predictable stories work. Stars like Julia Roberts, Meg Ryan, Tom Hanks, and Hugh Grant became synonymous with the genre. These movies are funny, romantic, and best of all, rewatchable.
1. Pretty Woman (1990)
Pretty Woman turned Julia Roberts into one of the biggest movie stars in Hollywood. She plays Vivian, a sex worker hired by wealthy businessman Edward Lewis, played by Richard Gere, to be his arm candy at social events. What begins as a business arrangement that grew out of boredom gradually turns into a genuine connection. The opulent lifestyle is fun to watch, with luxury hotels, designer clothes, and one extremely satisfying shopping scene. Roberts’ charm keeps the movie sweet despite its somewhat controversial premise. More than three decades later, it is still one of the most popular romantic comedies ever made.
2. Sleepless in Seattle (1993)
Sleepless in Seattle creates an unforgettable romance between two people who barely spend any time together. Tom Hanks plays a widowed father whose son calls a matchmaking radio show hoping to find him a new wife. Meg Ryan plays a woman across the country who becomes fascinated by his story. Their paths just barely miss each other several times before they finally come together at the Empire State Building. The movie leans heavily into the idea that certain people are destined to meet, even when everything seems to keep them apart. It’s sentimental and charming, with the kids pulling the strings adding a sweet element. And it gave us everyone’s favorite rom-com duo, Hanks and Ryan.
3. Four Weddings and a Funeral (1994)
Four Weddings and a Funeral turned Hugh Grant’s British charm into an entire rom-com subgenre. Grant plays Charles, a single man who keeps running into an American woman named Carrie at weddings and other major events. Their timing is always terrible, which keeps their relationship complicated. The supporting characters are funny and memorable, giving the story extra warmth. Its success gave wings to a wave of British romantic comedies.
4. Clueless (1995)
Clueless may be remembered as a teen comedy, but romance is at the heart of its story. Alicia Silverstone plays Cher Horowitz, a wealthy Beverly Hills teenager who considers herself an expert matchmaker despite being completely clueless about her own love life. After several failed tries at controlling everyone else’s relationships, she realizes the person she actually wants. And he has been right in front of her the whole time. The movie’s fashion, slang, soundtrack, quotable dialogue, and characters turned it into a big piece of 1990s pop culture.
5. Jerry Maguire (1996)
Jerry Maguire mixed romance with career drama and some still frequently quoted lines. Tom Cruise plays a successful sports agent whose career falls apart after he suddenly develops a conscience about what he does for a living. Renée Zellweger’s Dorothy is the one person who believes in him when he goes out on his own, and their professional relationship quickly becomes something more. It isn’t a fairytale romance, as their relationship is messy and imperfect. The movie gave audiences the extremely sweet lines “You complete me” and “You had me at hello.”
6. My Best Friend’s Wedding (1997)
My Best Friend’s Wedding took the familiar rom-com and gave it a clever twist: its heroine is actually trying to break up someone else’s wedding. Julia Roberts plays Julianne, who suddenly realizes she’s in love with her best friend after he announces his engagement. She spends the movie trying to win him over him and run off the fiancé, but she eventually realizes that she may not be the person he’s supposed to end up with. Cameron Diaz is the super sweet perfect bride Julianne really wants to hate. The bittersweet ending isn’t predictable, which sets it apart from other rom coms.
7. You’ve Got Mail (1998)
Tom Hanks and Meg Ryan reunite once again. This is surely one of the defining romantic comedies of the late 1990s. The two play rival bookstore owners who dislike each other face to face while unknowingly falling in love through anonymous emails online. Using the Internet in this way was relatively new at the time and it now feels like a time capsule of the late ’90s. Audiences were happy to see that the chemistry between the leads hadn’t faded at all. The movie creates atmosphere with cozy New York bookstores, coffee shops, and autumn streets that make every scene feel like a warm blanket. Its old-fashioned romance mixed with then-modern technology worked perfectly. It’s one of the easiest rom coms to rewatch.
8. 10 Things I Hate About You (1999)
10 Things I Hate About You was a modern take on Shakespeare’s The Taming of the Shrew. It moved the classic story to an American high school and created one of the most popular teen romances of the decade. Heath Ledger plays Patrick, who is secretly paid to try to date the independent Kat, played by Julia Stiles. Naturally, the fabricated relationship becomes real, just before she realizes the farce, setting up a very familiar rom com storyline, but one with a fresh spin. Ledger’s stadium performance of “Can’t Take My Eyes Off You” was a very romantic moment. The sharp writing and chemistry between the cast both made this one standout.