The 1990s were the peak of the romantic comedy. Studios invested heavily in the genre, new stars broke out almost overnight, and audiences embraced stories that blended sincerity with sharply written humor. Tom Hanks and Meg Ryan became the decade’s defining duo, Julia Roberts became a global star, and the modern romcom formula reached its most polished form. The result is one of the strongest and most rewatchable decades the genre has ever seen.
Here are the best romantic comedies of the 1990s that still stand as fan favorites.
Pretty Woman (1990)
Julia Roberts and Richard Gere headline this modern Cinderella story about a wealthy businessman and a Hollywood sex worker whose arrangement turns into a genuine connection. Roberts became an instant superstar, and the film’s mix of glamour, humor, and heart made it a defining romcom of the decade.
Where to watch: Available to stream; sold on physical media and digitally.
Sleepless in Seattle (1993)
Tom Hanks and Meg Ryan helped reinvent the genre with a romantic comedy built on longing rather than direct interaction. Inspired by classic Hollywood melodrama, the story follows two strangers drawn together across the country by fate and late night radio.
Where to watch: Available to stream; sold on physical media and digitally.
Four Weddings and a Funeral (1994)
Hugh Grant became a household name thanks to his charming performance in this British ensemble comedy about friendship, missed chances, and unlikely romance. Its mix of humor and warmth helped kick off a wave of British romcoms that defined the decade.
Where to watch: Available to stream; sold on physical media and digitally.
Notting Hill (1999)
Julia Roberts and Hugh Grant star in a story about a famous actress who falls for a shy bookshop owner. The film’s gentle humor, memorable set pieces, and the chemistry between its leads make it one of the most beloved romcoms ever made.
Where to watch: Available to stream; sold on physical media and digitally.
10 Things I Hate About You (1999)
A sharp teen update of Shakespeare’s The Taming of the Shrew, starring Julia Stiles and Heath Ledger. Ledger’s charismatic performance and the film’s clever script helped it become one of the most enduring teen romcoms of the era.
Where to watch: Available to stream; sold on physical media and digitally.
Buena Vista Pictures
While You Were Sleeping (1995)
Sandra Bullock stars as a lonely transit worker who is mistaken for the fiancée of a man in a coma. When she begins to fall for his brother instead, the story becomes a sweet, heartfelt look at family, connection, and choosing where you belong.
Where to watch: Available to stream; sold on physical media and digitally.
You’ve Got Mail (1998)
The third Hanks and Ryan collaboration updated The Shop Around the Corner for the AOL era. The film captures a moment in time when email felt new and full of possibility, and the chemistry between the leads remains as charming as ever.
Where to watch: Available to stream; sold on physical media and digitally.
My Best Friend’s Wedding (1997)
Julia Roberts plays against type as a woman trying to sabotage her best friend’s wedding. The film’s bold choice to avoid a traditional romcom ending gave it a refreshing twist, and Roberts’ chaotic performance is still one of her most memorable.
Where to watch: Available to stream; sold on physical media and digitally.
Clueless (1995)
Alicia Silverstone stars in this smart, stylish update of Jane Austen’s Emma. The film became a cultural phenomenon thanks to its sharp writing, fashion, and unexpectedly sweet romantic arc between Cher and Josh. It remains a high point of 90s teen cinema.
Where to watch: Available to stream; sold on physical media and digitally.
As Good as It Gets (1997)
Jack Nicholson and Helen Hunt star in this offbeat romance between a misanthropic writer and a struggling waitress. Their complicated, slow-building relationship helped the film earn multiple Oscars and showed that romcoms could be both comedic and dramatically rich.
Where to watch: Available to stream; sold on physical media and digitally.
Why 1990s RomComs Still Matter
The 1990s produced the romcoms that people revisit most. The decade perfected the balance of charm, conflict, and resolution that defines the genre. Its films were built on strong characters, tight scripts, and lead performances that became cultural landmarks. The 90s romcom still sets the standard for what audiences expect from the genre today.
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Image Suggestions
- Featured image: Collage of Sleepless in Seattle, Pretty Woman, and Notting Hill.
Alt text: “Collage of 1990s romantic comedies including Sleepless in Seattle, Pretty Woman, and Notting Hill.” - Sleepless in Seattle – Tom Hanks and Meg Ryan on the Empire State Building.
Alt: “Tom Hanks and Meg Ryan at the top of the Empire State Building in Sleepless in Seattle.” - Pretty Woman – Julia Roberts and Richard Gere walking down Rodeo Drive.
Alt: “Julia Roberts and Richard Gere walking together in Pretty Woman.” - 10 Things I Hate About You – Heath Ledger singing on the bleachers.
Alt: “Heath Ledger performing in the stadium scene in 10 Things I Hate About You.” - Notting Hill – Julia Roberts and Hugh Grant in the bookstore.
Alt: “Julia Roberts and Hugh Grant inside the bookstore in Notting Hill.” - While You Were Sleeping – Sandra Bullock with the Lawson family around the dinner table.
Alt: “Sandra Bullock sitting with the family in While You Were Sleeping.”
