The Leading Ladies Who Ruled ‘90s Rom-Coms

The 1990s were truly a Golden Age of romantic comedies. But we all know a good rom-com is only as charming as its leading lady. Check out eight of the genre’s most iconic stars—and get ready to make memories with them all over again.

Julia Roberts

Julia Roberts kicked off the decade with the genre-defining classic “Pretty Woman,” a modern Cinderella story about a vivacious sex worker who’s rescued from the streets by handsome businessman Richard Gere (don’t worry…she rescues him right back). Seven years later, she flipped the rom-com script with “My Best Friend’s Wedding,” a rule-breaking comedy about love, longing and unconventional endings. Next came the endlessly charming “Notting Hill,” in which she played a movie star who falls for an adorable British everyman (Hugh Grant). And in 1999, she reunited with her “Pretty Woman” co-star (and director!) in “Runaway Bride.” What a way to bookend the 10 most memorable years in rom-com history.

Where to stream:
“Pretty Woman” – Prime Video
“My Best Friend’s Wedding” – Prime Video
“Notting Hill” – Hulu or Prime Video
“Runaway Bride” – Prime Video

Meg Ryan

If we were to christen a king and queen of ’90s rom-coms, we’d look no further than Tom Hanks and Meg Ryan. This dreamy duo began their partnership in 1990, with the cult comedy “Joe Versus the Volcano,” but it was 1993’s wistfully romantic “Sleepless in Seattle” that launched them both into the realm of rom-com royalty. The Hanks-Ryan trilogy concluded with what is arguably the most ’90s rom-com ever made: the email-centric “You’ve Got Mail.” But lest you think Meg can’t carry a chick flick sans Tom, consider her Parisian romp with Kevin Kline in 1995’s “French Kiss.” We’d also be remiss not to mention her role in one of history’s best rom-coms, the Nora Ephron classic “When Harry Met Sally,” although its 1989 release date means we’re cheating (a little).

Where to stream:
“Joe Versus the Volcano” – HBO Max
“Sleepless in Seattle” – Hulu
“You’ve Got Mail” – HBO Max
“French Kiss” – Currently unavailable on major streaming platforms
“When Harry Met Sally” – HBO Max

Sandra Bullock

This American sweetheart’s rom-com career has spanned at least two decades. If we narrow it down to ’90s faves, the most lovable of the bunch is probably “While You Were Sleeping,” a Christmas-y comedy about a lonely woman who accidentally tricks her comatose crush’s family into thinking she’s his fiancée. But if you’re craving more, check out her turn as a lovable Manic Pixie Dream Bullock in “Forces of Nature” or the partners-in-crime chemistry of “Two If By Sea.”

Where to stream:
“While You Were Sleeping” – Disney+
“Forces of Nature” – Prime Video
“Two If By Sea” – Prime Video

Angela Bassett

True romantic comedy aficionados know that Angela Bassett is an unsung heroine of the genre. You may remember her powerhouse performance in “Waiting to Exhale,” an ensemble dramedy about four unlucky-in-love girlfriends. Bassett’s true rom-com triumph came with 1998’s “How Stella Got Her Groove Back.” The tale of an overachieving single mom’s romance with a much younger man (the impossibly hunky Taye Diggs), “Stella” is both an empowering, irresistible love story and a groundbreaking film that redefined what rom-coms could be.

Where to stream:
“Waiting to Exhale” – Prime Video
“How Stella Got Her Groove Back” – Prime Video

Drew Barrymore

The ’90s were a romantic decade for Barrymore, with her girl-next-door beauty and trademark lisp. Not only did she return to the scene of her high school heartbreak in “Never Been Kissed,” but she brought an unexpected sweetness to the chaotic Adam Sandler Cinematic Universe with her performance in “The Wedding Singer.” And let’s not forget the underrated “Home Fries,” in which she plays a pregnant fast food worker who finds herself in the middle of some off-the-wall family drama… and ends up falling for a lovable Luke Wilson along the way.

Where to stream:
“Never Been Kissed” – Hulu or Prime Video
“The Wedding Singer” – HBO Max
“Home Fries” – Prime Video

Julia Stiles

There is a rom-com so irresistible, so iconic, so utterly timeless that it earned its leading lady a spot on this list based on this film alone. That rom-com is 1999’s “10 Things I Hate About You,” and that lady is Julia Stiles. Set at the fictional Padua High School, this adaptation of Shakespeare’s “The Taming of the Shrew” casts a platform-flip-flop-wearing Stiles opposite the late, great Heath Ledger (in his breakout American role). No early-2000s slumber party was complete without a screening of this sweet, smart, still-fresh teen comedy. Revisiting Stiles’ performance today guarantees you 99 minutes of nostalgic bliss.

Where to stream: Disney+

Cameron Diaz

Cameron Diaz has been capturing hearts since 1994, with her debut role as Jim Carey’s love interest in “The Mask.” Maybe that’s because she somehow manages to seem sweet, approachable and a little silly while also being drop-dead gorgeous. These same qualities also somehow made us root for her to get the guy in “My Best Friend’s Wedding,” even if it meant leading lady Julia Roberts would go home empty-handed. But it’s the 1998 screwball comedy “There’s Something About Mary” that truly made her a rom-com goddess. Whether that flick’s raunchy humor is your cup of tea or not, you’ve got to admit…there’s just something about Cameron.

Where to stream:
“The Mask” – Hulu
“My Best Friend’s Wedding” – Prime Video
“There’s Something About Mary” – Hulu or Prime Video

Alicia Silverstone

Did you think Alicia Silverstone was a rom-com one-hit wonder? You thought wrong! Of course, her most important contribution to the genre is unquestionably “Clueless,” a loose adaptation of Jane Austen’s “Emma” set in an affluent L.A. high school. But Silverstone also shines opposite Benicio del Toro in 1997’s “Excess Baggage,” about a hapless car thief who accidentally kidnaps an attention-starved rich girl. Plus, she closed out the ’90s as the love interest of a guy stuck in the ’60s: Brendan Fraser in the fish-out-of-water comedy “Blast from the Past.” Which is exactly what you’ll get when you watch Silverstone work her quintessentially ’90s magic.

Where to stream:
“Clueless” – HBO Max
“Excess Baggage” – Prime Video
“Blast from the Past” – Hulu

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