A Complete List of '90s Rom-Coms to Watch on Repeat

The era that gave us Pretty Woman and Sleepless in Seattle defined the rom-com genre.
Collage of movies Notting Hill and She's All That
Photo: IMDb
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Brittany Barber
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Brittany Barber
The Knot Contributor
  • From top movie picks to celebrity scoops and travel advice, Brittany writes on a wide range of topics for The Knot.
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  • Brittany has a Bachelor of Arts in media and communications studies, along with minors in creative writing, theater studies and music performance....
Updated Oct 29, 2023
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The '90s was a golden era of cinema that introduced us to films that defined the romantic comedy genre, blending love stories with over-the-top humor in the most delightful way. Today, '90s rom-coms continue to grace our screens thanks to the star-studded casts and lighthearted plotlines we all know and love. (Some, even, offering a glimpse into weddings from that decade.)

Whether you're a fan of the charmingly quirky, the swoon worthy, or the hilariously relatable, our editors have gathered a collection of the best rom-coms from the 1990s. These timeless flicks are sure to make you laugh, cry and believe in love all over again. So, snuggle up to your sofa and get ready for a heartfelt exploration through 23 of our favorite '90s romantic comedies.

The Knot's '90s Romance Movie Ranking

If you're looking for the best '90s rom coms, here are our top picks.

Most Nostalgic: Sleepless in Seattle

Funniest: There's Something About Mary

Best Comfort Film: Notting Hill

Most Underrated: While You Were Sleeping

Best Cast: Pretty Woman

Editor's Favorite: 10 Things I Hate About You

Pretty Woman

Pretty Woman movie poster
Photo: IMDb

When it comes to quintessential '90s rom-coms, this Cinderella-like tale takes the cake. It follows the transformation of a vivacious and charming sex worker (Julia Roberts) after meeting and falling in love with a wealthy businessman (Richard Gere).

Release Date: March 23, 1990 | Watch Trailer

Housesitter

Housesitter movie poster
Photo: IMDb

If you're trying to find romantic comedies from the '90s, look no further than this delightful rom com from 1992. When a woman named Gwen (Goldie Hawn) decides to inhabit a vacant house, pretending it's her own, she ropes in the home's architect, Newton (Steve Martin), into her playful ruse.

Release Date: June 12, 1992 | Watch Trailer

Honeymoon in Vegas

Honeymoon in Vegas movie poster
Photo: IMDb

Buckle up for a whirlwind of laughter, love and high-flying adventure with this hilarious '90s rom-com. Starring Nicolas Cage, Sarah Jessica Parker and James Caan, this film follows the quirky journey of a man who must confront his fears when his fiancée catches the eye of a charismatic gambler.

Release Date: August 28, 1992 | Watch Trailer

Strictly Ballroom

Strictly Ballroom movie poster
Photo: IMDb

Directed by Baz Luhrmann, this vibrant '90s rom-com follows dancer Scott (Paul Mercurio) and his journey to break free from tradition in order to embrace his unique style, all while falling for the dazzling Fran (Tara Morice).

Release Date: February 12, 1993 | Watch Trailer

Much Ado About Nothing

Much Ado About Nothing movie poster
Photo: IMDb

Set in a sun-soaked Tuscan villa, this '90s adaptation of Shakespeare's timeless comedy weaves together a witty battle of the sexes as the quick-witted Beatrice (Emma Thompson) and the ever-charming Benedick (Kenneth Branagh) engage in verbal sparring while trying to deny their undeniable attraction.

Sleepless in Seattle

Sleepless in Seattle movie poster
Photo: IMDb

Sleepless in Seattle is a classic '90s romantic comedy that follows the serendipitous love story of Sam (Tom Hanks) and Annie (Meg Ryan). Sam, a recently widowed architect, reluctantly pours his heart out on a radio show, catching the attention of Annie, a journalist from Baltimore.

Release Date: June 25, 1993 | Watch Trailer

So I Married An Axe Murderer

So I Married An Axe Murderer movie poster
Photo: IMDb

This witty rom-com stars Mike Myers, who plays a commitment-phobic poet who suspects his new wife (Nancy Travis) might be a serial killer. With a mix of zany humor and tender moments, this quirky movie offers a darkly hilarious take on the complexities of romantic relationships.

Release Date: July 30, 1993 | Watch Trailer

Four Weddings and a Funeral

Four Weddings and a Funeral movie poster
Photo: IMDb

Directed by Mike Newell and penned by Richard Curtis, this British rom-com follows the charming but perennially unlucky-in-love Charles (Hugh Grant) as he navigates the tumultuous waters of romance within the framework of (yep, you guessed it) four weddings and one funeral.

Release Date: March 9, 1994 | Watch Trailer

While You Were Sleeping

While You Were Sleeping movie poster
Photo: IMDb

Sandra Bullock stars as Lucy, a lonely transit worker in Chicago who saves her secret crush, Peter (Peter Gallagher), from an oncoming train and finds herself mistaken as his fiancée after he falls into a coma. Rather than correct the error, she forms a connection with Peter's endearing family, including his attractive brother Jack (Bill Pullman).

Release Date: April 21, 1995 | Watch Trailer

Jerry Maguire

Jerry Maguire movie poster
Photo: IMDb

Starring Tom Cruise, Jerry Maguire tells the story of a successful sports agent who has an epiphany about the moral implications of his job. He winds up writing something that causes his sudden fall from grace, which leads him to form connections with a spirited single mother named Dorothy (Renée Zellweger) and the charming but eccentric Rod Tidwel (Cuba Gooding Jr.).

Release Date: December 13, 1996 | Watch Trailer

My Best Friend's Wedding

My Best Friend's Wedding movie poster
Photo: IMDb

When it comes to '90s romantic comedies starring Julia Roberts, My Best Friend's Wedding is one of the greats. This film follows the scheming Julianne Potter and her hilarious (and desperate) attempts to win back her best friend, Michael (Dermot Mulroney), who's about to marry the sweet and charming Kimmy (Cameron Diaz).

Release Date: June 20, 1997 | Watch Trailer

Picture Perfect

Picture Perfect movie poster
Photo: IMDb

This '90s rom com stars Jennifer Aniston as Kate Mosley, an advertising executive who's struggling to get ahead in her career and love life. Faced with societal pressure and her workplace's skepticism, she decides to hire a fictional fiancé, Nick (Jay Mohr), to impress her boss.

Release Date: August 1, 1997 | Watch Trailer

The Wedding Singer

The Wedding Singer movie poster
Photo: IMDb

Directed by Frank Coraci, this '90s rom com stars Adam Sandler as Robbie, a charming wedding singer who, after a heartbreak, starts to question love. Drew Barrymore plays Julia, a waitress, engaged to the wrong guy. When Robbie and Julia meet, a heartwarming romance unfolds and Robbie must find a way to win Julia's heart.

Release Date: February 13, 1998 | Watch Trailer

Can't Hardly Wait

Can't Hardly Wait movie poster
Photo: IMDb

With a stellar cast including Jennifer Love Hewitt, Ethan Embry and Seth Green, Can't Hardly Wait is a quintessential teen rom com you won't want to miss. It unfolds over the course of a raucous graduation night where various groups of students navigate love, friendship and self-discovery.

Release Date: June 12, 1998 | Watch Trailer

There's Something About Mary

There's Something About Mary movie poster
Photo: IMDb

Directed by the Farrelly brothers, this '90s rom-com follows the lovably awkward Ted (Ben Stiller) as he embarks on a journey to reconnect with his high school crush, Mary (Cameron Diaz). The catch? Well, let's just say an unfortunate zipper incident has left Ted with more than just emotional scars.

Release Date: July 15, 1998 | Watch Trailer

You've Got Mail

You've Got Mail movie poster
Photo: IMDb

Set against the backdrop of the early days of email and internet chat rooms, You've Got Mail tells the story of two people (played by Meg Ryan and Tom Hanks) who unknowingly fall in love online even though they're actually business rivals in real life.

Release Date: December 18, 1998 | Watch Trailer

10 Things I Hate About You

10 Things I Hate About You movie poster
Photo: IMDb

As one of the best '90s rom-coms out there, 10 Things I Hate About You is actually a modern adaptation of Shakespeare's The Taming of the Shrew. This teen classic is a stellar mix of humor, heart and high school drama, featuring a charismatic cast that includes Heath Ledger, Julia Stiles and Joseph Gordon-Levitt.

Release Date: March 31, 1999 | Watch Trailer

Never Been Kissed

Never Been Kissed movie poster
Photo: IMDb

In Never Been Kissed, Drew Barrymore shines as Josie Geller, a lovably quirky journalist assigned to go undercover in a high school. Her mission? To relive the teenage experience and, perhaps, finally earn her first real kiss.

Release Date: April 9, 1999 | Watch Trailer

Notting Hill

Notting Hill movie poster
Photo: IMDb

Starring Hugh Grant as a humble bookshop owner and Julia Roberts as a world-famous Hollywood actress, Notting Hill weaves a heartwarming tale of love and humor between two seemingly mismatched individuals.

Release Date: May 21, 1999 | Watch Trailer

Runaway Bride

Runaway Bride movie poster
Photo: IMDb

This 1999 romantic comedy reunites the charming on-screen duo of Julia Roberts and Richard Gere, following their iconic pairing in Pretty Woman. Roberts plays Maggie, a woman notorious for fleeing from the altar, while Gere is Ike, a New York journalist determined to write her story.

Release Date: July 30, 1999 | Watch Trailer

Drive Me Crazy

Drive Me Crazy movie poster
Photo: IMDb

Starring Melissa Joan Hart and Adrian Grenier, this romantic comedy follows the classic trope of friends turning into something more. As neighbors and childhood pals, their lives are far from exciting, until they hatch a plan to fake a relationship, shaking up their world in the process.

Release Date: October 1, 1999 | Watch Trailer

The Best Man

The Best Man movie poster
Photo: IMDb

Directed by Malcolm D. Lee, this dynamic and refreshing romantic dramedy delves into the lives of a group of friends reuniting for a wedding. Taye Diggs stars as Harper Stewart, a writer whose debut novel contains some closely-guarded secrets. When his book threatens to unravel relationships within the close-knit circle, tensions rise and friendships are put to the test.

Release Date: October 22, 1999 | Watch Trailer

She's All That

She's All That movie poster
Photo: IMDb

Starring Freddie Prinze Jr. and Rachael Leigh Cook, this '90s teen rom com revolves around a high school jock who takes on a bet to transform the school's "unpopular" girl into the prom queen. As the makeover unfolds, unexpected romances emerge.

Release Date: January 29, 1999 | Watch Trailer

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