10 Most Rewatchable 90s Rom-Coms, Ranked

Quite possibly the golden era of romantic comedies, the 90s left viewers swooning for epic love stories. This decade produced rom-com icons and couples that audiences still ship for today, a feat that has yet to be replicated successfully since. Sure, these features set unrealistic expectations for high school romances, will-they-won’t-they, and the all too dreamy “take me back, I love you” at the end just before the credits roll. However, that is what makes them so beloved and rewatchable.

These zany demonstrations and professions of love may not exist in the real world, but by doing so, they fulfill the purpose of escaping to the movies. Not just for watching around Valentine’s Day or the holidays, the best 90s rom-coms are rewatchable for any occasion. Thanks to iconic lines and scene-stealing moments, audiences return to these movies for the satisfaction of reliving a love story, no matter the level of cheesiness, cringe, or detachment from reality.

10 ‘Never Been Kissed’ (1999)

Director: Raja Gosnell

Drew Barrymore stars as junior reporter Josie Geller as she poses as a high school student in order to write an article on teenage culture. There, she unexpectedly falls for her English teacher, Sam Coulson (Michael Vartan), throwing a wrench into her research. Never Been Kissed features a supporting cast including David Arquette, Molly Shannon, and John C. Reilly.

Part of the fun of rewatching Never Been Kissed is existing in a world where this plot seems like a good idea or entirely plausible. It’s the romance that many viewers wished they’d experienced in high school, and Barrymore’s Josie gets a do-over to find it. To this day, audiences find a sweetness in Barrymore’s performance that overrides the this would never happen energy movies of this genre provide. The film is charming and winning and marked the last “hurrah” for a decade that changed the way audiences look at the rom-com genre.

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9 ‘She’s All That’ (1999)

Director: Robert Iscove

It is not the greatest high school love story ever told, and as it ages, it definitely falls into the shallow pool. However, decades later, She’s All That still maintains its status as a genre favorite. Freddie Prinze Jr. is the all-popular Zack Siler who, after being dumped by his queen bee girlfriend, takes a bet to transform introverted outcast Laney Boggs (Rachael Leigh Cook) into the next prom queen.

She’s All That is an ugly duckling story that is on the outskirts of feeling like a John Hughes film. It’s become synonymous with 90s romantic comedy for its character archetypes that genre movies of today replicate. Not only do audiences return to watch for its charismatic leads but also its supporting cast, including Paul Walker, Matthew Lillard, Usher, Jodi Lyn O’Keefe, Anna Paquin, and Kieran Culkin. It’s worth the trip down memory lane for its cast alone.

She’s All That

Release Date

January 29, 1999

Cast

Freddie Prinze Jr. , Rachael Leigh Cook , matthew lillard , Paul Walker , Jodi Lyn O’Keefe , Kevin Pollak

Runtime

95

Watch on Paramount+

8 ‘There’s Something About Mary’ (1998)

Directors: Bobby Farrelly, Peter Farrelly

This feature is the notable 90s installment in the one-that-got-away category. Mary (Cameron Diaz) is the prom date who dramatically never happened for Ted (Ben Stiller) after a freak accident. Thirteen years later and still crushing on Mary, Ted attempts to reconnect with her by hiring Pat (Matt Dillon) to find and gather intel on her. Alas, Pat has other motives as he tries to trick Mary into dating him.

There’s Something About Mary is stupid funny, brought to the screen by the directors of Dumb and Dumber. The movie is heavily rooted in puerile-style comedy, using a love story as a driving justification but featuring plenty of the crass, gross-out humor that characterized the Farrelly Brothers‘ early career. An R-rated comedy, it was a hit with critics and audiences that catered to a variety of viewers in one sitting. Today, There’s Something About Mary remains unique as the rare rom-com that is as hilarious as it’s romantic.

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7 ‘The Wedding Singer’ (1998)

Director: Frank Coraci

With a recipe made in rom-com heaven, The Wedding Singer remains one of Adam Sandler‘s best. He stars as Robbie Hart, who, despite a broken engagement, continues his job as a wedding singer. Everything changes when he meets Julie (Drew Barrymore), and he falls hard for her. The only problem? She’s engaged to another man, forcing Robbie to embark on a mission to break them up and confess his feelings before it’s too late.

Broken hearts, wrongful engagements, and a lot of wedding song covers make for the perfect backdrop in a 90s rom-com. The Wedding Singer is one of the first times when Sandler stepped out of his usual lane to deliver a comedy that’s as heartwarming as it is funny. Sandler and Barrymore’s chemistry here is unmatched, and Exhibit A for why they continue to pair well in this genre. Heartwarming and funny, The Wedding Singer is a gem of a rom-com and a highlight of Sandler and Barrymore’s careers.

The Wedding Singer

Release Date

February 13, 1998

Cast

Adam Sandler , Drew Barrymore , Christine Taylor , Allen Covert , Matthew Glave , Ellen Albertini Dow

Runtime

95

Rent on Apple

6 ‘You’ve Got Mail’ (1998)

Director: Nora Ephron

Directed by the behind-the-camera rom-com queen Nora Ephron, You’ve Got Mail is a 90s-defining romantic comedy. It features two of the generation’s biggest stars, Meg Ryan and Tom Hanks, as they break the golden rule in romance: don’t fall for the enemy. A bookshop owner, Kathleen (Ryan), unknowingly engages in an internet romance with a man she hates, Joe (Hanks), the man who happens to be trying to run her out of business.

You’ve Got Mail is incredibly rewatchable for the online dating portion alone. The charming chemistry between Hanks and Ryan is addicting as they battle wits and feelings, culminating in one of the best love confessions ever. You’ve Got Mail is a delightful and cozy throwback to a simpler time before dating apps and social media. It’s the rom-com equivalent to comfort food, a film that’s so entertaining and sweet that viewers can’t help themselves from revisiting it often.

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5 ‘Clueless’ (1995)

Director: Amy Heckerling

Whether it’s inspiration for Halloween costumes or because it’s one of those must-see films, Clueless remains a top contender in every 90s rewatchable conversation. The It-Girl of her Beverly Hills high school, Cher (Alicia Silverstone), prides herself on her matchmaking skills after successfully pairing up two of her teachers. She takes on a new endeavor of giving the new girl, Tai (Brittany Murphy), a makeover, only to have it backfire on her and threaten her social status.

Clueless pokes fun at the absurdity of teenage melodrama and the mentality of a Beverly Hills high school. An adaptation of Jane Austen’s Emma, the 90s soft satirical take is easily digestible decades later. In true rom-com fashion, it’s the story of a girl obsessed with everything of material importance instead of what actually matters. Funny, witty, and endlessly quotable, Clueless is a milestone of 90s cinema, a generation-defining teen rom-com that stands the test of time even under the heavily scrutinizing modern eye.

Clueless

Release Date

July 19, 1995

Runtime

97

Watch on Paramount+

4 ’10 Things I Hate About You’ (1999)

Director: Gil Junger

The stellar performances by Heath Ledger and Julia Stiles are the reasons 10 Things I Hate About You remains a go-to for rom-com fans. The high-school bad boy, Patrick (Ledger), is tasked with dating the class know-it-all, Kat (Stiles), as a means for Kat’s younger sister Bianca (Larisa Oleynik) to have a social life. Not the odd couple they appear to be, Kat and Patrick find they have more in common as what started as a paying job for Patrick turns into something more.

Audiences return to this movie time and time again for two reasons: to see Heath Ledger grace the screen again, a beloved actor gone too soon, and for Stiles’ famous delivery of Kat’s class poem in which she confesses her feelings for him. 10 Things I Hate About You is a romantic comedy that fans do not want remade or sequels produced, rather to rewatch it any time the nostalgia for 90s romance strikes. It’s a film that will never go out of style—not even a little bit, not even at all.

10 Things I Hate About You

Release Date

March 31, 1999

Runtime

97

Watch on Disney+

3 ‘Notting Hill’ (1999)

Director: Roger Michell

William Thacker (Hugh Grant) is a bookstore owner whose personal and romantic life is thrown for a loop when he meets famous actress Anna Scott (Julia Roberts). While their romance blossoms, turmoil ensues as the paparazzi’s obsession with Anna complicates their relationship, forcing them to confront their radically different lifestyles.

There’s no substitution for masterful romantic chemistry, which is why Notting Hill is not only one of the most rewatchable 90s rom-coms but one of the best rom-coms ever. Roberts and Grant are magic in this BAFTA-winning flick. Grant is a household name in rom-com and British cinema, while Roberts is rom-com royalty, arguably cinema’s greatest leading lady in the genre. With a charming script, this opposite-world romance gives audiences a sense of hope and escapism that few modern rom-coms have.

Notting Hill

Release Date

May 28, 1999

Runtime

124 minutes

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2 ‘Sleepless in Seattle’ (1993)

Director: Nora Ephron

After losing his mother, Jonah (Ross Malinger) calls into a Seattle radio show to find a wife for his widowed father, Sam (Hanks), who reluctantly discusses his feelings on-air. Upon hearing the broadcast, Baltimore reporter Annie (Ryan) finds an instant connection with Sam even though she’s engaged. The potential of their romance culminates in an invitation sent by Annie to Sam for him to meet her at the Empire State Building on Valentine’s Day.

Oscar-nominated and the second major outing for Tom Hanks and Meg Ryan with Nora Ephron, Sleepless in Seattle calls out to the long-distance romantics and their desire for epic meetings. It’s the perfect will-they-won’t-they-end-up-together scenario across the miles as Sam and Annie don’t share the screen until the final act. The most epic meet-cute of the 90s, Sleepless in Seattle expertly balances romance and comedy, not sacrificing story progression for one or the other. With the success of their chemistry in Joe Versus the Volcano and You’ve Got Mail, Hanks and Ryan prove once again they can lead a swoon-worthy rom-com.

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1 ‘Pretty Woman’ (1990)

Director: Garry Marshall

From its quotable exchanges to that show-stopping red dress, Pretty Woman is the most rewatchable rom-com of the decade—and maybe in the genre as a whole. Genre royalty Julia Roberts stars as Vivian, an L.A. prostitute who accompanies the wealthy Edward (Richard Gere) for the weekend as he stays for a business trip. What was supposed to be a limited engagement turns into a full-blown romance as a Cinderella story unfolds for the two unlikely lovers.

This is undeniably the best installment in Roberts and Gere’s working relationship. Roberts is mesmerizing, always with a mile-wide smile and her iconic red hair, as Vivian stumbles through adjusting to Edward’s proper and cutthroat world. Audiences are well aware that love doesn’t happen like this in the real world, making it an escapism movie for rom-com lovers. And who doesn’t love rewatching that redemption scene on Rodeo Drive? Pretty Woman is the ultimate romantic comedy, respecting the genre’s rules while still including enough refreshing updates to make it enchanting and outright addictive.

Pretty Woman

Release Date

March 23, 1990

Runtime

119

Watch on Hulu

NEXT: 15 Most Rewatchable Modern Rom-Coms, Ranked