17 '90s Rom-Coms to Transport You to a Simpler Time
When life feels like too much, these familiar favourites are the best reset.
Desperate for some mental respite? A surefire way to facilitate momentary suspension of disbelief is to experience the fantastical worlds of 1990s romantic comedies, where New York City apartments are impossibly huge, and every male romantic prospect is either Tom Hanks or Bill Pullman. (You are Meg Ryan, always.) The mid-’90s is a real sweet spot for the genre, punctuated by the flagship films of Nora Ephron and filled with more underrated gems that you forgot even existed.
Need we say more? Get cosy under the covers and press play on one of these '90s rom-coms.
Sleepless in Seattle (1993)
Where can I watch it? Binge
Yes, When Harry Met Sally made Meg Ryan an icon, but Sleepless in Seattle gave us her and Tom Hanks as the ultimate rom-com couple whose chemistry is simply unparalleled – and they only share two minutes of screen time. That's magic. Directed by the late, great Nora Ephron, Sleepless in Seattle is peak Meg Ryan, peak '90s, and the cast is truly wonderful: Hanks' real-life wife Rita Wilson plays his sister, Victor Garber plays Ryan’s fiancé’s father, Bill Pullman is Ryan's fiancé, and Gaby Hoffmann plays a friend of Hanks’ son. Set between New York and Seattle, this one is best streamed on a rainy day under the covers.
While You Were Sleeping (1995)
Where can I watch it? Disney+
Only Sandra Bullock could make this premise seem whimsical and not highly problematic. In While You Were Sleeping she plays Lucy, a ticket booth operator who develops a crush on one of the regular passengers – a handsome stranger played by Peter Gallagher (aka Sandy Cohen from The O.C.) One day she saves his life and when he ends up in a coma the hospital mistakenly identifies her as his fiancée. She rolls with it and pretends to be the wife-to-be of this random guy, with no end game in sight. Enter Bill Pullman – the ultimate unassuming nice guy of '90s rom-coms – Gallagher’s younger brother, who starts getting suspicious. Romantic vibes aplenty follow.
Love Jones
Where can I watch it? Apple TV and Prime Video ($4.99)
A true cult classic, Love Jones is a romantic drama about two young creatives in Chicago navigating attraction, timing, ego, and emotional readiness. Larenz Tate plays Darius Lovehall, a poet, and Nia Long plays Nina Mosley, a photographer. Miscommunication, pride, and exes (relatable!) get in the way, and the film tracks their on-again, off-again dynamic. If you love a sensual, vibe-driven film that’s heavy on atmosphere and light on melodrama, this one’s for you.
It Could Happen to You (1994)
Where can I watch it? YouTube
An underrated gem inspired by a true story, this one stars Nicolas Cage and Bridget Fonda. Cage plays an NYC cop who wins the lottery and splits the money with a waitress played by Fonda. With Rosie Perez and Stanley Tucci in supporting roles, It Could Happen to You will satisfy your '90s rom-com cravings and then some.
Poetic Justice (1993)
Where can I watch it? Apple TV
Janet Jackson and Tupac Shakur? It doesn’t get any more ’90s than that. Jackson plays an aspiring poet processing her trauma, while the late Shakur, in his big-screen debut, plays Lucky, a postal worker with his own demons. They embark on a road trip where grief, love, and emotional healing are explored through conversation and poetry. It’s largely dialogue-driven, focusing on the chemistry between the leads. The film carries far more poignance and cultural weight than most rom-coms, a perfect option if you’re in the mood for a heartfelt tear-jerker.
The Bodyguard (1992)
Where can I watch it? Prime Video
“And I… will always love you.” Be honest, you can hear Whitney Houston’s voice in your head. Although it’s often overshadowed by its iconic theme song, the film itself is glossy ’90s melodrama at its best. Houston plays Rachel Marron, a wildly successful singer and actress who begins receiving increasingly disturbing threats. Enter Frank Farmer (Kevin Costner), an ex–Secret Service agent brought in to overhaul her security. Their personalities clash immediately, but as the threats escalate, their mutual distrust slowly shifts into attraction, culminating in a dramatic and moving conclusion.
You've Got Mail (1998)
Where can I watch it? Prime ($4.99)
Reunited (and it feels so good), Meg Ryan and Tom Hanks team up for another Nora Ephron-directed romantic comedy of errors that will make you nostalgic for dial-up modems and internet anonymity. Supporting the leads are Dave Chappelle, Greg Kinnear, Parker Posey, and Heather Burns (Miss Congeniality's Miss Rhode Island, whose idea of the perfect date is April 25th because it's not too hot, not too cold – all you need is a light jacket). "That caviar is a garnish!" "Don't you love New York in the Fall? It makes me wanna buy school supplies." "F-O-X." If you know, you know. And if you don't – treat yourself to this forever classic, now.
Muriel's Wedding (1994)
Where can I watch it? Stan
This '90s classic can be considered a tragedy as much as a comedy depending on who you ask, but however you view it, it's a culturally significant artefact from the golden age of Australian cinema (see also: Strictly Ballroom; Priscilla, Queen of the Desert). It's the story of a single, socially awkward woman who dreams of having a bigger life in the big smoke and a spectacular wedding to a handsome fella. The music of ABBA features prominently, preceding the Mamma Mia musical (which debuted in 1999), and you will be singing Waterloo for weeks after viewing.
Clueless (1995)
Where can I watch it? Stan
Another icon of cinema history, Amy Heckerling's adaptation of Jane Austen's Emma is an enduring favourite. No recap needed. On your next rewatch, take a moment to appreciate Cher's debate class monologue on the refugee crisis that remains relevant today, and remember that it absolutely does not say "RSVP" on the Statue of Liberty. Also, long live Brittany Murphy.
Boomerang (1992)
Where can I watch it? Apple TV
Before millennials came to know him as the voice of Donkey in Shrek or Mushu in Mulan, Eddie Murphy was already one of the biggest stars in Hollywood. In Boomerang, he plays Marcus Graham, a smooth-talking marketing hotshot. While slick and charming, the way he treats his romantic interests leaves much to be desired. After seeing his shortcomings reflected in his ambitious new boss, Jacqueline (Robin Givens), he’s forced to confront his own selfishness and consider what a healthy relationship might look like, with the one and only Halle Berry no less. Look, this was made over 30 years ago, so like many of the films on this list, some of the jokes haven’t aged well. But if you view it for what it was, you’ll still have a lot of fun.
Notting Hill (1999)
Where can I watch it? Disney+
What happens when the most famous movie star in the world walks into a quiet London bookshop? One of the most iconic romantic comedies on film. In Notting Hill, directed by Roger Mitchell, Anna Scott (Julia Roberts) falls for endearingly awkward bookseller William Thacker (Hugh Grant), sparking a romance that feels both impossible and deeply ordinary. It’s tender, funny, and home to one of the most iconic rom-com lines of all time: “I’m just a girl, standing in front of a boy…” A tried-and-true favourite.
French Kiss (1995)
Where can I watch it? Apple TV+
Meg Ryan doing what Meg Ryan does best – falling in love somewhere picturesque. When Kate flies to France to win back her fiancé, she instead meets a charming (and slightly shady) Frenchman played by Kevin Kline. What unfolds is a slow-burn enemies-to-lovers story set against vineyards, train rides, and sun-drenched countryside. It’s the exact right amount of escapist and witty, and perfect on the rewatch, every time.
The Wedding Singer (1998)
Where can I watch it? HBO Max
Set in the ’80s but released at the height of the ’90s rom-com era, The Wedding Singer follows Robbie (Adam Sandler), a hopeless romantic wedding performer nursing a broken heart, and Julia (Drew Barrymore), a waitress engaged to the wrong man. It’s nostalgic and funny and cringe and surprisingly heartfelt – a reminder that grand romantic gestures (especially the airborne kind) never go out of style. Dare we say Sandler at his best?
Waiting To Exhale (1995)
Where can I watch it? Disney+
Waiting to Exhale follows four longtime friends: Whitney Houston as Savannah, a successful TV producer involved with a married man; Angela Bassett as Bernadine, whose husband leaves her for a younger woman; Lela Rochon as Robin, a high-earning executive stuck in a string of unfulfilling relationships; and Loretta Devine as Gloria, a single mother tentatively re-entering the dating world. Themes of divorce and reinvention, desirability, and the messy reality of love elevate this warm film beyond standard romantic drama. Above all, this is a film about solidarity and support, where friendship becomes the real love story.
10 Things I Hate About You (1999)
Where can I watch it? Stan
A modern retelling of Shakespeare’s The Taming of the Shrew, this late-’90s classic gave us brooding bad boys and a poem scene that still cuts in the best way. Kat (Julia Stiles) and Patrick (Heath Ledger) deliver one of the best teen romances ever put to screen (no bias here, we swear), dripping with sarcastic banter and genuine vulnerability. Bonus points for the unforgettable stadium serenade.
How Stella Got Her Groove Back (1998)
Where can I watch it? YouTube, Google Play and Apple TV ($11.99)
Woefully underrated, How Stella Got Her Groove Back is a romantic drama about burnout and the pressures faced by ambitious women. Angela Bassett plays Stella Payne, a 40-year-old, ultra-successful stockbroker and single mother who hasn’t taken a real break in years. At the urging of her best friend (played by Whoopi Goldberg), she takes a trip to Jamaica, where she meets Winston (Taye Diggs), a charming, much younger medical student. Stella confronts questions about age, respectability, vulnerability, and whether she’s allowed to choose joy over responsibility – all on the backdrop of a tropical beach.
Four Weddings and a Funeral (1994)
Where can I watch it? Stan
Before Hugh Grant (of the aforementioned Notting Hill fame) became the blueprint for charmingly flustered, floppy-haired British men everywhere, there was Four Weddings and a Funeral. The film follows his protagonist Charles and a tight-knit, off-kilter group of friends navigating love and loss and connection and the unpredictability of timing. A classic for a reason, it balances laugh-out-loud moments with genuine heartbreak. A specific shoutout to Kristin Scott Thomas – no reason other than she’s incredible in everything she does.
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