11 Best Romantic Comedies From the 1990s

11 best romantic comedies from the 1990s

If the Oscars had a romantic-comedy category, these would’ve taken home the gold.

Sometimes the best cure for a stressful day or week is putting on a feel-good flick. And if you’re searching for one, the romantic comedies from the 1990s are a good place to start. After all, it was the heyday for rom-coms: Every weekend, it felt like there was a new box office hit, from Pretty Woman to She’s All That to The Best Man and beyond. There was no rest for rom-com aficionados.

And you can’t quite replicate the magic of the 90s rom-com genre (yes, it’s a genre in and of itself), as much as the film industry tries to with its remakes and replications. It just had a sparkle that no other decade has been able to match.

From Julia Roberts’ sensational performance in My Best Friend’s Wedding to Angela Bassett and Taye Diggs’ swirling romance in How Stella Got Her Groove Back, there are so many hilarious and heartwarming films to pick from. Even Netflix took a cue from the witty plots of the past and just released their take on a modern-day interpretation of She’s All That. It’s gender-swapped (yay!) and revolves around TikTok (boo!).

And with so many of this era’s fashion trends also coming back — from claw clips to Doc Martens and coordinating sets — we thought it would be fun to compile our favorite 90s rom-coms to give you a little wardrobe and love-life inspiration. Below, read our round-up of the best rom-coms from the 1990s. Trust us: It was hard to narrow down the list.

The Best 90s Romantic Comedies

My Best Friend’s Wedding (1997)

If you’re looking for 90s fashion inspo, every outfit Julianne Potter (played by Julia Roberts) wears in My Best Friend’s Wedding can be seen on today’s street style stars. Cropped tees with wide-leg pants, oversized men’s shirts layered underneath vests, and coordinating suits — she sports them all. This 90s rom-com classic starts when Big Red falls off her bed after her best guy friend (with whom she had “one hot month” in college) tells her he’s engaged and getting married to the rich daughter of the White Sox owner — played by a virginal Cameron Diaz. Roberts heads down a rabbit hole, trying to sabotage their wedding, and must come to terms with whether she actually loves her best friend, or if she’s just afraid of losing him. 

Reality Bites (1994)

When a group of Gen X friends graduates from college in Houston, they face the harsh reality most recent grads do: What’s next? Ben Stiller directs (and stars in) the flick, which chronicles a young cast of stars including Winona Ryder, Ethan Hawke, and Janeane Garofalo. Ryder’s character can’t seem to find a job (or figure out what she wants in life), so she starts filming a documentary about the trials and tribulations her friends are going through. Along the way, she realizes she might be falling for one of them. Naturally, he’s the one guy she always finds a reason to bicker with.

Love Jones (1997)

Before friends with benefits became a thing, there were situationships where two people straddled the line between full-on dating and just hooking up. Love Jones explores this in-between phase when a Chicago poet played by Larenz Tate, and a photographer, played by Nia Long, sleep together after their first date. Things get complicated as Long tries to figure out if he’s worth moving past her ex for, so she tests his love. Will he pass? 

She’s All That (1999)

Before you watch He’s All That, the remake Netflix just released that flips the gender dynamic of She’s All That, you have to watch the original. Nineties heartthrob Freddie Prinze Jr. stars as a popular high school jock (but, of course) who boasts that he can make Laney Boggs (an artsy loner played by Rachael Leigh Cook) prom queen within six weeks. Romance ensues. Backs are stabbed. And “Kiss Me” becomes a hit.

The Wedding Singer (1998)

Adam Sandler fans: If you miss his comedic days, you will definitely want to watch him struggle to hit notes as a 1980s-style wedding singer in this sweet-as-ever romantic comedy. Drew Barrymore plays a waitress who works at a reception hall where Sandler performs, and the two become friends after Sandler dives into an over-the-top depression after getting dumped by his fiancée at the altar. As Barrymore plans her own wedding, she leans on Sandler to help. Only, her relationship isn’t quite as made-for-each other as it seems. Buckle up and wait for one of the most epic displays of affection in airplane scene history.   

The Birdcage (1996)

If you’re looking for a beachside getaway without leaving the couch, this one’s for you. Miami’s South Beach sizzles as the backdrop of this hysterical film starring Robin Williams and Nathan Lane as drag club owners and longtime lovers. They must grapple with how to host their son’s super conservative future in-laws at their decadent apartment — and they make a lot of ridiculous decisions along the way.

How Stella Got Her Groove Back (1998)

If you’re itching to pencil in some vacation days, How Stella Got Her Groove Back is the one to watch. Angela Bassett plays Stella, an uber-successful stockbroker in San Francisco, who’s convinced by her bestie to travel to Montego Bay on a much-needed getaway. Against her own will, she goes, and she ends up meeting a dazzling local (played by Taye Diggs). The catch? He’s 20 years younger than her. This heartwarming rom-com will remind you that age really is just a number.

Sleepless in Seattle (1993)

Nora Ephron, who co-wrote and directed this heartfelt film, waves her magic wand across the story from beginning to end. An endearing Tom Hanks stars as a grieving widow whose 8-year-old son begs him to call into a national radio talk show to discuss his heartbreak. An engaged reporter, played by Meg Ryan, is among thousands of women who hear his story and is compelled to write him a letter, asking him to meet her on top of the Empire State Building on Valentine’s Day if he thinks they’ll be a good match. In a romantic twist of serendipitous events, the two romantics cross paths ahead of the holiday, but they don’t quite realize who each other is. You’ll be yearning for the two to connect through the very last scene. 

The Best Man (1999)

It’s one thing to write a book (selected by Oprah’s book club, nonetheless) about fictitious sexual romps. It’s another thing when you secretly include stories from your friends’ real-life encounters — and they get an advance copy of it right before your best friend’s wedding. All hell breaks loose on the wedding weekend, as the groom, played by Morris Chestnut, realizes that some of these sexual stories are about his future wife. Wild, unsuspecting, tragically romantic, and produced by Spike Lee, this is one you won’t want to skip.

10 Things I Hate About You (1999)

Set amid high school hallways in Seattle, this classic tale is a modern-day adaptation of Shakespeare’s The Taming of the Shrew. When an overbearing father declares his youngest daughter, Bianca, is only allowed to date if her older sister does, she goes into a fury, “But, daddy?!” The catch? Her older sister, played by Julia Stiles, is an angst-y feminist who wants nothing to do with immature teenage boys. So, Bianca and her friends lay out a plan to get her sister to fall in love. Enter: Heath Ledger, who plays a notorious bad boy paid to capture her heart.  

Practical Magic (1998)

Get in the mood for Halloween with this heartfelt movie about two witch sisters, played by Sandra Bullock and Nicole Kidman, who suffer from a tragic curse that causes any man they fall in love with to die. Kidman’s character gets married, anyway, and things don’t turn out well. So, the sisters reunite, and try to figure out how to release themselves from their doomed curse in order to find true love after all. Will they break free from the spell?