10 Iconic Rom-Coms From the ’90s That Everyone Should Watch

Wintertime always makes us feel extra cozy and nostalgic, and few eras have a choke hold on us quite like the 1990s.

Whether you were there or not, there's something irresistible and lasting about the best '90s styles, music and, of course, movies—and romantic comedies in particular. Whether or not they've aged perfectly well, they capture a spirit, telling stories that make us laugh out loud as our hearts soar. There are so many classic rom-coms from the time that everyone should see at least once, and below, we've collected 10 of the very best.

(10 Things I Hate About You via Buena Vista Pictures Distribution)

Four Weddings and a Funeral (1994)

Sometimes, the best romances unfold over time and by chance, and we can't get enough of the slow burn of Mike Newell's Four Weddings and a Funeral. The Academy Award-nominated film stars Hugh Grant as Charles, following him and his friends through five social events—the titular weddings and a funeral—and his chance encounters with Carrie, played by Andi MacDowell. After striking up a romance, they part ways and go on with their lives (with two of the aforementioned weddings being their marriages to other people), leaving viewers wondering what might happen next and if they'll ever finally be together.

 

Shakespeare in Love (1998)

Prepare to see Shakespeare mentioned a lot on this list, starting with 1998's Shakespeare in Love. It stars Joseph Fiennes as the famous William Shakespeare in the middle of a bout of writer's block. Meanwhile, a woman named Viola (Gwyneth Paltrow) has begun disguising herself as a man in order to act in Shakespeare's plays, as it's forbidden for women to do so. He's inspired by her performance, allowing him to write Romeo & Juliet. Once he discovers her true identity, they begin a romance. It's doomed from the start, as she's betrothed to a greedy lord, but the love they share goes on to inspire his greatest plays.

 

How Stella Got Her Groove Back (1998)

We can think of few things better than Angela Bassett as the star of a rom-com, making How Stella Got Her Groove Back is truly iconic. It follows the titular Stella, a 40-year-old single mom who's been very successful in her career, but not in love. Everyone wonders when she's going to start dating again, so she decides to send her son to live with his dad for two weeks and books a ticket to Jamaica, where she meets Winston, a handsome and captivating local. The only problem is that he's half her age. They almost strike up a romance, though fate intervenes, and when she quickly loses her job and best friend in quick succession while contemplating the potential relationship, she's forced to figure out her priorities.

 

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My Best Friend's Wedding (1997)

We can never pass up a rom-com that plays with our expectations, and that's exactly what you'll get from My Best Friend's Wedding. It stars Julia Roberts and Dermot Mulroney as best friends who've made a pact to marry each other if they're still single at age 28. Less than a month before her 28th birthday, she receives news that he's engaged, quickly realizing she's in love with him and going to extreme lengths to sabotage the new relationship. Truly, this is one of the greatest Julia Roberts performances of all time.

 

10 Things I Hate About You (1999)

10 Things I Hate About You is a modernization of William Shakespeare's The Taming of the Shrew, reminding us just how timeless and romantic his plays can be. It follows a popular teenage girl, Bianca, whose dad forbids her to start dating until her rebellious and antisocial older sister, Kat, does the same. Bianca makes it her mission to get mysterious bad boy, Patrick, to woo Kat. Soon, Bianca finds that getting what she wanted is bittersweet, and Kat is surprised by the feelings she develops, before being heartbroken to find out about her sister's scheme.

 

The Parent Trap (1998)

You might not immediately think of Lindsay Lohan's 1998 masterpiece The Parent Trap as a romantic comedy, but at the end of the day, the film's all about bringing the parents back together. This remake stars Lindsay in dual roles as twins Annie and Hallie, whose parents separated shortly after their birth, living on different continents. They have to idea about each other until a fate encounter at a summer camp reunites them, inspiring them to come up with the ultimate plan to get their mom and dad to fall in love again and bring the whole family back together.

 

Much Ado About Nothing (1993)

No matter how many times Shakepeare's Much Ado About Nothing gets remade, it never loses its charm, and Kenneth Branagh's 1993 adaptation will continue to stand the test of time. Featuring big names including the director himself, plus Emma Thompson, Denzel Washington, Michael Keaton, Keanu Reeves and more, it follows the budding romances between Claudio and Hero, as well as Benedick and Beatrice, with the villainous Don John attempting to sabotage them, and misunderstandings and confusion looking to undo them at every turn.

 

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Chasing Amy (1997)

We'll start this off by saying that Chasing Amy's approach to queer issues doesn't quite gel in the modern day, but the clever, funny writing and thoughtfulness still make it worth watching. It starts Ben Affleck as Holden, a comic book artist who falls for Alyssa, played by Joey Lauren Adams. The problem is, she's a lesbian, and as they spend more time together, Holden's work and relationship with his best friend suffer. Eventually, Holden and Alyssa do begin a relationship, but insecurity soon gets in the way, with his efforts to fix things driving an even bigger wedge between them.

 

Clueless (1995)

Clueless is another unexpected adaptation, loosely based on Jane Austen's Emma. It follows popular high school student Cher, who gets hooked on performing good deeds after setting up two of her teachers helps her get a good grade in her toughest class. She sets her sights on "clueless" new student Tai, deciding to give her a makeover and a confidence boost and setting her up with one of the most popular boys in school. Things don't go exactly according to plan, and in the process, Cher realizes she's equally unaware when it comes to matters of love. We will say the romance that develops is a bit iffy, but also cute? The '90s were a weird time.

 

Sleepless in Seattle (1993)

And finally, this list wouldn't be complete without a film by Nora Ephron, the queen of romantic comedies. She directed Sleepless in Seattle, a unique romance that sees its two leads, played by Tom Hanks and Meg Ryan, not meet until the end of the film. He plays a widower named Sam whose 8-year-old son calls into a radio program, urging his dad to share his story about his grief over his wife's death. His story becomes a hit with women around the country moved by his vulnerability. Among them is a reporter named Annie (Meg Ryan), who's engaged, but unsatisfied in her relationship. Annie writes Sam a letter, declaring they should meet on the Empire State Building on Valentine's Day. She decides not to send it, but her editor does anyhow. Despite Sam's hesitation, and his new relationship, he agrees to the meeting, leaving the rest of up to fate.

 

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