Few eras can match the energy of the 90s when it comes to movie diversity. Independent films saw a level of distribution previously unheard of, and kickass women’s stories from the 80s expanded into more range for women’s roles in the 90s. I know I’m extremely biased as a child of the era, but the films of the 90s allowed a real explosion in watchable, tender, funny, fun filmmaking! In addition to 90s rom coms, I’ve compiled a list that includes some of my favorite comfort movies from the decade.
For other comfort movies from the era, check out my list of 80s rom coms!
90s Rom Coms
HouseSitter (1992)
Despite being two of my favorite comedic actors of the era, I had NO clue Goldie Hawn and Steve Martin starred together until someone recommended this movie to me! I love that even when he’s playing the “straight man,” Steve Martin’s silliness can’t help but come out.
Fun Fact: The Taiwanese name for the film translates to, “Half a Wife in My Soup.”
Synopsis: After a one-night stand, an ambitious con woman makes herself at home in straight-edge Newton’s new house.
Dave (1993)
This is technically the first movie I ever saw, as my parents took my twin sister and I when we were approximately six weeks old. My mom remembers this movie fondly, because she was holding me and I slept the whole time. That may have increased my love for it, but it’s still a little jewel of a movie nonetheless.
Fun Fact: The driving scenes were shot in such a way as to actually follow the layout of Washington, D.C.
Synopsis: An ordinary man named Dave is called in by the secret service when it’s discovered he’s a dead ringer for the out-of-commission president.
Groundhog Day (1993)
I am hard-pressed to think of a more universally beloved film than Groundhog Day. It has everything – comedy, romance, goofiness, big hair, deep existential questions. Andie MacDowell is far too hot for Bill Murray, but that’s little matter in Hollywood.
Fun Fact: The groundhog bit Bill Murray, twice.
Synopsis: A real d-bag of a weatherman is trapped in a time loop in Punxsutawney, Pennsylvania on Groundhog Day and uses it as a chance to woo a woman.
Four Weddings and a Funeral (1994)
Another stop on the Andie MacDowell fan club tour, Four Weddings and a Funeral is for the quintessential anglophile. It’s deeply charming and very beautiful and has one of the saddest scenes in all of cinema.
Fun Fact: Filmed in just over a month due to its low budget.
Synopsis: A bumbling British man falls in love with a beautiful American woman after multiple serendipitous meetings.
It Could Happen to You (1994)
The 90s saw a lot of relatable working-class content like no other era before or since. Rather than parodying or poking at middle America, this cute rom com lives in a deeply relatable era (and the height of the American middle class).
Fun Fact: Based on a true story (although the real life cop and server did not get together).
Synopsis: When a cop doesn’t have enough for a tip at a diner, he promises the server he’ll split his lotto ticket with her – if it’s a winner. Much to everyone’s surprise, including his wife, he wins $4 million.
Clueless (1995)
I knew this movie was good, but I didn’t realize it was great until I went to see it in theaters at the local Alamo Drafthouse for a special re-release. The dialogue snaps and whizzes, the fashion bursts off the screen, and the whole thing reeks of 90s charm. Alicia Silverstone transforms my least favorite Jane Austin heroine into someone of elite charm.
Fun Fact: In a moment of life imitating art, much of the slang in the movie was written for the film, and seeped into pop culture from there.
Synopsis: A pampered Beverly Hills princess learns just how Clueless she is when she tries to transform the new girl in school.
The Preacher’s Wife (1996)
Sometimes infidelity is extremely charming! It helps when the chemistry is too good to ignore – as with Whitney and Denzel. Based on a 1947 movie called “The Bishop’s Wife,” the 90s version is way more sizzling and so, so lovable.
Fun Fact: The director removed an extra wearing a yellow sweater in a church scene, because it was too close to the yellow choir robes. That extra was Melissa McCarthy.
Synopsis: With his church and his marriage in trouble, Rev. Henry Biggs calls on God to help him. God sends a super handsome angel, who’s taken with the preacher’s wife.
Rodgers & Hammerstein’s Cinderella (1997)
It’s hard to believe the late 90s gave us two fabulous Cinderella retellings! In this adaptation of the Rodgers and Hammerstein musical, 90s powerhouses like Brandy, Whitney Houston, Bernadette Peters, Jason Alexander, and Whoopi Goldberg tell the classic tale with an undeniable wealth of charisma.
Fun Fact: The best-selling video of a made-for-TV movie (with record-breaking ratings).
Synopsis: A beautiful orphan gains the attention of a handsome prince with the help of a benevolent fairy godmother.
Ever After (1998)
Less magical, but more bewitching than the original source material! Set in 16th-century France, this Cinderella is plucky, resourceful, and wears one of the best gowns to ever grace our screens.
Fun Fact: The stroke Drew Barrymore uses as she swims in the lake was in fact a popular swimming stroke during the era.
Synopsis: Fleeing an arranged marriage, a prince meets an enchanting young woman in the forest. Posing as a noblewoman, Danielle meets the prince again at a ball, much to her domineering stepmother’s chagrin.
How Stella Got Her Groove Back (1998)
This movie is perhaps even more relevant today, as the protagonist’s plight (over 40 and over worked) applies to even more women now. It’s a really fun rom com, but at its heart, this movie is about friendship and finding yourself.
Fun Fact: Taye Diggs was starring as Benny in Rent on Broadway when he was cast for this movie.
Synopsis: When her wacky friend Delilah convinces her to go on a Jamaican vacation, beautiful, successful Stella meets a handsome younger man.
The Parent Trap (1998)
This movie could not be more important to millions of women brought up in this era. With a fantastic soundtrack and an iconic performance from a young Lindsay Lohan, this movie – dare I say – eclipses the original.
Fun Fact: Lindsay Lohan insisted on many of the differentiating characteristics between the twins, including Hallie’s blue hard candy nail polish (which had to be constantly taken off and re-applied as she switched between characters).
Synopsis: After discovering each other at summer camp, twins separated at birth conspire to get their parents back together.
The Wedding Singer (1998)
With her sunny face and infectious smile, Drew Barrymore anchored many off-beat rom coms in this era. Up against a young Adam Sandler for the first time, this offbeat, hilarious movie shows both actors off to the fullest.
Fun Fact: Lots of famous writers beefed up the script behind the scenes – including Carrie Fisher and Judd Apatow.
Synopsis: A wedding singer and a cocktail waitress who’ve worked many weddings together prepare to wed other people – and slowly realize their mistake.
You’ve Got Mail (1998)
Listen, there are some deeply problematic elements of this movie, chief among them the fact that Tom Hanks lies to Meg Ryan’s character for a long time before coming clean. But as a celebration of the Upper West Side, and a nostalgia boost for children’s literature, it works beautifully.
Fun Fact: Meg Ryan bought her first computer while filming the movie.
Synopsis: A children’s bookstore owner starts an anonymous romance via AOL with a man who turns out to be the son of the bookstore tycoon who put her out of business.
Runaway Bride (1999)
I could’ve put any number of Julia Roberts films of this era on this list, but truthfully, I believe this movie to be criminally underrated. Roberts and Richard Gere have incredible chemistry, and the ultimate message of the film? Authenticity is the key to a healthy relationship.
Fun Fact: Julia Roberts only agreed to appear in this movie on the condition that it not be written as a sequel to Pretty Woman.
Synopsis: After being fired from his columnist job for writing a semi-libelous article about her, New York hotshot Ike Graham travels to Hale, Maryland to get the scoop on the “Runaway Bride.”
90s Comedies
Mermaids (1990)
My feelings about this movie grow more complicated and deep every time I watch it. A coming-of-age story, you can watch it at nearly any age and find something deeply relatable. Plus, Winona Ryder is just so great at playing a weirdo.
Fun Fact: Cher’s cover of “The Shoop Shoop Song (It’s in His Kiss)” recorded for the film reached #1 in the UK.
Synopsis: A beautiful single mother settles in 1960s Massachusetts with her daughters, a deeply religious teen and a quirky 9-year-old.
City Slickers (1991)
Raised on a horse farm, my sisters and I took endless delight from this fish-out-of-water comedy as kids. Beneath all of the antics, however, there’s a pretty powerful lesson about connecting to nature and finding your way.
Fun Fact: Daniel Stern declined the studio’s offer of horseback riding lessons in order to make his on-camera inexperience authentic.
Synopsis: Three middle-aged Manhattanites decide a cattle drive from New Mexico to Colorado holds the key to the best way to deal with their respective mid-life crises.
Father of the Bride (1991)
Despite centering around a wedding, this movie serves more to examine the phases of life. I am positive my deep, abiding love for Steve Martin, Martin Short, and ESPECIALLY Diane Keaton started with this film. The house in this movie reigns supreme as the ultimate Nancy Meyers house. (Though Baby Boom still has my favorite kitchen).
Fun Fact: Brad Paisley fell in love at first sight with Kimberly Williams (Annie) when he saw the movie in theaters. They have been married since 2003.
Synopsis: A deeply caring and somewhat erratic father struggles with letting go for his daughter’s wedding.
My Cousin Vinny (1992)
This movie is worth watching for Marisa Tomei’s Oscar-winning monologue alone. It’s one of my favorite movies to throw on when I need some levity. It’s rated R because there are a few extra F bombs, but you can safely watch it with any kid who can handle a PG-13 movie.
Fun Fact: Thanks to the accuracy of courtroom procedure and pretrial hearings, this movie often gets taught in law classrooms.
Synopsis: A Brooklyn tough guy-turned-lawyer gets the assignment of his life when his younger cousin is arrested for murder in rural Alabama.
Sister Act (1992)
If my formerly Catholic mother ever thought twice about my constant singing of “Salve Regina,” she never showed it. Despite the many, many silly jokes, it’s such a tender look at the power of community, and an exploration of what community REALLY means.
Fun Fact: Kathy Najimy and Wendy Makkena pranked their hotel by order room service while still in their nun’s habits and turning on porn when the porter showed up with their food.
Synopsis: A Reno lounge singer goes into witness protection at a struggling San Francisco convent after witnessing her mafioso boyfriend murder someone.
Mrs. Doubtfire (1993)
When your kids ask, “who was Robin Williams?” Show them this movie. Endlessly quotable, endlessly ridiculous, endlessly parody-able. I loved it as a kid and I love it even more with every year that goes by.
Fun Fact: In the original ending, the parents get back together, but both Robin Williams and Sally Field rallied to give the film a healthier, more realistic ending.
Synopsis: After a brutal divorce, a down-on-his-luck actor poses as an elderly British nanny to spend more time with his children.
Muriel’s Wedding (1994)
Starring a very young Toni Collette as the lovable, slightly-out-of-sync Muriel, this odd Australian movie has an undeniable charm (much like Muriel herself). Offbeat and awkward on purpose, you’ll understand its cult classic status once you watch it.
Fun Fact: This movie’s all-ABBA soundtrack was so popular all over the world, that it directly led to the creation of the jukebox musical Mamma Mia!
Synopsis: An awkward, earnest young woman named Muriel from Porpoise Spit, NSW marries a South African swimmer so he can emigrate to Australia.
The Adventures of Priscilla, Queen of the Desert (1994)
I don’t know how Australia produced two epic cult films in such a short time, but it did. While some of the language didn’t age particularly well, this movie did a lot to make drag a more mainstream part of culture, and to advance trans rights. Plus, it’s hilarious.
Fun Fact: The town of Broken Hill had a reputation of homophobia during filming and was featured in the movie as such. However, after the film’s success, the town rehabbed its image and now has an annual drag festival.
Synopsis: Two drag queens and a trans woman embark on a road trip from Sydney to Alice Springs to perform a drag show.
Empire Records (1995)
If you want 90s teen culture in a movie, look no further (sorry not sorry, Reality Bites). Liv Tyler is so gorgeous it hurts, but the whole cast stands out for their pure teenage-ness and the overall combination of earnestness and desire to be cool.
Fun Fact: The writer based the movie off her time working for a Tower Records in Arizona.
Synopsis: Follow the employees of a record store through a single day when epic possibilities clash.
Mr. Holland’s Opus (1995)
Did this play on ABC constantly in the 90s, or did I make that up? Regardless, this movie was so important to my family. It lionizes teachers while exploring the tough questions around art and identity.
Fun Fact: Despite the fact that the character uses rock to inspire his students, Richard Dreyfuss has publicly stated he hates Rock ‘n’ Roll.
Synopsis: A composer-turned-high school music teacher must wrestle with his legacy when his child is born deaf.
Party Girl (1995)
Look, the movie is tonally all over the place and doesn’t get as close to what it’s trying to say as others on this list. But the costumes – I am telling you – the costumes. If you’re into putting up with the choppy tone, there’s a lot to love here.
Fun Fact: The first movie to premiere in its entirety online! Seriously! In 1995!
Synopsis: A spoiled fashionable party girl gets a job at the library to prove she can stand on her own two feet.
The Birdcage (1996)
I cannot impress on you the influence this movie has had on my life. Starring two iconic comedians as gay lovers, the plot line is sadly still relevant today (which is even worse when you consider the original source material, La Cages aux Folles, came out in the 70s). But seriously, Nathan Lane will melt your heart.
Fun Fact: When Oprah Winfrey tried to “out” Nathan Lane on her show during the press tour, Robin Williams stepped in with a joke to protect Lane’s privacy.
Synopsis: The gay owners of a drag club in South Beach Miami have to tone it down when their son brings his fiancee’s staunch Republican Senator father over for dinner.
First Wives Club (1996)
Why won’t media let us see women in their 60s being awesome anymore? This movie could’ve started something huge! Instead we must appreciate it for what it is: the ultimate ode to long-term friendship.
Fun Fact: Goldie Hawn’s real Oscar appears as her character’s Oscar Award.
Synopsis: Three long-term friends unite to see revenge on their ex-husbands.
That Thing You Do! (1996)
Beautiful Liv Tyler take 2! This movie has a lot of cornball moments, but frankly I don’t care. It’s a great movie to watch with your grandma when you want something clean but not boring, and the title song is one of the ultimate ear worms.
Fun Fact: Tom Hanks wrote this movie to stave off boredom while on the press tour for Forrest Gump.
Synopsis: A group of young men in the 1960s write a hit song and try to stay friends through the trials of early fame.
Liar Liar (1997)
Ace Ventura put Jim Carrey on the map, but this film showed the world he can really act. Usually I find Carrey a bit too much for me, but the themes of this movie are so sweet it grounds his kookiness really well.
Fun Fact: Steve Martin was originally supposed to play the main character.
Synopsis: A smarmy lawyer gets a dose of reality when he can no longer lie.
Romy and Michele’s High School Reunion (1997)
Though Clueless has a bigger reputation, Romy and Michele’s girl power screed against heteronormativity has always held a special place in my heart. Though very, very silly, the movie has a lovely message about allowing yourself to be yourself.
Fun Fact: Despite their airhead characters, Lisa Kudrow and Mira Sorvino went to Vassar and Harvard, respectively.
Synopsis: Two party girls from Venice Beach try to reinvent themselves at their 10 year high school reunion in Arizona.
But I’m a Cheerleader (1999)
Indie filmmakers in the 90s did things with practical aesthetics that still stand out for their creativity and visual impact. This movie uses the pop art around the characters to add a really striking dimension to the story. Plus, it’s fun!
Fun Fact: Natasha Lyonne got drunk and got a tattoo on her shoulder the day before filming began.
Synopsis: The ultimate good girl cheerleader gets sent to a gay conversion camp when her parents suspect her of lesbianism.
Office Space (1999)
The ultimate ode to shitty jobs. Watching this movie has provided me with much catharsis at particularly shitty jobs. The technology may change, but the humiliating office politics do not.
Fun Fact: Milton’s coveted stapler was a prop made for filming, but after the popularity of the movie, Swingline began making them again.
Synopsis: Corporate workers in cubicle hell rebel against their corporate overlords.
Superstar (1999)
Though it’s last because of its place in alphabetical order, it’s fitting to close out this list with the movie that got my best friend and I through middle and high school. It’s so silly to tear up thinking about this ridiculous movie, but films like Superstar show how powerful art can come from anywhere and mean anything. Don’t get me wrong – it’s not great cinema. But for a funny, light-hearted, unserious movie, this one tops the list.
Fun Fact: Every car shown in the movie is a Volkswagen Beetle.
Synopsis: An odd young woman gets the chance of a lifetime at her Catholic school’s talent show.
