The 100 Best Comedies of the 1990s

The 100 Best Comedies of the 1990s

It was the decade of Bill Clinton and grunge. It was the decade of Friends and Seinfeld. It was the decade of Quentin Tarantino and competing volcano movies. And it was a decade in which Hollywood comedies got darker but also sometimes weirder or stupider. Bill Murray evolved into an indie icon. Jim Carrey and Adam Sandler were exciting new comic explosions that changed the comedy landscape. And, sorry to say, Kevin Spacey was a pretty big deal.

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Putting together a list of the 100 best comedies of the 1990s, I dug deep, occasionally bypassing “classics” that I don’t really like and focusing instead on movies that, fondly remembered or not, I find funny. I decided not to include any documentaries, and I also avoided movies that, while featuring plentiful laughs, aren’t really comedies. (My apologies to fans of Pulp Fiction and The Ice Storm, two movies I deeply love.) Some of the people behind these movies have proved themselves to be terrible individuals, but I chose to stick with what was on the screen. Bottom line: To get on this list, you had to have stood the test of time. Much of the fashion and popular entertainment of the ‘90s now look terribly dated, but these 100 films have outlived the decade that inspired them. 

Slums of Beverly Hills (1998)

Natasha Lyonne has enjoyed a renaissance in recent years, but she first made a splash in writer-director Tamara Jenkins’ look at an unhappy 1970s teen trying to make sense of her life. The biting sarcasm, the world-weary exhaustion, the crack comic timing: Lyonne already had it all in Slums of Beverly Hills, bringing that same irreverent flair to recent works like Russian Doll and Poker Face.  

The Ref (1994)

The late Ted Demme directed this snarky dark comedy, in which Denis Leary plays a burglar on the run, taking hostage a miserable married couple (Judy Davis and Kevin Spacey). Soon, Leary has to play counselor to this bickering pair, resulting in some of the most caustic back-and-forth barbs of the decade. See it with someone you (don’t) love.

Austin Powers: International Man of Mystery (1997)

Others had tried to come up with a parody of James Bond flicks. But Mike Myers found the winning formula, not just mocking 007 but the Swinging Sixties era that he represented. In the process, Myers created an indelible character that made millions laugh — even if it never made them horny.

The Brothers McMullen (1995)

Ed Burns, who wrote, directed and starred in The Brothers McMullen, was taken aback by some of the people who responded to his Sundance smash. “There’s this one metalhead guy, someone who I would never have expected to like this kind of romantic film,” he recalled. “But he loved it because he said it’s a romantic comedy that guys can get into ‘cause the men in the film aren’t really like these wussy types. They’re these big bullshit-for-brains … like, you know, you or me or anyone.” By populating his film with working-class regular dudes — outwardly tough but inwardly sensitive — Burns struck a nerve with audiences that weren’t usually hanging out at the arthouse.

Go (1999)

If Doug Liman’s directing debut Swingers was widely viewed as writer Jon Favreau’s movie, Go helped establish the sort of filmmaker Liman would go on to become. A funny, thrilling Tarantino-esque look at a group of disparate characters set around Christmas, the movie launched the career of Sarah Polley, sending viewers on a drug-and-crime-infused ride. In its own way, Go is one of the 1990s’ most 1990s-ish films — a pivotal scene takes place at a rave. 

The Big Lebowski (1998)

A pseudo-noir comedy that imagines what would happen if Raymond Chandler wrote a mystery fronted by a stoner, The Big Lebowski may end up being Joel and Ethan Coen’s most enduring comedy, a quirky saga in which the Dude (Jeff Bridges) gets involved with some strange characters. (To be fair, though, the Dude’s actual friends, played by Coen regulars John Goodman and Steve Buscemi, are fairly odd themselves.) The film was never a monster hit, but it inspired a cult following that has endured for decades, turning nearly every line into a quotable gem. 

Strictly Ballroom (1992)

Here’s where Moulin Rouge! and Elvis director Baz Luhrmann first made his feature directorial debut, telling the story of an unconventional choreographer (Paul Mercurio) and the inexperienced new dancer (Tara Morice) he takes under his wing. The razzle-dazzle that went to 11 in his later films was already on display in Strictly Ballroom, but this remains his funniest movie — his sense of humor would often get squashed the more visually opulent his films got.

What About Bob? (1991)

“Funny movie. Terribly unpleasant experience.” That’s how Richard Dreyfuss described what it was like to make What About Bob? “We didn’t get along, me and Bill Murray. But I’ve got to give it to him: I don’t like him, but he makes me laugh even now.” As a troubled patient who decides to invade his shrink’s family vacation, Murray delivered a masterclass of irritation-inducing comedy. You really believe that Dreyfuss wants to slug him!

The Adventures of Priscilla, Queen of the Desert (1994)

Before the world knew Guy Pearce or Hugo Weaving, they were in this Australian comedy, alongside Terence Stamp playing drag performers on the road. Decades later, Priscilla continues to be a pivotal movie for young LGBTQ+ individuals, who see themselves in the film’s celebration of being yourself. “I still get 30 letters a week from people saying, ‘Thank you,’” writer-director Stephan Elliott said in 2021. “Particularly parents of gay kids who say, ‘Thank you for helping me understand.’”

CB4 (1993)

Although CB4 targeted the macho posturing of gangster rap, star and co-writer Chris Rock had nothing but love for the genre. “Rappers are the closest thing to being actual free Black people,” he said at the time. “Most Black people have a job where they have to answer to white people in some way. Everything I write has to go through this white system, and it has even affected my writing somewhat because I know white people are going to judge it. But rappers — it’s not that they hate white people — they don’t care.” This Spinal Tap-esque mockumentary cared a lot about being deeply silly and secretly smart. 

Wayne’s World (1992)

“Did you ever find Bugs Bunny attractive when he put on a dress and played a girl bunny?”

Sleepless in Seattle (1993)

The pinnacle of the Tom Hanks/Meg Ryan on-screen courtship, director Nora Ephron’s funny, wistful love story steals from An Affair to Remember, following two decent people as they find their way to one another. Poor Bill Pullman, playing Ryan’s fiancé, never had a chance. 

Analyze This (1999)

Director Harold Ramis’ last great film was this comedy about a mob boss who goes into therapy. Sound like The Sopranos? Well, Analyze This was being filmed around the same time as that show’s first season, with The Sopranos premiering about two months earlier. Nonetheless, the pairing of Robert De Niro and Billy Crystal played to each actor’s strengths, and the movie was a massive hit — leading to a sequel that wasn’t nearly as successful commercially or creatively.

My Cousin Vinny (1992)

Relative newcomer Marisa Tomei won Best Supporting Actress for her inspired performance as Mona Lisa, the brassy fiancée of Vinny (Joe Pesci), a New York lawyer who travels to Alamaba to defend his cousin and the cousin’s buddy, who are on trial for murder. Comedic performances rarely earn Oscars, but Tomei was simply too good. (Even more remarkably, that was My Cousin Vinny’s only nomination.) Tomei has gone on to an illustrious career, but she’s never been as hysterical as she was here.

As Good as It Gets (1997)

Jack Nicholson and Helen Hunt both took home Oscars for this dysfunctional rom-com about an OCD sufferer and a kindly waitress. As Good as It Gets was the last time (to date) that director James L. Brooks would receive Oscar nominations for one of his films, and while it’s not as sparkling as Broadcast News, the movie is a quirky, painfully funny comedy about unhappy people looking for a little something that might make life worth living.

Half Baked (1998)

Dave Chappelle, who wrote Half Baked with his creative partner Neal Brennan, wasn’t happy with the finished film. “(I)t was a real cool script," Chappelle later said. "And then I saw it, I was like, ‘Hey, man, you made a weed movie for kids,’ and it wasn’t for kids.” Many would disagree, judging it as one of the great stoner comedies of the 1990s. As director Tamra Davis told Cracked, “I remember being told once that Blockbuster said Half Baked was their most stolen movie ever, which, I mean, that’s just the greatest.”

Tommy Boy (1995)

This movie is very funny, but now watching it, it’s really sad. We’ll never know what Chris Farley could have become.

Father of the Bride (1991)

For fans who grew up on his hip, ironic comedy, it was a shock to see Steve Martin play a dad in this remake of the Spencer Tracy classic. But Martin was never more endearing than as George, the worried father who just wants his daughter’s wedding to go well. With Martin Short as the outrageous wedding coordinator, Father of the Bride became a generational staple as much as the 1950 film had been for a previous age.

Pretty Woman (1990)

Right, we’ve all heard the story that Pretty Woman’s original script was far darker, telling a more realistic story about a sex worker. But what ended up on screen is so damn charming, who cares? Julia Roberts became Julia Roberts with this film, charming the socks (and other items of clothing) off Richard Gere’s all-business corporate raider. Sometimes, we just want the fantasy. 

American Beauty (1999)

Overrated? Yeah, probably. Undeserving winner of Best Picture? Certainly. And yet, this spiky portrait of suburban despair still gets its hooks into you, thanks to Kevin Spacey as a DGAF dad and Annette Bening as his hyper-intense wife. Not long after, Oscar-winning screenwriter Alan Ball would give the world an even more beloved tale of family despair, Six Feet Under.

Dumb and Dumber (1994)

But they’re really funny idiots!

Quick Change (1990)

It’s hard to love this underrated heist comedy as much now that we know what a jerk Bill Murray was to Geena Davis during production. But Quick Change — which starred Murray, Davis and Randy Quaid, who played crooks who discover that robbing a bank in New York is way easier than getting out of the city — remains a tart delight. The film represents a fascinating transitional period in Murray’s career — moving from broad comedies to the more mature work he’d soon be focusing on — and it’s filled with snotty, sarcastic one-liners. It’s also the only movie he’s ever directed, alongside screenwriter Howard Franklin. Quick Change bombed at the box office, but a lot of us still remember it fondly — although I understand why Davis would not. 

Delicatessen (1991)

French filmmakers Jean-Pierre Jeunet and Marc Caro blew minds with this wicked, surreal dark comedy, set in a bleak future, about the denizens of an apartment complex. With shades of Soylent Green and more than a smattering of cartoon energy — which made sense considering the directors previously worked in animation — Delicatessen generated its considerable humor from its deeply weird vision. Midnight-movie crowds happily ate it up.

Wag the Dog (1997)

Director Barry Levinson stumbled more than soared during the 1990s. (He was responsible for duds like ToysJimmy Hollywood and Sphere.) But he hit the bull’s-eye with this satire in which a Robert Evans-like producer (Levinson’s Rain Man star Dustin Hoffman) and a sly strategist (Robert De Niro) scheme up a fake war to sell to the American public to distract from the president’s sexual misconduct. Wag the Dog was the kind of on-point look at the egos and idiocy of politics that we now get on the regular from Armando Iannucci.

The Dinner Game (1998)

In this French comedy, accountant Francois (Jacques Villeret) thinks he’s the guest of honor at a special invitation-only dinner party — but, in fact, he’s part of a cruel prank. (Each member of the elite club brings along the biggest idiot they can find, competing to see which guest will be deemed the “winner.”) The Dinner Game was a witty attack on the snobby and the rich, which was turned into the very unfunny American comedy Dinner for Schmucks

The Last Days of Disco (1998)

“There’s something really sexy about Scrooge McDuck.”

Three Kings (1999)

“Are we shooting people, or what?” 

The Birdcage (1996)

Would audiences go see a movie featuring two gay characters? That was a legitimate question in 1996, when this remake of La Cage aux Folles hit theaters. It helped, of course, that one of them was played by superstar Robin Williams, who along with Nathan Lane gave viewers one of the best portraits of a loving, imperfect couple that decade. At a time when tolerance was hardly at an all-time high — remember, this was the age of “Don’t ask, don’t tell” — The Birdcage broke down barriers while delivering big laughs.

Clerks (1994)

Kevin Smith was a poet of the slacker class, understanding the rhythms of going-nowhere dudes who work meaningless jobs and argue about which Star Wars sequel is better. Clerks mocked but also loved its convenience-store losers, viewing them as endearing weirdos who mean well. People of this ilk would go on to be the protagonists of so many of his later films. 

Swimming With Sharks (1994)

Everybody who worked as an assistant for a studio exec in the ‘90s knew this movie by heart.

Welcome to the Dollhouse (1995)

Long before there was a term for it, writer-director Todd Solondz mastered the art of cringe comedy with his second feature, which starred newcomer Heather Matarazzo as an unlovable tween trying to get the world to pay attention to her. No life lessons, no sentimental flourishes, no pat happy endings: Welcome to the Dollhouse was a poisonous film about how terrible growing up is. Solondz only got darker and more misanthropic from there.

Your Friends & Neighbors (1998)

Trying to make an even more scathing look at love than In the Company of Men, writer-director Neil LaBute focused on a group of terrible New Yorkers who inflict their romantic pain on one another. Jason Patric’s monologue about what he did to a male classmate will haunt you the rest of your days — that, and Ben Stiller’s horrible dirty talk. 

Toy Story 2 (1999)

What was Pixar thinking, making a sequel to its most perfect movie? Don’t worry: This was back when the studio couldn’t miss, delivering a deeply satisfying follow-up to the original Toy Story. Since then, there have been two more sequels, each one a worthy new chapter in a peerless franchise. 

Jerry Maguire (1996)

Containing arguably Tom Cruise’s finest pure comedic performance, Jerry Maguire featured the megawatt star, for once, playing an ordinary guy — more specifically, a high-powered sports agent who, after a crisis of conscience, ends up accidentally setting his career on fire. Turns out, Cruise can be really funny and charming as someone who’s been humbled by life — and, of course, Cuba Gooding Jr. won the Oscar for his role as Jerry’s irrepressible wide receiver client. 

Ed Wood (1994)

Johnny Depp was delightful as cinema’s most infamous terrible director. Martin Landau won Best Supporting Actor playing the struggling, aging actor Bela Lugosi. The affectionate, hilarious Ed Wood celebrated the dreamers who never let a lack of inspiration stop them from making their bad movies. 

Three Colors: White (1994)

Before his death in 1996, Polish filmmaker Krzysztof Kieślowski completed a trilogy of films built around the three colors in the French flag, each movie corresponding to one of the color’s themes. Blue (“liberty”) and Red (“fraternity”) were more serious, but White was a sardonic comedy built around the notion of “equality.” And so we follow the story of Karol (Zbigniew Zamachowski), a loser who’s getting divorced by his beautiful wife Dominique (a pre-Before Sunrise Julie Delpy). He decides to get revenge in the most roundabout, ingenuous way imaginable, Kieślowski finding the humor in what it feels like to be dumped — and how vengeance doesn’t always play out like you’d expect. 

Postcards From the Edge (1990)

Carrie Fisher decided to write a book that was inspired by her battles with addiction and a difficult mother. The result, Postcards From the Edge, was an acclaimed comic novel, proving that she was more than just Princess Leia. The book was turned into a movie, which Fisher also wrote, starring Meryl Streep as the Fisher-like Suzanne and Shirley MacLaine as the Debbie Reynolds-esque mom. It’s a biting film about mother-daughter relationships and the shallowness of Hollywood — and it let Streep be funny long before roles like The Devil Wears Prada established her comedy superstar bona fides. 

The Full Monty (1997)

Anybody else hear Tom Jones’ version of “You Can Leave Your Hat On” out in the world and immediately think of this movie?

Mars Attacks! (1996)

An utterly snotty comedy about some bug-eyed aliens taking over an Earth populated by the stupidest, vainest, shallowest humans imaginable, Mars Attacks! best encapsulates director Tim Burton’s disdain for society. The film tanked, but he’s never been funnier in burn-it-to-the-ground mode. 

Spanking the Monkey (1994)

Finding the dark humor in suicide, masturbation and incest, writer-director David O. Russell announced himself with his debut, becoming one of the 1990s’ most exciting indie voices. Spanking the Monkey turned the creepy into the oddly resonant, and fellow newcomer Jeremy Davies latched onto a generation’s discontent playing a college student weirdly attracted to his ailing mother (Alberta Watson). To call this movie a Gen-X spin on The Graduate isn’t that far off. 

Chasing Amy (1997)

Times change, and what once seemed sorta edgy can eventually feel a little cringe-y. Take Chasing Amy, inspired by writer-director Kevin Smith’s own experiences, which starred Ben Affleck as a comic-book artist who falls for fellow artist Alyssa (Joey Lauren Adams). There’s just one catch: She’s gay. A sincere, funny comedy about a straight dude’s insecurity and confusion, Chasing Amy is far more interested in the Affleck character, but its shortcomings don’t entirely detract from a frank exploration of sexual fluidity. 

The Wedding Singer (1998)

Sure, Adam Sandler was funny, but could he be a credible romantic lead? The Wedding Singer answered that question. He’s incredibly lovable in this 1980s-set rom-com, in which he falls for Drew Barrymore’s kindly waitress. This is the best film these longtime buds have done together, and the period-era jokes are pretty choice — especially the one about Van Halen.

White Men Can’t Jump (1992)

After receiving kudos for Bull Durham, writer-director Ron Shelton turned to hoops for White Men Can’t Jump, about two small-time basketball hustlers trying to decide whether to grow up or not. Good friends Woody Harrelson and Wesley Snipes had a crack comic rapport, and the smack-talk on the court is glorious. Even Stanley Kubrick was a fan.

Scream (1996)

Horror was in bad shape when screenwriter Kevin Williamson and director Wes Craven decided to send up the genre. Scream was a slasher movie that made fun of slasher movies, the hoary tropes being called out and then used as plot points. Neve Campbell was great as the haunted, hunted Sidney, with David Arquette serving as expert comedic relief as the sweet, dumb cop. Scream’s joke was so good that it launched a series that’s rarely been as funny or shocking since. 

Grosse Pointe Blank (1997)

Going to your high school reunion can be fraught — especially if you’re a hitman dealing with some personal issues. John Cusack starred and co-wrote this cheeky crime-thriller that’s really a comedy about aging Gen-Xers having to face the fact that they’re not kids anymore. 

Romy and Michele’s High School Reunion (1997)

The other great 1990s comedy about going back to your high school reunion.

City Slickers (1991)

Fresh off the success of When Harry Met Sally, Billy Crystal cemented his film stardom with this sentimental but deeply amusing story of some New York buddies who decide to take part in a cattle drive to bring some excitement back into their ho-hum lives. Jack Palance won Best Supporting Actor as a surly cowboy, and City Slickers proved to be a massive hit, Crystal milking the fish-out-of-water premise for all it was worth. 

A League of Their Own (1992)

One of the great baseball comedies was also one of 1992’s biggest smashes. Big director Penny Marshall told the story of the all-girls baseball league that sprung up during World War II, with Geena Davis and Tom Hanks locking horns as a star player and a drunken, misanthropic manager. There’s no crying in baseball, A League of Their Own told us, and yet, this enduring crowd-pleaser can be a tearjerker on occasion. 

Bottle Rocket (1996)

Some prefer Wes Anderson’s debut to his later films because, at this early stage, his dollhouse-like aesthetic wasn’t yet so precise, his characters’ mannered dialogue not yet so codified. Even so, Bottle Rocket contains the DNA for everything this distinct director would later create, following three fairly clueless dudes (Owen Wilson, Luke Wilson and Robert Musgrave) who try their hand at thievery. Misfit heroes, strange subcultures, a subtle emotional throughline just below the surface: This comic charmer was the first draft for the gems Anderson would go on to craft. 

Living in Oblivion (1995)

Indie filmmaker Tom DiCillo had just had a movie fall through when he was drunk at a party, talking to a guy who was congratulating him on the project, not realizing it was now not going to happen. “You don’t know the first thing about making a movie, how hard and tedious and frustrating it is,” DiCillo remembered telling the person. “You can have an actress all ready to do a scene, and everything’s ready to go, it’s a scene you love — and at the last minute, someone drops the microphone into the shot.” A lightbulb went off, and DiCillo decided to make Living in Oblivion, a comedy about all the ways that indie filmmaking is a hilarious nightmare. Indie actor extraordinaire Steve Buscemi was the right guy to play the DiCillo-like director at the center of the storm.

Muriel’s Wedding (1994)

Or, The Movie Where Everybody Fell in Love With Toni Collette. The Australian actress had been doing some film and television work before Muriel’s Wedding, but this melancholy, ABBA-fueled comedy is where she broke through, playing the searching, lovable title character who’s looking for her happy ending. Once Collette moved to Hollywood, she earned kudos for more serious roles (The Sixth Sense, Hereditary), but she’s a born comic dynamo.

Clueless (1995)

Amy Hecklering, who had directed everything from Fast Times at Ridgemont High to Look Who’s Talking, had a thought: What if you set Jane Austen in modern times? You didn’t need to have read Emma to enjoy Clueless, which featured a star-making turn from Alicia Silverstone as Cher, a spoiled Beverly Hills teen who ends up becoming a good person. And this is the film where we first met the charm machine known as Paul Rudd, who doesn’t seem like he’s aged a day since. 

Metropolitan (1990)

Who’d want to spend 90 minutes listening to snooty, young, rich New Yorkers sit around and quip? If it was the debut of writer-director Whit Stillman, who also produced, you sure would. Metropolitan earned the filmmaker an Original Screenplay Oscar nomination, and the movie helped introduce the world to the witty, dry demeanor of rising stars like Taylor Nichols and Christopher Eigeman, who would soon become fixtures in Stillman’s oeuvre. 

Happy Gilmore (1996)

Billy Madison first showed moviegoers what the Adam Sandler manchild persona could look like on the big screen. But his follow-up was even funnier, with Sandler playing the titular hockey player who discovers he’s a dynamite golfer. (Well, he can drive the ball really far — the other parts of the game take him a little longer.) From Christopher McDonald as an all-time great comedy villain to that Bob Barker fight sceneHappy Gilmore is so full of iconic moments that Kanye West referenced it in his landmark early single, “Jesus Walks.” 

Shakespeare in Love (1998)

You know, even the greatest playwright to ever live had to bang out terrible first drafts, too. That’s the cheeky premise behind this Best Picture-winner, with Joseph Fiennes playing William Shakespeare, who’s struggling with his new work, Romeo and Ethel, the Pirate’s Daughter, which is going nowhere. Then he falls in love with Gwyneth Paltrow’s aspiring actress Viola. Shakespeare in Love was a rom-com for adults, interweaving comedy and swooning passion. 

Babe (1995)

Man, that pig is adorable. 

The Nightmare Before Christmas (1993)

For the record, I think it plays just fine as either a Halloween movie or a Christmas movie. That’s, in fact, why it’s so funny, blending the two holidays into a twisted comic/romantic mixture.

Love Jones (1997)

Starting out, aspiring filmmaker Theodore Witcher felt creatively stifled. “(T)he only sort of avenue of creative expression I had at the time was I fell into this world of underground poetry in Chicago,” he later recalled. “That world was very inspirational to me. After I left Chicago to work in show business in L.A., I thought (the underground poetry) milieu was so vivid that it could be a really exciting backdrop to tell this love story.” And along came Love Jones, a smart, sly rom-com starring Larenz Tate and Nia Long as poets navigating their attraction for one another. A commercial disappointment but now part of the Criterion Collection, it’s finally getting its due.

The Nutty Professor (1996)

Eddie Murphy had been in a string of misfires before The Nutty Professor, which reminded viewers (and maybe himself) how great he could be with the right material. Remaking the Jerry Lewis classic, and playing an assortment of characters, the fading superstar reinvented himself as a family-friendly box-office titan — for better or worse

There’s Something About Mary (1998)

In her rave review, film critic Manohla Dargis said of There’s Something About Mary, “their taste is as bad as their timing is exquisite.” She, of course, was referring to directors Peter and Bobby Farrelly, who here figured out how to marry gross-out gags to a sentimental romantic comedy. The scrotum-stuck-in-the-zipper scene you remember — the sweet, genuine chemistry between Cameron Diaz and Ben Stiller, you may not.

Office Space (1999)

“It’s not that I’m lazy — it’s that I just don’t care.” That line, uttered by Ron Livingston’s apathetic Peter, succinctly sums up writer-director Mike Judge’s sarcastic comedy about how, as the movie’s tagline announces, work sucks. Office Space failed at the box office, but anybody who’s been stuck at a cubicle in the last 25 years can relate to its vision of micromanaging bosses, bizarre coworkers and uncooperative printers. Some of the realities of office life have changed since the movie’s premiere, but the misery of the 9-to-5 remains depressingly, hilariously relevant.

Four Weddings and a Funeral (1994)

Writer Richard Curtis didn’t think Hugh Grant should play Charles, the British man who falls in love with Andie MacDowell’s charming American Carrie. “I thought he was too handsome,” Curtis later admitted. (His choice? Alan Rickman.) But he was outvoted, and Four Weddings and a Funeral became a hit, propelling Grant to stardom. Rickman is the better actor, but Curtis’ collaborators were right: Grant was the superior choice for this enduring romantic comedy.

Mother (1996)

“I love you.”
“I know you think you do.”

Death Becomes Her (1992)

Now mostly known as the answer to the trivia question “What movie did Robert Zemeckis direct before Forrest Gump?,” Death Becomes Her is a nasty little comedy about vanity. Meryl Streep and Goldie Hawn play former friends who have always competed for the same men, both of them resorting to a little black magic to remain eternally youthful and attractive. With Bruce Willis as the ineffectual plastic surgeon trapped in the middle of this twisted romantic triangle, Death Becomes Her was a brutal takedown of the ways in which Hollywood forces women to stay forever young. 

The Cable Guy (1996)

Jim Carrey and director Ben Stiller encouraged each other to go dark for this creepy tale of a cable guy who starts stalking one of his clients (Matthew Broderick). The Cable Guy ended the star’s commercial hot streak, but it’s now rightly regarded as a nervy portrait of a truly disturbed individual. What no one knew was that Carrey would keep pushing into that weird terrain later in his career.

Rush Hour (1998)

It’s a pretty simple concept: One cop is Black, one cop is from Hong Kong, and they don’t get along. Rush Hour exploited the racial/cultural differences between these characters, played with gusto by Chris Tucker and Jackie Chan, for an action-comedy that moved as fast as Tucker’s mouth. 

Rushmore (1998)

Before Wes Anderson’s second feature, Jason Schwartzman was merely actress Talia Shire’s kid. Then came Rushmore, his big-screen acting debut, where he played angry, brilliant teenager Max Fischer, who is in love with his teacher (Olivia Williams). Mentored by a drunken, depressed middle-aged man (Bill Murray), Max makes his big move, only to discover how frustrating adult love can be — while Schwartzman demonstrated how well he could fit in Anderson’s quirky universe, including to this day with 2023’s Asteroid City

House Party (1990)

At a moment when Black filmmakers like Spike Lee were gaining a toehold in Hollywood, writer-director Reginald Hudlin pitched an idea about a crazy teenage house party. But he didn’t want his film to be thought of as “just” a Black film. “Wanting to go to a party that your father doesn’t want you to is an American experience — it crosses generations and races,” Hudlin said about House Party. “Once you touch upon the human condition, people can get into it. If the themes you are dealing with are human themes, then there is no need to compromise the cultural authenticity of the film.” Turning rappers Kid ‘n Play into movie stars, House Party was a deserving crossover hit.

Big Night (1996)

A loving look at two Italian immigrant brothers trying to run a successful restaurant on the East Coast in the 1950s, Big Night gets lots of laughs from the tension between the accommodating businessman Secondo (Stanley Tucci) and the perfectionist chef Primo (Tony Shalhoub), who isn’t gonna add any goddamn meatball to his pasta dish. This story about family, love and finding home in a new land came out years before Shalhoub won a slew of Emmys and Tucci became one of the internet’s most beloved zaddys. 

Friday (1995)

What’s the secret to Friday’s classic status? “(E)verybody can be Craig and Smokey,” star and co-writer Ice Cube once said. “You can always kick it with Craig, the homeboy or homegirl, just kick it all day and trip off your neighborhood. That’s what people do every day. It strikes a chord there.” Indeed, the rapper and Chris Tucker were perfectly paired as buddies who have to deal with grumpy dads and mean drug dealers. That said, I’m not sure how much the movie has to say about gun violence — sorry, Cube.

Liar Liar (1997)

After working together on Ace Ventura: Pet Detective, Jim Carrey and director Tom Shadyac reunited for a more polished, less crass comedy about a slick, soulless lawyer who suddenly discovers that he’s incapable of lying, leading to all kinds of wacky hijinks and touching life lessons. Carrey may have dialed down the immature antics a touch for Liar Liar, but he’s still an inspired, rubber-y presence, his deceitful character battling his honest mouth, which keeps getting him into trouble. 

Galaxy Quest (1999)

There are so many bad send-ups of Star Trek, but Galaxy Quest got it right, understanding why the franchise is so adored yet finding the humor in the obsessive fandom. Tim Allen was an excellent Shatner-like self-absorbed star, while Alan Rickman shone as the serious British actor mortified that this is how his career turned out. The action scenes are clever, and the jokes about celebrities, Hollywood, fanboys and cheap sci-fi effects never run out of gas. 

Bullets Over Broadway (1994)

Actors who play the Woody Allen character in his movies tend not to come off very well. (Let us pause now to recall Kenneth Branagh’s awful hemming-and-hawing Woody impression in Celebrity.) But John Cusack nailed it in Bullets Over Broadway, in which he portrayed a nervous, principled playwright in the 1920s who moves to New York to make his name, forced to cast the talentless actress of a mobster who’s helping to finance the production. The more Cusack’s character has to accept creative compromise, the funnier the film becomes — especially when Chazz Palminteri’s mob enforcer proves to be a better writer than he is. 

Fargo (1996)

Before Fargo, Joel and Ethan Coen were respected auteurs who had never fully been embraced by the Hollywood rank-and-file. Then came this dark comedy about a crime gone wrong and the pregnant sheriff determined to bring the bad guys to justice. Fargo earned the brothers their first Oscar, for Original Screenplay, and the film was nominated for six other awards, including Best Picture. (Frances McDormand⁣ took home the prize for Best Actress.) The violence was shocking, to be sure, but it was also very funny. And just the sight of the folksy Marge methodically unraveling the mystery was endlessly winning. 

Man on the Moon (1999)

The excellent 2017 documentary Jim & Andy: The Great Beyond chronicled how obsessively Jim Carrey channeled Andy Kaufman for this inspired biopic of the late comic provocateur. (Long story short: Carrey drove everybody on set nuts.) But the results speak for themselves: Man on the Moon is supremely funny while also commenting on a restless artist who kept inventing and reinventing, curious just how far you could stretch comedic premises without them breaking. 

Barton Fink (1991)

The panic and fear of writer’s block has never been dramatized on screen as hilariously (or as frighteningly) as in Barton Fink, in which the Coen brothers cast John Turturro as a pretentious 1940s playwright who’s lured to Hollywood to write for the pictures, resulting in creative stagnation and murder. Famously written in the midst of being stuck on their script for Miller’s Crossing, the film is surreal, funny and creepy, and John Goodman is divine as the next door neighbor from hell — perhaps literally.

Deconstructing Harry (1997)

Did Woody Allen base his self-loathing, cruelly brilliant author character on Philip Roth? Allen neither confirmed nor denied, but Deconstructing Harry is nonetheless a brutal takedown of a writer who has poured everything into his work, even if it hurts the people in the real world whose lives he steals from. Stars like Julia Louis-Dreyfus and Robin Williams were stellar, and although Allen was sometimes criticized for making movies that seemed cut off from their era, give him this: There’s a pretty cutting Bill Clinton joke in this.

Swingers (1996)

Jon Favreau first made his name as the writer and star of this hip comedy about a bunch of wannabe Hollywood players navigating the L.A. dating scene. And Swingers introduced us to the comic dynamo that was Vince Vaughn, who’s never been more uproarious than he was as Trent, the best/worst wingman you could ever ask for. Both of these guys had bright futures, and so did director Doug Liman, who went on to do The Bourne Identity and Mr. & Mrs. Smith.

Waiting for Guffman (1996)

Christopher Guest, Michael McKean and Harry Shearer, the geniuses behind This Is Spinal Tap, worked on songs for Guest’s delightful mockumentary about a bad community theater production. Waiting for Guffman gave plenty of funny people room to explore their improvisational side, including Bob Balaban, Catherine O’Hara, Parker Posey, Fred Willard and Eugene Levy, who co-wrote the film with Guest. To this day, I’m still annoyed that there aren’t My Dinner With Andre action figures. 

Gremlins 2: The New Batch (1990)

The original was more of a horror movie. But for the sequel, director Joe Dante decided to go satirical, placing the Gremlins (and Gizmo) in a Manhattan high rise and letting all hell break loose. Making fun of everything from sequels to musicals to film critics — Leonard Maltin provides a gleeful cameo as himself — Gremlins 2 is the kind of irreverent follow-up that no studio would ever allow today. (“What are you doing, Dante? We’ve got to protect the intellectual property!!!”) That’s just one reason why so many of us prefer it to the first film. 

Kingpin (1996)

Partly because it wasn’t the smash that some of their other 1990s comedies were, Kingpin is often considered the underrated great Farrelly brothers comedy. I’ll just say I think it’s their best, with Woody Harrelson as a cynical former bowling great and Randy Quaid as a sweet, dumb Amish man who’s also a master at the game. This road film also features Bill Murray as the wonderfully sleazy Big Ern, who arguably rocked the decade’s worst hairpiece. 

Flirting With Disaster (1996)

A modern screwball sex comedy, David O. Russell’s zany second feature stars Ben Stiller as a married man in search of his birth parents, getting the hots for the adoption case worker assigned to his case (Téa Leoni). With Patricia Arquette as his long-suffering wife, who also ends up with a wandering eye, Flirting With Disaster was equally horny and funny.

Glengarry Glen Ross (1992)

David Mamet adapted his Pulitzer Prize-winning play for the big screen, adding the now-infamous “Always Be Closing” monologue that Alec Baldwin knocked out of the park. Director James Foley took care of the rest, casting a murderers’ row of incredible actors — including Al Pacino, Jack Lemmon, Ed Harris and Alan Arkin — to deliver a shockingly profane and hilarious portrait of down-on-their-luck salesman over one desperate, tense night. Fun fact: Pacino won Best Actor for The Scent of a Woman, but he was far, far better that same year in this scorcher. 

Bowfinger (1999)

Often forgotten when people list the great Hollywood comedies, Bowfinger has a wonderful concept: Hacky producer Bobby Bowfinger (Steve Martin, who also wrote the script) wants to make a movie with eccentric superstar Kit Ramsey (Eddie Murphy), who wants nothing to do with the project, which is called Chubby Rain. (Can’t say I blame him.) Undaunted, Bobby launches a plan, telling the rest of the cast that Kit is doing the film but is such a method actor that he’s going to stay in character, requiring them to go up to the unaware Kit in real life and deliver their lines, all the while Bobby captures the interactions on camera. This, of course, is a terrible way to make a movie, but it results in a fantastically funny comedy about the paranoia, delusion and ego that power show business. 

South Park: Bigger, Longer & Uncut (1999)

Best musical of the 1990s. 

Defending Your Life (1991)

Writer-director Albert Brooks cast himself as a mediocre man who dies, discovering that, in the afterlife, you have to defend the choices you made on Earth in order to determine your ultimate fate. The Good Place took major inspiration from Defending Your Life, which featured Brooks’ warmest love story. (Meryl Streep has rarely been more enjoyably adorkable.) And Rip Torn’s terrific performance as Brooks’ backslapping, disingenuous lawyer set the stage for him playing Artie on The Larry Sanders Show.

L.A. Story (1991)

Sort of a West Coast response to Woody Allen’s ManhattanL.A. Story is Steve Martin’s comic valentine to the city he’s called home for decades. The film, directed by Mick Jackson based on Martin’s script, is about an unhappy weatherman who finds love with a London journalist (Victoria Tennant). Jokes about earthquakes, traffic, boob jobs, faddish restaurants and silly coffee drinks abound, but underneath it all is Martin’s most nuanced love story since Roxanne. Oh, and Sarah Jessica Parker is a riot as SanDeE*. 

To Die For (1995)

Before To Die ForNicole Kidman was known primarily as Tom Cruise’s wife — a decent actress but hardly a star. This stunning dark comedy changed that inaccurate perception for good. As Suzanne, a small-town weatherwoman with aspirations of being a big-time TV journalist, Kidman delivers a powerhouse performance. Suzanne’s plan involves some light murder, and Kidman’s cruelly manipulative turn opened the door for one of the great modern careers filled with daring star performances. Still, this remains her best comedic role — although it’s more darkly shocking than har-har hilarious. 

Dazed and Confused (1993)

Richard Linklater’s first film was the edgy Slacker, but for his follow-up, he mellowed out and went back in time. Dazed and Confused chronicles the last day of school for some Austin teens in 1976, tackling the topic American Graffiti-style as we meet a wide swath of burnouts and dreamers, horndogs and nerds. Few films did such a good job of spotlighting emerging stars: Ben Affleck, Milla Jovovich, Parker Posey and Matthew McConaughey got their start here.

Being John Malkovich (1999)

Hey, who’s this Charlie Kaufman guy with the really weird movie ideas? Being John Malkovich was the screenwriter’s debut, which imagined a portal that can send average people into the POV of acclaimed actor John Malkovich. The film was also the debut for director Spike Jonze, who brought the surreal, hilarious idea to vivid life. Bonus points for the incredible Charlie Sheen cameo.

The Truman Show (1998)

In retrospect, it’s inaccurate to call The Truman Show Jim Carrey’s first “serious” role. (There’s still a lot of humor here.) But by hooking up with Witness filmmaker Peter Weir, the Ace Ventura comic was clearly looking to challenge himself, starring as a man who doesn’t realize his entire life has been a reality show. Prescient and disturbing, The Truman Show paved the way for the risky parts Carrey would take in the years to come.

Men in Black (1997)

A sci-fi spectacle that’s also a buddy comedy, Men in Black had the genius idea of pairing wild card Will Smith with crotchety Tommy Lee Jones. The sequels weren’t nearly as good, but this first chapter remains one of the greatest, funniest action blockbusters. And the theme song’s pretty damn great, too.

Groundhog Day (1993)

Original Groundhog Day writer Danny Rubin was wondering about vampires when inspiration struck. “What would you do for an eternity?” he remembered thinking. “How long would it take before it stopped being fun or interesting or worthwhile? How would an eternally long life affect a person, particularly one who seemed incapable of change within his own normal lifetime?” Out of those musings came an idea for a cynical weatherman (Bill Murray) who finds himself repeating the same day, desperately trying to figure out how he can break the cycle. The movie helped establish Murray’s more philosophical, heartfelt side, setting the stage for his segue into indie comedies over the next decade. 

The Player (1992)

Robert Altman stuck it to Hollywood with this showbiz satire, based on the Michael Tolkin novel, that starred Tim Robbins as a soulless executive who accidentally kills a writer (Vincent D’Onofrio) and then begins an affair with the dead man’s girlfriend (Greta Scacchi). Some of The Player’s best jokes are its throwaway moments, like when Buck Henry, playing himself, pitches the studio a sequel to The Graduate that’s so terrible it’s amazing it hasn’t actually happened in real life yet.  

In the Company of Men (1997)

Arguably no film better encapsulated the anger and misogyny of the 1990s man than In the Company of Men’s classic line: “Let’s hurt somebody.” Playwright Neil LaBute made his feature directorial debut with this scathing portrait of two working stiffs (Aaron Eckhart and Matt Malloy) working at a branch office in the Midwest, each of them deciding to take out their sexual frustration on a pretty local (Stacy Edwards) they try to convince they’re in love with. A takedown of sexism and racism in the white-collar world, In the Company of Men predates Mad Men but has as much contempt for that insular, smug universe.

Hot Shots! (1991)

Jim Abrahams, part of the famed ZAZ trio, directed this gleeful Top Gun parody on his own, recruiting Charlie Sheen to play Topper Harley, a cocky flyboy with a troubled past. This supremely stupid comedy, co-written by Pat Proft, finds jokes anywhere, including a truly ridiculous running gag about a chihuahua, which somehow blends perfectly with homages to everything from The Fabulous Baker Boys to Dances With Wolves to 9 1/2 Weeks. If you ever needed a movie that could explain to you what a crock pot is for, you’re in luck. 

Husbands and Wives (1992)

Just as Woody Allen’s personal life was becoming tabloid fodder — he and his leading lady Mia Farrow were splitting up, the actress discovering he was dating her adopted daughter Soon-Yi Previn — the Oscar-winner dropped this scathing look at marriage and commitment, focusing on one couple who are ending things (Judy Davis and Sydney Pollack) and another recovering from the shock of their friends’ separation (Allen and Farrow). Husbands and Wives is one of Allen’s angriest comedies, viewing love as hopeless, designed to make people miserable. You don’t so much laugh at the barbs as you wince.

Toy Story (1995)

Forget the innovations Pixar’s feature-length debut brought to computer animation — it also raised the bar for comedy in kids’ films. Toy Story set up a classic showdown between Woody (Tom Hanks) and Buzz (Tim Allen), two very different toys who have to share the same playroom, and the film is filled with bits, one-liners, sight gags and clever riffs on some of your favorite toys. A beloved franchise was born. 

Election (1999)

“I always thought we were just making a nice little comedy with some realistic and hilarious characters,” director Alexander Payne once said about his adaptation of the Tom Perrotta novel, “so I was surprised later when many viewers saw it as a political metaphor.” No matter how deep you want to read Election, what’s obvious is that its depiction of a bloodthirsty high-school presidential election spoke to something profound about America’s competitive, ambitious spirit. Reese Witherspoon was never funnier — no offense, Legally Blonde fans — and Matthew Broderick was perfection as a mediocre middle-aged teacher determined to ensure she loses. No Payne comedy stings as painfully or with such frequency. 

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