The 10 Best Comedy Movies of the ’90s, Ranked

The ‘90s were famous for a lot of things: presidential scandals, grunge rock, questionable fashion. But most importantly, the decade brought us some of the greatest comedies of all time. From films with dry wit to movies with over-the-top characters, the ’90s had us laughing until the world didn’t end on Y2K.

As a child of the ’90s and a self-proclaimed comedy expert, determining the greatest ten comedies was no easy task. In fact, tears were shed as some brilliant titles, like Big Daddy, Romy and Michele’s High School Reunion, and Drop Dead Gorgeous, were casualties and chopped. Nevertheless, we are here to celebrate these ten laugh riots. For those who love to laugh until they cry, these titles succeed. With quotable quotes, iconic characters, and moments that influenced future films, these ’90s comedies will forever go down in history as the best of the decade.

10

‘The Truman Show’ (1998)

Image via Paramount Pictures

Directed by Peter Weir, The Truman Show follows Jim Carrey as Truman Burbank, a man unaware that he has been living his entire life on a colossal soundstage, filmed and broadcast as a reality television show with a huge international following. All of his friends, family, and members of his community are paid actors whose job is to sustain the illusion and keep Truman unaware that the world he inhabits is scripted and fake.

Balancing some dramatic moments within the lighthearted comedy, The Truman Show broke down the terror of media manipulation through the ethics of reality television as one man seeks ultimate freedom. Here, Carrey used his humor to tap into the humanity of his character while experiencing some of the darker tones of the story. This performance carried him into the 21st century as he proved he could tap into both sides of acting. The Truman Show tapped into our obsession with watching fabricated, everyday lives, using the mundane to distract from the monotony. Because reality television is regarded as a top genre today, The Truman Show has a timeless quality that makes us all ponder, on our worst days, whether we might be experiencing our own Truman Show.

9

‘There’s Something About Mary’ (1998)

Image via 20th Century Studios

Ah, the rom-com. One of the most frequent sub-genres of the decade. While we had many that veered more into the romance than the comedy, There’s Something About Mary embraced both. Just look at the iconic image of Cameron Diaz and the hair gel. Directed by the Farrelly Brothers, the film follows a socially awkward man named Ted (Ben Stiller) who, 13 years after a disastrous prom night, hires a private investigator, Pat Healy (Matt Dillon), to track down his high school crush, Mary (Diaz). Only conflict arises as Healy falls in love with Mary and lies to Ted about her to prevent them from reuniting.

With slapstick humor and gross-out gags, There’s Something About Mary proved our great desire for raunchy rom-coms. For many audiences, rom-coms were almost too sickly sweet and sanitary to care about. There’s Something About Mary brought vulgar humor right to the edge, making it a bit more reflective of the reality of romance. Further, the common tropes were pushed to the side as it’s the man pursuing the woman. There’s a no-holds-barred sensibility that ensures there was no dull moment. Between the hair gel scene and the painfully hilarious zipper moment, truly, this delightful romp is non-stop funny.

8

‘Ace Ventura: Pet Detective’ (1994)

Image via Warner Bros.

If there’s one thing we learned from Ace Ventura: Pet Detective, it’s how a placeholder should hold a football: laces out! The film that truly put Jim Carrey on the comedy map was the 1994 hit by Carrey and Jack Bernstein. Eccentric private investigator Ace Ventura (Carrey) is hired to find Snowflake, the kidnapped dolphin mascot of the Miami Dolphins, right before the Super Bowl. Ace uncovers a conspiracy involving former player Ray Finkle, who is revealed to be disguised as Lt. Lois Einhorn (Sean Young), the lead police officer on the case.

A simple premise ripe for comedy, Ace Ventura was a showcase for Carrey to bring his physical humor and signature rubber-faced antics to a broader audience. Thus, it lives and dies with the manic titular character. With his distinct look and vocal affectation, Carrey created a fully rounded hero that was instantly identifiable, equal parts charismatic and bizarre. By leaning into classic mystery tropes with a very unlikely lead, the film simply worked and had an indelible impact on the decade and the comedies audiences wanted to see.

7

‘Clueless’ (1995)

Image via Paramount Pictures

From its signature fashion to our obsession with saying, “As if,” Clueless was the definitive teen comedy of the decade. A satirical, modernized version of Jane Austen’s Emma, Clueless tells the story of Cher Horowitz (Alicia Silverstone), a shallow but well-meaning Beverly Hills teen on a mission to do “good deeds.” She befriends newcomer Tai Frasier (Brittany Murphy), decides to give her a makeover, and plays matchmaker for her teachers, all while examining her existence.

Becoming synonymous with ’90s iconography, Clueless is a genuinely heartfelt coming-of-age comedy that set the tone for the remainder of teen comedies of the decade. It had a very specific aesthetic that was simply unmatched. Just like the slang and culture within, it’s become a ’90s time capsule on its own. As a work of subtle satire, Clueless made us care about the characters, as they were tremendously well-developed. A definitive period piece, the film’s legacy endures.

6

‘Austin Powers: International Man of Mystery’ (1997)

Image via New Line Cinema

Yeah, baby! One of the most beloved franchises of all time is James Bond. The ultimate spy was finally lampooned in the hit comedy Austin Powers: International Man of Mystery, a ’60s-tinged sex romp starring Mike Myers as the titular character, a groovy British secret agent frozen in time. He is thawed out in the 1990s to battle his arch-nemesis, Dr. Evil (Myers), who has returned to threaten the world after a 30-year cryogenic slumber. As Powers attempts to adapt to his new ’90s world, Dr. Evil plans to hold the world ransom with a nuclear weapon.

Raunchy in humor and stylish in aesthetic, Austin Powers: International Man of Mystery cemented Myers as a movie star. To say it’s a perfect parody of the James Bond series is an understatement, but if you don’t know the source material, Austin Powers lives on as a sole entity. The sharp satire and the unabashed, unafraid willingness to hurl sex humor all over the place made it such a profoundly funny flick. With so much to pull from, Austin Powers: International Man of Mystery spawned two sequels that catapulted it to the top of the box office. In the year of our Lord 2026, we certainly deserve another Austin Powers movie.

5

‘Waiting for Guffman’ (1996)

image via Sony Pictures Classics

If there’s one thing Christopher Guest is exceptional at, it’s mockumentary comedies. Easily one of his greatest was 1996’s theater-centric Waiting for Guffman. Alluding to Samuel Beckett’s Waiting for Godot, the film is about a quirky small-town community theater group in Blaine, Missouri, striving to put on a musical for the town’s 150th anniversary. They fixate on attracting a Broadway producer, Mort Guffman, believing he will propel their show, Red, White and Blaine, to stardom.

An ode to theater makers everywhere, every opening night we quote the film: “It’s the day of the show, y’all.” Like every other Guest classic, Waiting for Guffman thrives through the improv by the sensational ensemble. Joining Guest are many of his mainstays, including Eugene Levy, Fred Willard, Catherine O’Hara, and Parker Posey. The characters are endearing, with loving delusions of grandeur. Guest perfectly captures the spirit of a small town community. The final performance is awkward and cringy, but admit it, that’s the charm of community theater. Waiting for Guffman has many sensational sibling films in the 21st century, but the heart of the Guest aesthetic lies here.

4

‘The Big Lebowski’ (1998)

Image via Gramercy Pictures

When we think of Joel and Ethan Coen, we often point to their dramatic and darker films. But then, smack-dab in the middle is their crime comedy, The Big Lebowski, that reminds us they can do anything. In the bowling-centric movie, Jeffrey “The Dude” Lebowski (Jeff Bridges), a laid-back L.A. slacker mistaken for a millionaire philanthropist of the same name. After thugs soil his rug, The Dude seeks compensation, becoming entangled in a complex kidnapping plot involving a porn producer, nihilists, and the millionaire’s wife.

A send-off of film noir films of yore, The Big Lebowski is a character-focused film that just so happens to have a tightly plotted story to play within. It’s a complex comedic thriller with a taste for the surreal, a Western stoner as you’ve never seen before. The entire ensemble—Bridges, John Goodman, Julianne Moore, Steve Buscemi, John Turturro—crafted memorable characters that leapt through the screen, thanks to their ability to play within the Coens’ fully realized surrealist world. The Big Lebowski has grown into itself with a truly devoted fan base that has passed it down from generation to generation.

3

‘The Wedding Singer’ (1998)

Image via New Line Cinema

The early ’90s saw former Saturday Night Live star Adam Sandler lean into his man-child persona in many classic ’90s comedies. By the latter part of the decade, he continued to play fully developed, uniquely Sandler characters, but now they had some heart. In the ’80s-set The Wedding Singer, Robbie Hart (Sandler), a popular New Jersey wedding singer, is left at the altar, turning him into a cynical performer. He falls for Julia Sullivan (Drew Barrymore), a waitress engaged to a shallow, unfaithful Wall Street broker, Glen Gulia (Matthew Glave). Robbie must win her heart before she marries the wrong guy.

A story of romantic redemption and the journey to get there, The Wedding Singer is a wholesome romantic comedy that made us all love love. With a simple premise and quirky characters, it is an electric, charming film featuring a superb duo as the romantic leads. Sandler and Barrymore, who would go on to star in further films, struck the perfect chord. Through ’80s nostalgia, humor, and sentimentality, The Wedding Singer was more than a period piece; it was a timeless, tender tale that became a standout for both actors’ careers. Sandler has many great comedies, but The Wedding Singer stands atop.

2

‘Mrs. Doubtfire’ (1993)

Image via 20th Century Studios

If there were a Mount Rushmore of comedic film actors, Robin Williams would be etched in stone. Perhaps his most beloved film is the family classic, Mrs. Doubtfire. Directed by Chris Columbus, it tells the story of Daniel Hilliard (Williams), a divorced actor who disguises himself as an elderly British nanny, Euphegenia Doubtfire, to spend time with his children after losing custody to his ex-wife, Miranda (Sally Field). With his brother Frank’s (Harvey Fierstein) help, he manages the charade, becoming a better father while navigating chaotic, humorous situations, ultimately revealing his identity before securing joint custody.

Bringing hope to families of divorce, Mrs. Doubtfire is more than goofy; it’s grounded in humanity and authenticity. For many viewers, it was their first time watching a man in drag. Did they grasp that’s what it was? Likely not. In films like Some Like It Hot and Tootsie, you had to suspend disbelief to truly go along with the men in drag. Here, the makeup and costume design are so sublime that had you not seen the brilliant transformation scene, you might think it was real. By the end of the film, Mrs. Doubtfire becomes an inspiration to all who watch her. Mrs. Doubtfire is a brilliant film that will never grow old, a feel-good family comedy that will forever live in our hearts.

1

‘My Cousin Vinny’ (1992)

Image via 20th Century Studios/courtesy Everett Collection

Fish out of water films are not always inherently funny, but when it comes to My Cousin Vinny, it was hilarious. Easily the funniest film of the decade, two Brooklyn college students, Bill (Ralph Macchio) and Stan (Mitchell Whitfield), are wrongly arrested for murder at a convenience store in rural Alabama. They hire Bill’s cousin, Vinny Gambini (Joe Pesci), an inexperienced, newly minted lawyer, to defend them. Despite his lack of experience, Vinny and his sharp-witted fiancée, Mona Lisa Vito (Marisa Tomei), use unconventional methods and cross-examination skills to prove their innocence.

My Cousin Vinny may look like a typical courtroom procedural, but it goes beyond the basics. Of course, the judge is going to be a strict, hard-nosed Southern gentleman who demands Southern courtroom etiquette from a man who looks like he’s straight out of the mob. Is it too easy that the star witness is going to be the brilliant fiancée who’s a car expert? Perhaps, but without it, Tomei would not have shocked the world with her Oscar win. And let’s face it, “My biological clock is ticking” is one of the greatest movie quotes ever written. My Cousin Vinny is storytelling at its finest: crass, intelligent, and funny as hell.