The 30 Best Comedies of the 1990s

best 90s comedies

Carrying on from Taste of Cinema’s recent list of the 30 Best Comedies of the 1980s is this similarly sentimental and purposefully playful look back at the 1990s. There’s a degree of idiosyncratic retrospection with the following list of populist funny films, each endearing and enjoyable in their own way.

The 1990s saw, especially in North America, the rise to superstardom of such comedy kings and queens as Jim Carrey, Mike Myers, Cameron Diaz, Kevin Smith and many others. And while one can endlessly debate about which films were funniest, those represented here reflect not just successful box-office tallies, but cultural touchstones, recognizable and ridiculously quotable lines, and influential trends that still resonate amongst comedy fans today.

Please note that there were, of course, many wonderful films that didn’t make the list––distilling such a prolific decade into a scant 30 film choices is no small charge––so if inclined, please do continue this discussion of great 1990s comedies in the comments section below. So now sit back and wax nostalgic with us as we explore the funniest films from an affecting and endearing decade…


30. Clerks (1994)

Here’s the film that started it all for Kevin Smith––is it too glib to suggest he peaked with this dialogue-driven debut?––and his View Askewniverse. This shoestring budgeted, foul-mouthed entrée was famously partially financed by Smith’s own extensive comic book collection.

Shot at the convenience store and neighboring video store where Smith worked for a number of years, the DIY inventiveness, crass humor, matter-of-fact black-and-white photography, and deadpan comic panache is hard to traverse. A film that helped define the slacker tenets of sarcasm and censure, with loads of pop culture posturing, Clerks is a welcome sale, a cult classic, and probably the highlight of Smith’s spotty (but funny) oeuvre.

To quote the jaded and self-inflated video store employee Randal Graves (Jeff Anderson): “This job would be great if it wasn’t for the fucking customers.”


29. Johnny Stecchino (1991)

Johnny Stecchino

Having already made a splash with American audiences via Jim Jarmusch’s brilliant 1986 indie arthouse comedy Down By Law, and already famous and familiar in his native land of Italy, Roberto Benigni saw another box-office success with this silly, slapstick, and rather charming crime comedy caper Johnny Stecchino. Directed and co-written by Benigni, Johnny Stecchino also represents one of several successful collaborations with co-star and wife, Nicoletta Braschi.

Dante (Benigni) is a bumbling but lovable school bus driver living in Rome who one day meets the mesmerizing Maria (Nicoletta Braschi), who quickly ropes him into coming to Palermo, Italy, with the promise of budding passions. But Maria, as it turns out, is married to a Mafia boss who’s a dead ringer for Dante, who goes by the name of Johnny Stecchino (also Benigni).

With the mob in pursuit of Johnny for turning into a two-faced snitch, Maria schemes in hopes the gangsters will mistakenly “whack” Dante instead, so she and Johnny can make a clean break. Hilarity ensues and Benigni’s knack for physical comedy soon takes center stage.

Johnny Stecchino’s North American release was limited but benefitted significantly from Jim Jarmusch’s wonderful portmanteau film Night on Earth (co-starring Benigni) being in theaters around the same time, and while a very different brand of comedy, both display Benigni’s gifts as gadfly, clown, and farceur.


28. Friday (1995)

Friday – F. Gary Gray

“I know you don’t smoke weed, I know this,” says Smokey (Chris Tucker) to his best friend Craig (Ice Cube), adding: “but I’m gonna get you high today, ’cause it’s Friday; you ain’t got no job… and you ain’t got shit to do.”

Now something of a classic in the stoner buddy comedy subgenre, as well as marking filmmaker F. Gary Gray’s (Straight Outta Compton) directorial debut, Friday was a surprise success and first in a profitable and charming comedic franchise.

Written by co-star Ice Cube and DJ Pooh (aka Mark Jordan), Friday unravels in LA on the eponymous end of the week as our hangdog hero Craig Jones (Cube) has just lost his job, owes some serious rent, his uppity girlfriend Joi (Paula Jai Parker) won’t get off his case, and he owes his best friend Smokey (Tucker) is in some major debt to the local drug dealer (Faizon Love).

Consistently crass, always energetic, and surprisingly nimble considering that Friday is populated by crackheads, trigger-happy homies, unprincipled pastors, and other unsavory aspects of urban living, this wise and wily semi-autobiographical slice of life will have you happily quipping “damn!” again and again.


27. Tommy Boy (1995)

Tommy Boy

At a glance, this familiarly plotted and largely predictable road movie may not seem particularly memorable or much to chuckle about––didn’t producer Lorne Michael, of Saturday Night Live fame, make dozens of these lowbrow comedies in the 90s?––but what makes Tommy Boy so laughable and likeable is the central performance from the late and beloved Chris Farley.

Farley, who passed away in 1997 owing to an accidental drug overdose at the too young age of 33 had left a successful run on SNL and was only starting out in making comedy features and this was arguably his most enjoyable and has enjoyed an enduring cult status because of it.

After the death of beloved patriarch Thomas “Big Tom” Callahan Jr. (Brian Dennehy), his half-wit son Tommy Callahan (Farley), the titular “Tommy Boy,” is suddenly heir to a nearly bankrupt automobile parts factory.

Throw into the mix Tommy’s greedy stepmother Beverly (Bo Derek), his dad’s conventional and uptight assistant, Richard (David Spade), a particularly plucky rival named Ray Dan Aykroyd), and a thin but blithe excuse for Tommy to hit the road––apparently to round up some new clients to save the factory––and some sweet natured situational comedy ensues. A must for Farley fans.


26. The Wedding Singer (1998)

For all his sophomoric and often quite foolish movies throughout the 90s and beyond, Adam Sandler’s distinct manchild characters grated on all but his most devoted fans, and yet with the surprise comedy smash of 1998’s The Wedding Singer, Sandler surprised even many of his detractors with this nostalgic, sweet, and even enticing romantic comedy.

Set in 1985, Robbie Hart (Sandler) is an amicable lost cause stuck in a rut as a wedding singer in the New Jersey suburbs. Jilted at the altar by his callous fiancé Linda (Angela Featherstone), Robbie somehow recovers from his heartbreak only to fall hard for one Julia Sullivan (Drew Barrymore), soon to be wed unless he can win her over.

Aided by an eclectic and sentimental soundtrack of 80s classic cuts as well as great comic turns from cast members Alexis Arquette, Christine Taylor, and a show-stopping cover of “Rapper’s Delight” from Ellen Albertini Dow, the Wedding Singer magically hits all the right notes.


25. The Full Monty (1997)


It seemed like the summer of 1997 it was impossible to leave your home and not hear Donna Summer’s “Hot Stuff” or Hot Chocolate’s “You Sexy Thing” and the main reason for this kitschy disco revival was Peter Cattaneo’s crowd-pleasing, feel-good British comedy-drama, The Full Monty.

As far removed as his terrifyingly abusive drunk Begbie from Danny Boyle’s Trainspotting (1996), Robert Carlyle leads this smart ensemble as a likeable though somewhat deadbeat blue collar steel factory worker named Gaz Schofield.

Having recently lost his job due to layoffs and having missed a number of child support payments and fearing a lawsuit from his reasonably outraged ex-wife (Emily Woof), Gaz and his good mate Dave Horsefall (Mark Addy) get the idea in their heads that they could create a profitable male strip-tease act.

Soon the likeable but unlikely duo have recruited their former foreman, Gerald (Tom Wilkinson), and a security guard named Lomper (Steve Huison) into their titillating troupe. Promising that their revue will attract an audience due to their willingness to go “the Full Monty”: completely buck naked.

A huge hit with audiences and critics alike––the film would also garner a number of Academy Award noms (including best picture, best director, and best screenplay), winning for Best Original Score, as well as sweeping the BAFTAs––as well as seeing a successful Broadway musical adaptation (2000) and a well-received play (2013), The Full Monty is an au naturel delight.


24. Home Alone (1990)

One of the biggest box office successes of the decade and responsible for making child star Macaulay Culkin a household name, director Chris Columbus and writer/producer John Hughes struck comic gold with Home Alone.

Amidst the holiday hoopla and commotion, 8-year-old Kevin McCallister (Culkin) is left “home alone” as his frazzled mother Kate (Catherine O’Hara) corrals her clan to the airport for the family Christmas trip to Paris.

Ushering everyone out to the airport and storming out in a huff––Kate doesn’t realize that Kevin is missing until mid-flight, just go with it––Kevin awakens to an empty house. Speculating that his wish to have no family has been somehow granted––he previously had a terrible row with his obnoxious older brother Buzz (Devin Ratray)––and Kevin’s excitement seems unbridled.

Of course this elation is short lived as two crooked con men known as “the Wet Bandits” (played by the hilarious duo of Daniel Stern and Joe Pesci) make plans to rob the McCallister residence, forcing Kevin to protect the family home with Three Stooges-inspired slapstick repercussions.

While largely aimed at a youth audience, Home Alone is great holiday fare if you can suspend disbelief and buy into a rather juvenile premise. Several sequels would follow but none contain the bite or the or the appeal of the original.