The 1990s was one of the best decades for comedy movies, but plenty of hilarious classics slipped by without much notice and are worth revisiting in the modern day. Following the squeaky-clean 1980s, the ’90s were noticeably more gritty and rebellious, and that was especially reflected in the decade’s cinema. Though much of the mainstream Hollywood output was still the usual safe fare, filmmakers began making genre-defining movies on the fringes, which would come to define the ’90s spirit. Comedy was particularly popular during the period, and a wide range of voices contributed to the ’90s comedy style.
Whether it was grounded romantic comedies that showed the struggles of modern dating, or raunchy cringe-inducing black comedies that pushed the limits of taste, the ’90s had something for every viewer. Small-budget indie comedies had as much play as big-budget projects, and there was an egalitarian atтιтude toward the genre that didn’t exist before and hasn’t returned since. Despite the genre’s widespread appeal, the ’90s also produced its fair share of underseen gems, and some of the decade’s best comedy movies don’t get talked about enough in the modern day.
10
But I’m A Cheerleader (1999)
A Queer Comedy Classic With Natasha Lyonne
’90s comedies were often on the cutting edge, and 1999’s But I’m a Cheerleader is an important piece of queer representation in film. Natasha Lyonne appears as the straight-laced teen, Megan, and the movie brilliantly skewers conservative atтιтudes towards the LGBTQIA+ community at the time. The movie caused a small stir at the time of release, and faced heavy scrutiny from the MPAA.
But I’m a Cheerleader turns a gay conversion camp into the setting for a touching coming-of-age story, and supporting performances by the likes of RuPaul and Melanie Lynskey nearly steal the show. The film’s colorful approach and whimsical atтιтude clash hilariously with the film’s darker undertone about queer oppression, and it borrows all the best elements from John Waters’ movies.
9
The Last Days Of Disco (1998)
A Quirky Look At The End Of An Era
The Last Days of Disco may not be as uproarious as other comedies, but its droll humor and witty dialogue make for a great watch.
Director/writer Whit Stillman’s 1990s comedies existed at the fringe of popular culture, and his approach to storytelling essentially excludes them from the mainstream. However, 1998’s The Last Days of Disco is perhaps his most accessible film, due in large part to the performances of co-stars Chloë Sevigny and Kate Beckinsale. Lacking a conventional plot structure, the movie is more about Alice and Charlotte’s adventures in the city as the ’70s gives way to the ’80s. The Last Days of Disco may not be as uproarious as other comedies, but its droll humor and witty dialogue make for a great watch.
8
Election (1999)
Reese Witherspoon At Her Very Best
A few years before she would become a megastar, Reese Witherspoon turned in one of her best performances in Election. Witherspoon was perfectly cast as the dastardly and precocious Tracy Flick, and director Alexander Payne delivers a тιԍнтly-paced comedy that has all the twists and turns of a political thriller. What could have been a simple late-’90s romp is actually something much deeper, and Election isn’t afraid to push the envelope.
Election was nominated for an Academy Award for Best Adapted Screenplay.
Using light satire and a touch of raunchiness, Election challenges the viewer’s expectations as the story progresses. What starts out as a funny, but justifiable, decision on the part of Matthew Broderick’s Jim McAllister eventually becomes a deeper commentary about the nature of ethics in general.
7
Bob Roberts (1992)
A Biting Political Mockumentary With An All-Star Cast
The mockumentary was a popular sub-genre in the 1990s, but Bob Roberts is often overlooked. Tim Robbins stars as the тιтular would-be senator who is running an unorthodox far-right campaign, and will seemingly stop at nothing to win. The movie brilliantly uses its faux documentary style to tell its story, and it delivers laughs in ways that a more conventional film couldn’t. Politics aside, the movie cleverly predicts the shifting approach to media in the new decade, and features a ton of hilarious performances from the likes of Alan Rickman and a very young Jack Black.
6
To Die For (1995)
Nicole Kidman Proves That She’s A Star
To Die For blends mockumentary with conventional filmmaking to tell a complex story through various conflicting lenses.
Director Gus Van Sant had already proven himself to be an indie darling by the mid-’90s, but To Die For is an example of the filmmaker at his very best. The pitch-black comedy stars Nicole Kidman as a small-town TV news reporter who will do anything to achieve stardom, and it ranks among her greatest work from any era. To Die For blends mockumentary with conventional filmmaking to tell a complex story through various conflicting lenses.
Echoing the tabloids that covered the actual news story the movie is loosely based on, To Die For uses dark comedy to pick apart media sensationalism. The laughs don’t come from outright jokes; instead, the movie creates humor through the ridiculous situation, and the juxtaposition of crime with over-the-top characters.
5
Welcome To The Dollhouse (1995)
A Quintessential 1990s Cringe Comedy
Comedy was a weapon in the ’90s and few films knew exactly how to ratchet-up the cringe quite like Todd Solondz’ Welcome to the Dollhouse. Heather Matarazzo plays an outcast youngster, Dawn Weiner, who can’t catch a break at home or in the complicated social world of middle school. Unlike earlier tween or teen comedies, Welcome to the Dollhouse is squirm-inducing in its unflinching reality, and there’s no Hollywood gloss on Dawn’s day-to-day foibles.
Solondz’ films aren’t afraid to push the boundaries into territory that’s often considered off-limits, but Welcome to the Dollhouse is the perfect blend of character-driven comedy and edginess. Dawn is a likable, if very flawed, main character, and she’s truer to real-life awkward tweens than many of her cinematic counterparts.
4
Party Girl (1995)
Parker Posey In One Of Her Most Iconic Roles
There was an explosion of subcultures in the ’90s, and Party Girl encapsulated a small corner of the era’s club scene in New York City. Mixing ’90s slacker aesthetic with big-city absurdity, Party Girl cast Parker Posey in the perfect role as a rave queen who is forced to work a boring job. The art-house classic takes aim at the disaffected atтιтude of the decade, while also paying tribute to the free-spirited nature of a city that was slowly becoming more commercialized. Party Girl is a time capsule to another era, but it is also a clever and hilarious comedy.
Party Girl was the first theatrically released feature film in the US to premiere on the internet.
3
Love Jones (1997)
An Underrated Romantic Comedy From A Decade Known For Rom-Coms
Black cinema entered a new era in the 1990s, and the romantic comedy Love Jones is a highlight from a decade known for its rom-coms. Though the meet-cute situation between Darius and Nina is not particularly original, the story of the trials and tribulations of their love-affair makes for humorous and compelling viewing. The movie has a lyrical quality that most Hollywood rom-coms of the time lacked, and Love Jones balances its tones without tipping too far into sappy melodrama or over-the-top laughs.
2
The Daytrippers (1997)
An Understated ’90s Comedy
Low-budget independent films were able to find larger audiences in the 1990s, and Greg Mottola’s debut feature perfectly encapsulated the decade’s spirit. The Daytrippers is an unconventional all-in-one-day story, about a family coming together to catch a potentially cheating husband. Like most great journeys, the point is actually the trip and not the destination, and the characters’ shortcomings are fodder for the film’s sense of humor.
Echoing the other great comedies of the decade, The Daytrippers is able to mix comedy with drama quite effectively, and the тιтular day trip has actual stakes. Because the film was made on the cheap, it’s the performances that really shine, and the small ensemble (including Parker Posey, Liev Schreiber, and Stanley Tucci) carries the material to the hilarious finish line.
1
Reality Bites (1994)
Ben Stiller’s Directorial Debut Is A ’90s Staple
There was a big shift in cultural atтιтudes as Gen X began to take center stage in the 1990s, and Reality Bites may be the ultimate Gen X movie. Directed by Ben Stiller, the film chronicles its post-collegiate characters as they try to find meaningful relationships in an increasingly disinterested world. Effortlessly touching on heavy topics, Reality Bites distills the zeitgeist of the mid-’90s into a digestable feature film.
The movie was a modest hit and was critically regarded, but was perhaps a bit too real for most audiences at the time. Nostalgia has shaved off some of the darker aspects of the decade, but Reality Bites leans into them for a much more realistic approach. Comedy movies are often the best medium for tackling complicated issues, and Ben Stiller’s debut found the right recipe of humor and heart.
