The 1990s were a goldmine for hilarious comedy movies, and every year of the decade produced at least one all-time classic that is still uproariously funny today. Following the ’80s, where comedy really found its stride, the 1990s saw the genre go in an entirely new direction. Fresh voices in cinema took comedy to exciting new places with irreverent humor.

Though mainstream comedy was still popular, the 1990s also saw the rise of independent filmmakers who captured the zeitgeist of the decade. Slacker comedy movies had their finger on the pulse of Gen-X, while low-budget films weren’t afraid to say what Hollywood couldn’t. For the first time in history, there wasn’t a unified voice in comedy in the 1990s.

Despite the variety of comedy in the ’90s, they were all linked by a sense of humor that is sadly lacking in modern films. Even lackluster movies from the decade have quite a few chuckles, and the funniest films from each year are still regarded as the pinnacle of humor. Though funniness is subjective, some ’90s comedies are undeniable.

1990 – Home Alone

Though Home Alone is also regarded as one of the best Christmas movies, it’s certainly the funniest movie of 1990. A precocious kid is accidentally left home alone when his family goes on vacation, and he must stop two bumbling robbers. The film made Macaulay Culkin a star, and continued writer John Hughes’ hot streak into a new decade.

The early years of the ’90s were almost indistinguishable from the ’80s, and Home Alone very much feels like it could have been made in the previous decade. The humor is multifaceted, with an abundance of slapstick comedy punctuating the heartfelt laughs of the family-friendly film. Considering how irreverent the ’90s would become, Home Alone is unique in its decade.

1991 – L.A. Story

Comedy cratered somewhat in 1991, but L.A. Story deserves a nod as an underrated classic. Steve Martin stars as a weatherman who searches for love using communications from street signs. One of the few films to truly nail the magical realism genre in cinema, L.A. Story is a far cry from Martin’s usual humor.

It may not be uproarious, but it’s charming and clever, and the comedy comes from its strong performances and unusual scenario. It fits firmly in the romantic comedy genre, but it has enough other details to keep from being completely pigeonholed. L.A. Story is a ’90s hidden gem that deserves to be rediscovered.

1992 – My Cousin Vinny

Undoubtedly one of the best mainstream comedies of the 1990s, My Cousin Vinny is everything great about the decade’s cinema. When two young men are falsely accused of murder in a small Southern town, the titular character arrives to defend them in court. The culture clash is the heart of the humor, but the film’s characters are rich and hilarious.

Though Joe Pesci carries the film as the outlandish city-slicker, Vinny, Marisa Tomei steals the show in a role that won her an Academy Award. The brilliance of the film is that it borrows the legal drama formula, but punctuates it with abundant humor. It’s endlessly quotable and endlessly rewatchable, and it’s held up better than most classic ’90s comedies.

1993 – Groundhog Day

The cinematic mainstream was shaken up after 1993, and Groundhog Day was one of the last great movies of the ’80s hangover. A cynical weatherman travels to Punxsutawney, Pennsylvania for the annual Groundhog Day celebration, only to find himself trapped in a time loop. Not only does the film perfect the time loop concept, but it’s equally hilarious and heartwarming.

Billy Murray is at his best when playing slightly unlikable heroes like Phil Connors. Instead of simply relying on great jokes, Groundhog Day explores its concept to the fullest. It asks poignant questions about life, but it does so without sacrificing any humor. It isn’t just the funniest movie of 1993, it’s one of the best in general.

1994 – Clerks

Director Kevin Smith made Clerks for less than $50 thousand (via Vice), and it put mainstream comedy movies to shame in 1994. A down-and-out convenience store clerk spends one eventful day at his job, usually slacking off and doing everything but working. With its slice-of-life approach and irreverent characters, Clerks embodies the ’90s slacker mentality.

Clerks is made with an indie aesthetic, but it’s packed with wall-to-wall humor that compensates for its technical flaws. It helped launch Smith’s career, though the director would struggle to top his debut opus. Few comedies are as relatable as Clerks, and its lack of Hollywood gloss makes it all the more endearing.

1995 – Friday

Image via Warner Bros.

Black cinema took huge strides in the 1990s, and major hits like Friday led the way. The film concerns two friends, one of whom has just been fired, who spend one chaotic Friday in their Los Angeles neighborhood. In an era of dour depictions of Black life in the movies, Friday has a hilarious and celebratory tone.

Chris Tucker and Ice Cube were a match made in comedy heaven, and the film had a tremendous impact on popular culture. At its heart, there’s a sense of fun to the film that can only be found in the stoner comedy subgenre, and Friday is one of its best offerings. It spawned sequels, but they aren’t as good.

1996 – Happy Gilmore

Adam Sandler was one of the biggest comedy stars of the 1990s, and Happy Gilmore is arguably the best film from his heyday. Sandler stars as an ex-hockey player with anger issues who takes up golf in order to save his grandma’s home. Complete with Sandler’s signature low-brow humor, Happy Gilmore is also an excellent sports comedy.

The reason Happy Gilmore works so much better than many later Sandler comedies is because there’s a strong story at its heart. It also helps that the movie is downright hilarious, with a wide array of physical comedy and more subversive jokes too. There was stiff competition in the mid 1990s, but Happy Gilmore stands unmatched.

1997 – Austin Power: International Man Of Mystery

It would be simplistic to describe Austin Powers: International Man of Mystery as just a spoof of James Bond, it’s actually much more. Mike Myers plays the titular superspy, who travels from the ’60s to the modern day to stop his nemesis. Its parody is nearly flawless, but so much of the humor comes from Austin and his fish-out-of-water antics.

The sequels wore the jokes thin, but the first film hit it out of the park every time. There’s an unabashed goofiness to Austin Powers that is endlessly endearing, and it can be enjoyed over and over again. It’s a time capsule to the late ’90s, but in a rare instance, that isn’t a bad thing.

1998 – The Big Lebowski

The Coen brothers spent the 1990s making some of the decade’s most subversive films, but The Big Lebowski was one of the funniest. A stoner is mistaken for a millionaire, and finds himself on a dangerous quest to recover his stolen goods. Aping the structure of a detective story, the gumshoe is replaced by Jeff Bridges’ brilliant Dude.

Philosophical and yet intentionally dimwitted, The Big Lebowski is as funny as it is clever and engaging. The Coens inject the film with plenty of cinematic highlights, but it also stands as a sidesplitting comedy. The Dude has become a recognizable icon, and the film reveals more and more jokes with each successive viewing.

1999 – Office Space

A lot was made about the unfulfilling nature of white collar work in the 1990s, but no film made the point as succinctly as Office Space. A burned out office employee and his co-workers rebel against their company’s rigid structure. Creator Mike Judge clearly understood the pain of the movie’s characters, and there’s a cathartic tone to Office Space.

Being relatable is key to excellent comedy, and every viewer can take something from Office Space. It manages to poke fun at modern office culture without ever getting too narrow in its focus. Many of the jokes have become ingrained in the popular lexicon, and it’s still the definitive comedy movie about work in general.