The Funniest Comedy From Every Year Of The ’90s

The 1990s were a fantastic era for funny movies, with each year delivering at least one truly memorable comedy that still makes people laugh. Building on the success of 1980s comedies, the 1990s took the genre in a fresh direction, with new filmmakers bringing a bold and playful style to the screen.

While traditional comedy remained popular in the 1990s, the decade also saw a surge in independent films that truly reflected the mood of the time. These films, often low-budget, connected with Gen-X through a more relaxed, ‘slacker’ style, and weren’t afraid to tackle topics mainstream Hollywood avoided. This led to a unique situation where comedy didn’t have one single, dominant voice – it was much more diverse.

While ’90s comedies were diverse, they shared a certain wit that’s often missing in today’s films. Even the weaker movies from that decade still manage to get a few laughs, and the best ones are still considered incredibly funny. Although humor is a matter of personal taste, many ’90s comedies are simply undeniable classics.

1990 – Home Alone

While Home Alone is often listed among the greatest Christmas movies, it’s widely considered the funniest film released in 1990. The story centers on a clever young boy who’s mistakenly left behind when his family goes on vacation, and he has to outsmart a pair of clumsy burglars. The movie launched Macaulay Culkin to stardom and kept writer John Hughes’ successful run going strong into the nineties.

The beginning of the 1990s didn’t feel much different from the 1980s, and the movie Home Alone really captures that earlier feel – it could easily have been made in the previous decade. The film offers a lot of different kinds of humor, mixing silly physical comedy with genuinely heartwarming and funny family moments. When you consider how edgy and unconventional the ’90s would eventually become, Home Alone stands out as something special for its time.

1991 – L.A. Story

While comedy films generally struggled in 1991, L.A. Story stands out as a hidden gem. Steve Martin plays a weatherman looking for love, guided by quirky messages he finds on street signs. A rare success in the magical realism genre, L.A. Story is quite different from the typical Steve Martin comedy.

While not laugh-out-loud funny, this movie is delightful and smart, with its humor stemming from great acting and a unique story. It’s definitely a romantic comedy, but it offers enough originality to stand out. L.A. Story is a fantastic ’90s film that more people should see.

1992 – My Cousin Vinny

Considered one of the most enjoyable mainstream comedies of the 1990s, My Cousin Vinny really captures what made movies from that era so good. The story follows two young men wrongly accused of murder in a small town in the South, and the arrival of their eccentric cousin Vinny, who steps in to defend them in court. The humor comes from the clash between Vinny’s New York attitude and the Southern culture, but the film is also funny because of its well-developed and hilarious characters.

While Joe Pesci is fantastic as the quirky lawyer Vinny, Marisa Tomei truly shines, earning her an Oscar for the role. What makes the film so great is that it uses the familiar structure of a legal drama, but fills it with plenty of humor. It’s a movie full of memorable lines and remains highly enjoyable even today, standing the test of time better than many other comedies from the 1990s.

1993 – Groundhog Day

The movie scene changed significantly after 1993, and Groundhog Day is often considered one of the last truly great films to come out of the 1980s style. The story follows a grumpy weatherman who gets stuck reliving the same Groundhog Day over and over again in Punxsutawney, Pennsylvania. It’s a film that not only mastered the idea of time loops, but also manages to be both funny and touching.

Billy Murray shines when he plays flawed but compelling characters, like Phil Connors. The movie Groundhog Day goes beyond just being funny; it fully develops its unique premise. It thoughtfully examines life’s big questions, all while remaining hilarious. It wasn’t just the funniest film of 1993—it’s a truly great movie overall.

1994 – Clerks

Director Kevin Smith famously made Clerks for under $50,000 (according to Vice), and it was a surprisingly fresh take on comedy when it came out in 1994. The film follows a bored convenience store clerk through a typical, chaotic day, mostly filled with avoiding work. With its realistic portrayal of everyday life and quirky, unconventional characters, Clerks really captured the spirit of ’90s slacker culture.

Though made on a low budget and with a distinctly independent style, Clerks is incredibly funny, more than making up for any technical shortcomings. It was a breakout hit for director Kevin Smith, but he’s never quite matched the success of this first film. Clerks is remarkably relatable, and its raw, unpolished look is part of what makes it so charming.

1995 – Friday

Image via Warner Bros.

The 1990s were a significant period for Black films, with movies like Friday becoming major successes. The film follows two friends in Los Angeles, one recently unemployed, as they navigate a wild and funny Friday in their neighborhood. Unlike many films of the time that showed difficult aspects of Black life, Friday stood out with its joyful and comedic approach.

Chris Tucker and Ice Cube had incredible comedic chemistry, and their movie Friday really resonated with audiences. It’s a genuinely funny film, and a standout example of stoner comedies. While there were sequels, they didn’t quite live up to the original.

1996 – Happy Gilmore

Adam Sandler became a huge comedy star in the 1990s, and many consider Happy Gilmore to be his best movie from that period. The film features Sandler as a former hockey player who, despite his temper, takes up golf to try and save his grandmother’s house. Happy Gilmore is full of Sandler’s classic silly humor, but it’s also a really well-done sports comedy.

What makes Happy Gilmore so much better than many of Adam Sandler’s later movies is its solid storyline. Plus, it’s genuinely funny, combining slapstick with clever, unexpected humor. Even with a lot of other comedies coming out around the same time in the mid-90s, Happy Gilmore remains in a league of its own.

1997 – Austin Power: International Man Of Mystery

As a film buff, I’ve always loved Austin Powers: International Man of Mystery. It’s easy to think of it as just a James Bond spoof, but honestly, it’s so much more than that. Mike Myers is brilliant as Austin Powers, this super-spy who gets thrown from the groovy ’60s into the present day to take down the bad guy. The parody is spot-on, seriously, almost perfect, but what really makes it hilarious is watching Austin navigate the modern world – he’s totally a fish out of water!

While the later movies weren’t as funny, the original Austin Powers was a huge success. The film has a charmingly silly quality that makes it really likeable, and it’s a movie you can watch again and again. It perfectly captures the feel of the late 1990s, and surprisingly, that’s a good thing.

1998 – The Big Lebowski

As a huge film buff, I always think back to the Coen brothers’ amazing work in the ’90s – they really pushed boundaries with their movies. But for sheer laughs, The Big Lebowski is right up there. The plot is just brilliant: this laid-back stoner gets mixed up in a crazy situation when someone mistakes him for a rich guy, and suddenly he’s on this wild, dangerous journey to get his stuff back. It’s cleverly done, too – the movie plays with the classic detective story format, but instead of a hard-boiled detective, you’ve got Jeff Bridges as The Dude, and he’s absolutely perfect in the role.

Despite its thoughtful moments, The Big Lebowski is a hilariously entertaining film. The Coen brothers fill it with memorable scenes, but at its heart, it’s a genuinely funny comedy. The main character, The Dude, has become a cultural icon, and the movie continues to reveal new jokes and details with every rewatch.

1999 – Office Space

The feeling that many office jobs weren’t satisfying was a big topic in the 1990s, and the film Office Space captured that feeling perfectly. It tells the story of frustrated office workers who decide to fight back against their strict and unfeeling company. Creator Mike Judge seemed to really understand what it was like to be in their shoes, giving the movie a relatable and satisfying tone.

Great comedy connects with everyone, and Office Space does just that. It hilariously captures the frustrations of working in an office without being overly specific, making it universally funny. The movie’s jokes have become well-known phrases, and it remains the most iconic comedy about the working world.

2025-12-14 01:11