10 of the Best Comedy Movies From the 1990s

The ’90s was a amazing decade for comedy, introducing several stars into the mix on both the acting and directing front while giving us some true comedy classics. In fact, sometimes the comedies coming out of the ’90s can feel like the last breath of a certain kind of comedy film that dominated the ’70s and ’80s. Now that the decade is over 25 years behind us, let’s take a look back at 10 the best comedy movies from the 1990s. And for the purpose of this list, we’ll be taking a closer look at the “pure-breeds” — films like Fargo, The Player, or Being John Malkovich are extremely funny, but we’ll save them for another day.

1. Groundhog Day (1993)

Groundhog Day

Groundhog Day | Source: Columbia Pictures

It’s hard to argue that the ’80s wasn’t Bill Murray’s time to shine, but he also quietly, and not so quietly, made his mark on the ’90s — the best of which was Groundhog Day. The film tells the story of bitter and self-centered TV weatherman Phil Connors who, after covering the annual Groundhog Day event, finds himself in a time loop in which he perpetually relives February 2nd.

What makes the film interesting is that the late, great writer/director Harold Ramis doesn’t shy away from the implications of this situation as Phil indulges in hedonism and petty crime before the endless nature of the cycle leads to depression and suicides — the latter of which does nothing to break the cycle. Another fascinating aspect of this film that has come about in recent years is just how long Phil is stuck in the loop. According to Ramis it makes sense that he was stuck in the loop for at least 30 years making the events in the film even darker than would appear on the surface.

2. Dumb & Dumber (1994)

Dumb & Dumber

Dumb & Dumber | Source: New Line Cinema

Dumb & Dumber is a titan among ’90s comedies, emblematic of a shift in the genre because of actors like Jim Carrey and the influence of directors Peter and Bobby Farrelly. The film follows two friends who go on a journey to return a suitcase full of money and get into every conceivable ridiculous situation that could possibly arise when they have no idea the danger they’ve put themselves in.

While it can be argued that Dumb & Dumber might not be the best Farrelly Brothers comedy from the ’90s (we’ll get to that later), there’s no doubt that the film is easily their most iconic. Not only does the film continue to highlight Carrey as one of the greatest comedic actors of his generation, it is also a revelation seeing Jeff Daniels in a comedic role who matches Carrey scene after scene. Famously, New Line Cinema fought over Daniels’s inclusion in the film (he had been previously associated with drama) leading Daniels to eventually take a huge pay cut. Dumb & Dumber lives and breathes because of the brilliance of its two leads, and it’s hard to think of a movie that better defines what we think of as a ’90s comedy.

3. Office Space (1999)

Office Space

Office Space | Source: 20th Century Fox

Office Space just barely squeaks into the ’90s arena, but if we’re talking about comedies that remain relevant it’s impossible to leave it off the list. The film was Mike Judge’s first live-action film and tells the story of a group of software employees whose soul-crushing existence leads them to try to steal money from their job via a scheme straight out of Superman 3.

While Office Space wasn’t a success at the box office, it has developed a cult following over the years and has never been more popular — a trend also overseen by Judge’s 2006 film Idiocracy. The biting satire of the film along with its depiction of crushing work-life feels just as relevant today as ever making for a watch that isn’t likely to stop connecting with audiences anytime soon. And the joy of seeing a broken printer destroyed with a bat and fists is as cathartic as it gets.

4. Clueless (1995)

Clueless

Clueless | Source: Paramount

Clueless is another ’90s comedy cornerstone, and one that is completely and utterly a product of its time — and that’s a good thing. The film tells the story of Cher (Alicia Silverstone), a shallow and popular high school student in Beverly Hills who finds herself running into issues when she attempts to transform a new student into someone like her.

Directed by Amy Heckerling (Fast Times At Ridgemont High), Clueless is above all odds a loose adaptation of Jane Austen’s Emma that shapes the classic novel into a comedy that comments on teen films, Beverly Hills culture, and ’90s culture at large. Unlike many films that feel dated because they reflect the times to a fault, the nature of Clueless as a film makes it feel almost like a period-piece in which the style and feel of the decade is key to the film’s success.

5. The Big Lebowski (1998)

Jeff Bridges in The Big Lebowski

The Big Lebowski | Source: Universal Pictures

The Coen Brothers have made a habit of alternating between drama and comedy and everything in-between, but The Big Lebowski stands out as the duo’s best comedy film to date and might be among their best overall. The genre-busting neo-noir crime comedy tells the story of Jeffrey “The Dude” Lebowski (Jeff Bridges) who finds himself embroiled in a classic noir mystery despite the fact that he’s the last person positioned to deal with it.

The Big Lebowski is loosely inspired by the pulp crime writing of Raymond Chandler that has informed many noir and neo-noir films before it, but here we have the opportunity of seeing the absurd situations unfold when a person least equipped to handle the heat finds himself at the center of it all. Interestingly enough, the film earned mixed reviews upon release due at least in some part to the the Coen Brothers releasing the critically acclaimed Fargo only two years before. But its status as a cult-classic only increased over the years until it’s now reached a point where it can comfortably be called a classic.

6. Clerks (1994)

Clerks

Clerks | Source: Miramax

Kevin Smith’s Clerks is one of the poster-children of the independent film movement of the ’90s. Shot on a shoestring budget in black-and-white, Clerks gives us a glimpse into a day in the life of two slacker store clerks, Dante and Jeff, as they talk about relationships, Return of the Jedi, and the fact that Dante “wasn’t even supposed to be here today.”

While Smith’s track-record in the years since has been mixed, his first film Clerks is still the best — and funniest. The film was shot for a measly $27,575 using funds from selling an extensive comic book collection, maxing out credit cards, and a bunch of other risky methods that have become the stuff of legends when it comes to the indy filmmakers of the ’90s. And in a prime example of using what you have at your disposal, or alternatively life imitating art, Smith shot the film at the two stores he worked at at the time. It’s not just a classic of its time — it’s a classic.

7. Home Alone (1990)

Macaulay Culkin in Home Alone

Home Alone | Source: Fox

The ’90s got off to a great start when Home Alone crashed onto the scene. From writer/producer John Hughes and directed by Chris Columbus, Home Alone tells the story of Kevin, an 8-year-old beyond his years, who is accidentally left at home while his family goes on vacation. While this is at first a dream come true for Kevin, he soon finds himself at war with two burglars whom he must defend the house from.

You can call Home Alone whatever you want: a Christmas classic, a comedy classic, or a kids classic. Not only did the film jumpstart Macaulay Culkin’s film career, it gave us the iconic physical-comedy performances of Joe Pesci and Daniel Stern. The film was also unstoppable at the box office earning $285 million in the U.S. alone, which today would put it somewhere close to $600 million when adjusted for inflation. But the appeal for kids in particular is obvious: This is a film about kids and their mastery over adults in a world where they usually have little power. It’s pure catharsis.

8. There’s Something About Mary (1998)

There's Something About Mary

There’s Something About Mary | Source: 20th Century Fox

Is the Farrelly Brothers’ There’s Something About Mary better than Dumb & Dumber? Possibly, but who cares when we have both of them to enjoy. Featuring an all-star cast with Cameron Diaz, Ben Stiller, Matt Dillon, and a host of other memorable supporting actors, There’s Something About Mary tells the story of Ted (Stiller) and his journey to win over Mary (Diaz), the girl he missed out on in high school.

The first thing to note when talking about the Farrelly Brothers and There’s Something About Mary is that the comedy pair was clearly on another level in the ’90s. In one decade they managed to deliver three classic comedies, and the one film that hasn’t been mentioned on this list — Kingpin — just as easily could have been.

But returning to There’s Something About Mary, this is a film with a barrage of iconic moments: the hair gel, an accident with a zipper, a killer hitchhiker with the brilliant idea of seven-minute-abs. What also might make the film the best of the bunch is that it feels the most cohesive when it comes to the core story and the great comedic bits that surround it. Whether you go with There’s Something About Mary or Dumb & Dumber, or even Kingpin, as the best Farrelly Brothers film, no one’s going to argue.

9. Rushmore (1998)

Rushmore

Rushmore | Source: Buena Vista Pictures

Rushmore follows teenager Max Fischer (Jason Schwartzman) as his friendship with industrialist Herman Blume (Bill Murray) is put to the test when they both fall in love with an elementary school teacher named Rosemary Cross (Olivia Williams). What begins as an infatuation for Max soon turns to obsession and, later, treachery when it comes to Herman.

Wes Anderson’s track-record as a filmmaker is about as consistent as they come. Starting off with the low-budget Bottle Rocket in 1996, his 2014 film The Grand Budapest Hotel represented his biggest box office success to date while earning universal critical acclaim. But Rushmore is still his best film filled with some of the funniest moments of his career. Not only did it represent the first role for Schwartzman, it was the film that put Murray on the map as an actor with the range to take on more dramatic roles — something that’s a good thing or a bad thing depending on who you ask.

10. My Cousin Vinny (1995)

My Cousin Vinny

My Cousin Vinny | Source: 20th Century Fox

My Cousin Vinny stars Joe Pesci as the titular Vinny — a personal injury lawyer from Brooklyn who has recently passed the bar following his sixth attempt. When Vinny’s cousin and his friend are implicated for a murder in Alabama they didn’t commit, he becomes the only chance they have to be exonerated despite the fact that he’s never even been in a court.

My Cousin Vinny often gets lost in the ’90s comedy shuffle, sometimes better known as the film in which Tomei improbably won an Academy Award for Best Supporting Actress. But the film is among the best of the decade, comedy or otherwise. The source of the film’s humor comes from the clashes between the brash, New York working class characters in the film and the conservative, reserved Southerners in Alabama. One of Pesci’s best roles in a distinguished career, the film has also been heralded as an authentic depiction of courtrooms and trial strategy in a genre that often comes across as fake.

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