The 10 Best So-Bad-They’re-Good Comedy Movies of the ’90s, Ranked

The 1990s are a treasure trove of some of the best and most popular comedy movies ever made, like Ace Ventura: Pet Detective, Office Space, Austin Powers: International Man of Mystery, and Wayne’s World. Some of the best comedy movies from that decade weren’t well received when they were initially released, but went on to achieve cult status.

The decade features lots of movies starring Saturday Night Live cast members, often reprising popular character roles from the sketch comedy series. This was the decade that made stars of comedy actors like Jim Carrey, Adam Sandler, and Mike Myers, and brought forth some of the most memorable comedies in history. It would be overreaching to christen the following as such, but they’re undeniably so-bad-it’s-good fun.

10 ‘Robin Hood: Men in Tights’ (1993)

Directed by Mel Brooks

Everyone knew Cary Elwes from his iconic performance as Westley in The Princess Bride. But several years later, he starred in this adventure comedy movie that serves as a clever parody of the story of Robin Hood. He’s Robin of Loxley who, upon returning home after being captured and imprisoned, discovers that unbeknownst to King Richard (Patrick Stewart) who is away fighting a war, his spoiled son Prince John (Richard Lewis) has been severely abusing his power. Robin takes it upon himself to take down the Prince, but also has to save himself from an assassination attempt.

Filled with hilarious takes on the classic story, from Maid Marian of Bagelle (Amy Yasbeck) in search for the man who holds the key to her chastity belt to Rabbi Tuckman (Mel Brooks) who offers bargain circumcisions, the entire movie is pure, silly fun. The movie also notably marks comedian Dave Chappelle’s film debut as Ahchoo, son of Asneeze (Isaac Hayes) and features a rare cameo from creator Brooks himself. Robin Hood: Men in Tights had a lot of competition in the juvenile humor category during this decade, but it deserves to be cited among the best.

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9 ‘She’s All That’ (1999)

Directed by Robert Iscove

The premise has been played out and the concept wouldn’t fit with today’s politically correct climate and the general public disdain for stereotypes. But She’s All That remains a gem of a teen romantic comedy that, when taken for what it’s worth, is both funny and sweet. It begins when Zack (Freddie Prinze Jr.), the popular boy in high school, engages in a friendly bet with his best friend Dean (the late Paul Walker). After being cheated on by his girlfriend, Zack claims he can get any girl in the school he wants. Dean, eager to have some fun, points out the awkward, nerdy girl Laney (Rachael Leigh Cook). Fueled by his desire to win the bet, Zack starts to flirt with Laney, slowly bringing her out of her shell and making the young woman feel like she never has.

Of course, as the story would go, Laney discovers the truth just as Zack realizes he actually has genuine feelings for her. The iconic scene when Laney walks down the stairs following a seemingly transformational makeover (it’s amazing what contacts, make-up, and a pretty dress and heels can do) has become a classic among kids of the ‘90s. Of course, the lesson that a girl (or guy) needs to change the way they look to be loved isn’t one that should be spread. But as an innocent and sweet teen rom-com taken for its surface entertainment value, She’s All That achieves what it sets out to do.

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8 ‘Tommy Boy’ (1995)

Directed by Peter Segal

The late Chris Farley is one of many SNL cast members who starred in comedy movies during the ‘90s. Tommy Boy wasn’t among the best reviewed by critics but one that audiences loved. It features Farley’s signature spastic physical comedy alongside David Spade (also a former SNL cast member) and his more subdued, sarcastic style. A buddy comedy film, it’s about an immature man named Tommy (Farley) dealing with the death of his father.

That doesn’t sound exactly humorous, but the story takes Tommy on a mission to prove his worth and abilities. He promises to sell half-a-million brake pads to secure control over his father’s business. Spade plays Richard, Tommy’s father’s assistant who goes along for the ride, but doesn’t make things easy for him. At its heart, Tommy Boy has a positive premise, akin to Adam Sandler’s Big Daddy, which has become a cult classic from that decade. Since the movie had competition from much bigger movies of the time, Tommy Boy sunk to the background. But it stands out for being one of few to show not only Farley’s ability at loud and abrasive comedy, but also his softer, more vulnerable side, too.

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7 ‘A Night at the Roxbury’ (1994)

Directed by John Fortenberry

Will Ferrell has been in some of the best comedy movies of the last few decades. Many of them overshadow A Night at the Roxbury, a comedy in which he stars alongside Chris Kattan. One of the best movies to turn your brain off to, they are Steve and Doug, two brothers who love to frequent night clubs, bob their heads in unison, and awkwardly attempt to pick up women. The characters were developed as part of a recurring Saturday Night Live sketch and quickly became fan favorites, spawning this movie that sees the pair go on an adventure to try and get into one of Los Angeles’ most famous clubs called the Roxbury. Not surprisingly, the eccentric duo is constantly turned away and have made it their mission to bypass the menacing bouncer.

With an incredibly talented comedic supporting cast that includes everyone from Loni Anderson to Molly Shannon, Jennifer Coolidge, and Colin Quinn, A Night at the Roxbury centers on these silly, one-note characters. But the pathetically lovable characters remain hilarious to watch and emulate by fans.

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6 ‘Can’t Hardly Wait’ (1998)

Directed by Deborah Kaplan, Harry Elfont

There were so many teen rom-coms in the ‘90s, and Can’t Hardly Wait is one that often gets lost in the mix. But it shouldn’t. The movie has a cast of characters who all went on to achieve great success in comedy but were relative unknowns at the time, like Ethan Embry, Lauren Ambrose, Peter Facinelli, and Seth Green. Jennifer Love Hewitt, fresh off her starring role in Party of Five, leads the cast as Amanda, a young woman attending an epic high school graduation party.

While the movie is from the ‘90s, the style is set like a classic ‘80s movie, clearly drawing inspiration from the works of John Hughes. It’s a coming-of-age story about kids getting ready to move on and trying to get in their last “hurrahs” now that school is over. There are all the typical stereotypes, from the pretty girl to the awkward guy with a crush, the social outcasts, the nerds, and the bullies. Beyond the main cast, fans will notice other known actors appearing in small, in some cases even unnamed, roles, like Jaime Pressly, Donald Faison, Selma Blair, and Chris Owen.

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5 ‘Don’t Tell Mom The Babysitter’s Dead’ (1991)

Directed by Stephen Herek

Christina Applegate was still starring in the sitcom Married With Children when she appeared in this coming-of-age black comedy movie with a ridiculously unbelievable premise but totally fun story. She’s a 17-year-old named Sue who is left at home with her siblings for summer, but their mother decides to hire a babysitter to help. As tragedy (or luck) would have it, however, the elderly woman dies in her sleep, leaving Sue on her own to care for the kids. Rather than alert their mom or the authorities, they decide to enjoy their summer of freedom. But they realize too late that they dropped off the body at a local mortuary with all the spending money from their mom on her person.

Don’t Tell Mom the Babysitter’s Dead is as much a tale of growing up and maturing as it is a comedy. Applegate is a scene stealer as a teenager coming into her own, providing for the family when she realizes she has to step up. The movie isn’t as silly as the title makes it sound, which is arguably what makes it so bad. But going in knowing what to expect, it’s actually quite entertaining. In fact, it has even spawned a remake.

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4 ‘Encino Man’ (1992)

Directed by Les Mayfield

Beloved to this day for his acting talent and seemingly nice guy personality, Brendan Fraser did a lot of silly comedies in the ‘90s, but arguably none as silly as Encino Man. In this, one of his classic roles, Fraser plays a caveman who, through an earthquake, is able to pass through time where he ends up befriending an awkward teenage named Dave (Sean Astin). Together with Dave’s best friend Stoney (Pauly Shore), the pair try to communicate with the caveman they eventually name Link, teaching him out the ways of modern society.

It’s an absolute hoot to see Fraser play the cluelessly barbaric caveman who doesn’t understand modern grooming, safety, and technology. It’s a wonder Encino Man never spawned a sequel, though there was a made-for-TV spin-off called Encino Woman in 1996.

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3 ‘Home Alone 3’ (1997)

Directed by Raja Gosnell

Home Alone 3 was not nearly as good as Home Alone and Home Alone 2. It also wasn’t a great movie in general. But it is one of those movies that’s so bad, it’s also pretty good. The story, inspired by the original, is centered around a new main child character, Alex, an 8-year-old who has come into possession of a remote control car that just so happens to house a microchip a dangerous terrorist organization wants to get their hands on. They track it down and, of course, Alex must do what needs to be done to protect his house.

It’s the first in the series not to include Macaulay Culkin and it marks a departure from the franchise, making Home Alone 3 a hated Christmas movie. But when viewed as a movie on its own and not part of the iconic Christmas movie franchise, Home Alone 3 is one of those movies to watch in order to criticize but also secretly enjoy.

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2 ‘Kindergarten Cop’ (1990)

Directed by Ivan Reitman

Spawning numerous one-liners that are still spoken today by fans of the movie (and even some who don’t know of their origins), Kindergarten Cop proved that while Arnold Schwarzenegger was a bona fide action movie star, he had comedic chops, too. As is typical for his many comedy movies of that time, Schwarzenegger plays a fish-out-of-water as John, a detective who has to go undercover as a schoolteacher.

It might not be one of his best movies, but seeing the larger-than-life Schwarzenegger interacting with tiny, innocent kindergarten kids who have no filter is comedic gold. Despite the odds being stacked against him, John starts to warm to the kids and they to him, such that he starts to actually enjoy being with them. Kindergarten Cop is refreshingly funny with innocent humor and wildly entertaining dialogue, particularly from the kid cast.

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1 ‘So I Married An Axe Murderer’ (1993)

Directed by Thomas Schlamme

Mike Myers is known for so many comedy movie franchises, from Austin Powers to Wayne’s World andShrek. But one of his most overlooked titles is So I Married An Axe Murderer, a silly romantic black comedy about a commitment phobic man who meets the woman of his dreams, but then begins to suspect that she might be a serial killer. Fueled by his own penchant for finding fault in every woman he dates along with his mother’s obsession with salacious tabloid headlines and a series of coincidental events he just can’t shake, Charlie (Myers) tries to distance himself from Harriet (Nancy Travis) to comedic effect.

Charlie is sweet, kind, but as is typical of any character Myers plays, he’s also very funny. Myers also plays his surly, elderly father Stuart who speaks with a thick Scottish accent. The supporting cast that includes Anthony LaPaglia as Charlie’s best friend and cop Tony, the late Phil Hartman as a tour guide named John (but people call him Vickie), and the late Alan Arkin as Tony’s captain, meet Myers’ comedic timing. So I Married An Axe Murderer is the type of movie to watch over and over, picking up on subtle jokes each time, and banking dozens of quotes to repeat in everyday conversation.

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