10 Funniest Comedy Movies That Flopped at the Box Office

Considering the star-studded casts of these comedy movies, there’s no telling why audiences slept on their respective releases when they were first released in theaters. On top of featuring name value, the movies were also made by talented crew members, from writers to directors and everyone in between.

Several of these movies are held in high regard today, having garnered cult classic status many years down the line. Justifiably so, even if they should have raked in millions at the worldwide box office to pay the cast and crew for the fan-favorite work they produced. Each movie deserves more love today — hopefully, this list will do them justice. These are the funniest comedies that flopped at the box office, ranked.

10 Wet Hot American Summer (2001)

Box Office Total: $295,206 – Budget: $1.8 Million

Featuring an ensemble cast, Wet Hot American Summer (2001) is among the first credits from names like Paul Rudd, Amy Poehler, and Elizabeth Banks. It even marks the on-screen debut of Bradley Cooper, and until its final frame, Wet Hot American Summer remains one of the funniest movies throughout each of their careers.

Hindsight Is 20/20

With a cult following, this satirical comedy is held in high regard today by fans for its respectable spoofing of teen summer camp films. It takes place on the last day of Camp Firewood, a fictional program wherein the aforementioned stars play counselors and directors. Though by no means revered upon release, Wet Hot American Summer still shouldn’t have come up so drastically short re: revenue. In hindsight, most audiences would agree. Rent on AppleTV.

9 I Heart Huckabees (2004)

Box Office Total: $20.1 Million – Budget: $20 Million

With David O. Russell as the writer-director, I Heart Huckabees (2004) showcases how that particular filmmaker always comes up short with his comedies. At least, with regard to box office success. His ’90s projects like Flirting With Disaster (1996) are still wildly underrated today, though not quite to the extent of I Heart Huckabees, starring Jason Schwartzman as an environmentalist.

An Off-the-Wall Plot

He hires a pair of detectives, played by Dustin Hoffman and Lily Tomlin, only for the source of his investigation to turn around and hire the same detectives for his own purposes. Like most David O. Russell movies, it’s well-paced until its final frame, and without a doubt, I Heart Huckabees will elicit laughs along the way. Even if the movie theaters were mostly defined by silence. Rent on AppleTV.

8 Mystery Men (1999)

Box Office Total: $33.5 Million – Budget: $68 Million

A spoof of the superhero genre, Mystery Men (1999) would likely clean up at the worldwide box office had it been released in theaters today. Given the current landscape of comic book adaptations, audiences would’ve lined up en masse at their local movie theaters to see Ben Stiller, Janeane Garofalo, and William H. Macy poke fun at the once-great realm of superhero movies.

Accruing Just Half of its Budget

At the worldwide box office, Kinka Usher’s story about amateur superheroes accrued just $33.5 million against its $68 million budget. It bombed, in other words, in spite of positive reviews from critics and endless laughs from audiences who went to see it.

An uproarious adventure the whole way through, Mystery Men is worth the watch if not for the efforts of its cast alone. Ben Stiller provides one of his most animated performances, and Macy is right by his side with a shovel. Stream on Starz with AppleTV.

7 Tenacious D in the Pick of Destiny (2006)

Box Office Total: $13.9 Million – Budget: $19-$20 Million

Although held in high regard by film fans from a contemporary perspective, Tenacious D in the Pick of Destiny was by no means successful when it was released in 2006. And while it does get more love today, one person thrown by the wayside of its quality would have to be the director, Liam Lynch.

The Talent of its Crew

After working on School of Rock (2003) as a sound consultant, Liam Lynch reunited with funnyman Jack Black to create Pick of Destiny. They both wrote the script alongside Jack’s co-star Kyle Gass, with the plot following their characters (of the same name) as they venture forth in search of a pick that grants its users the ability to rock. It’s a hilarious journey with songs by the stars, and for all the work they put in, the crew should’ve made bank at the box office. Rent on AppleTV.

6 Hot Rod (2007)

Box Office Total: $14.4 – Budget: $25 Million

To this day, film fans exchange quotes from Hot Rod (2007), directed by Akiva Schaffer from Pam Brady’s original script. Among the biggest flops at the box office that you’ll read about today, it barely scraped together $14 million, and that’s in spite of a fairly sizable budget of $25 million. Considering the number of audiences who quote Hot Rod today, one would think it’d have been more successful.

A Star-Studded Cast

If endlessly funny dialogue wasn’t enough, Hot Rod also features a star-studded cast. It follows Andy Samberg’s protagonist Rod, a stuntperson looking to accrue money for his stepfather’s heart operation. The latter is played by Ian McShane, while other actors include Danny McBride, Bill Hader, Isla Fisher, and Sissy Spacek. They all play prominent parts in an uproarious plot that, even from a perspective of critical reception, deserves far more love today. Rent on AppleTV.

5 Idiocracy (2006)

Box Office Total: $495,303 – Budget: $2.4 Million

Over the past few years, there’s been rampant discussion about how accurately Idiocracy (2006) predicted the future. Directed by Mike Judge from a script he co-wrote alongside Ethan Cohen, this underrated comedy takes place in a dystopian United States. The year is 2505, and after a botched hibernation experiment run by the government, Luke Wilson’s protagonist Joe awakens in a shell of his former country.

Unforgettable Characters

As he traverses an America that’s completely overrun by technology, he finds the citizens so reliant on the advances of the twenty-first century that their intelligence quotients have essentially devolved to resemble those of our neanderthal counterparts.

For as memorable a setting as Mike Judge created with Idiocracy, the true beauty therein is left to be found in its characters. Everyone performs hilariously, from Maya Rudolph and Dax Shepard to Terry Crews and Justin Long — with that kind of talent, there’s no telling how Idiocracy flopped at the box office. Rent on AppleTV.

4 Black Dynamite (2009)

Box Office Total: $296,557 – Budget: $2.9 Million

The comedic genius of Michael Jai White cannot be overstated — his first foray into the cinematic world of comedy came by way of Black Dynamite (2009), a spoof of Blaxploitation films. The aforementioned writer-director (almost exclusively known before this for his stints in martial arts movies) also stars in Black Dynamite as the eponymous CIA agent.

How MJW Became a King of Comedy

More than a decade after Black Dynamite, the star of the show followed up with another world-class spoof in the form of Outlaw Johnny Black (2023). It pokes fun at the western genre, and what’s more, it marked White’s feature-film debut. He co-wrote the script for Black Dynamite alongside director Scott Sanders, and it clearly gave him valuable insight into the ins-and-outs of spoof movies. For many fans, his first will always be his funniest. Stream on Starz.

3 Office Space (1999)

Box Office Total: $12.2 – Budget: $10 Million

Although the aforementioned comedy Idiocracy gives it a valiant run for its money, Office Space (1999) is perhaps the magnum opus of writer-director Mike Judge. It’s a satirical take on the status of office culture, homing in on Ron Livingston’s character Peter. He works as a programmer at a software company, and along with Jennifer Aniston as Joanna, the cast primarily consists of actors who portray his co-workers. They all perform brilliantly.

A Certified Cult Classic

Due to the mediocre revenue it accrued, Office Space now boasts a committed cult following. The praise from critics upon release should have driven comedy fans to see this laugh riot in theaters, but alas, it barely made back its $10 million budget. Considering how funny film fans call Office Space today, those numbers are shocking in hindsight. Stream on Max.

Related: Best Richard Linklater Movies, Ranked

2 Scott Pilgrim vs. the World (2010)

Box Office Total: $49.3 Million – Budget: $60-$80 Million

Adapted from Brian Lee O’Malley’s graphic novel series, Scott Pilgrim vs. the World (2010) was directed by Edgar Wright from a script he wrote with Michael Bacall. The latter is an underrated screenwriter, also holding credits on both films in the Jump Street series. Those are two of the funniest movies of the century, and for some fans, Scott Pilgrim is even better.

An Endlessly Unique Experience

After meeting Mary Elizabeth Winstead’s character Ramona Flowers, protagonist Scott Pilgrim (played indelibly by Michael Cera) must fight through her “Seven Deadly Exes” in order to gain her love.

It’s a weird plot, with alluring visuals and intricate sound design — combining to create an atmosphere that truly resembles a comic book — rivaling the idiosyncrasies of the story itself. Considering the high regard that fans hold this comedy in, there’s no telling how it flopped upon release. Stream on Prime Video.

Related: The Best Michael Cera Movies, Ranked

1 Dazed and Confused (1993)

Box Office Total: $8.2 Million – Budget: $6.9 Million

Matthew McConaughey, Milla Jovovich, Parker Posey, Ben Affleck — if Dazed and Confused (1993) were released today with names of that star power, audiences would be lining up en masse within their local movie theaters. However, that wasn’t the case in the early 1990s. After debuting with Slacker (1990), writer-director Richard Linklater outdid himself with this essential stoner comedy, even if it bombed at the box office.

Tapping Into Nostalgia

Every name among the cast performs to perfection in this laugh-out-loud high school comedy, which chronicles several groups of friends on the first day of summer. Lots of partying, lots of hanging around, doing nothing. With well-written character dynamics and indelible lines of dialogue, Linklater crafted a hilarious comedy about high school in the seventies, and along the way, he tapped perfectly into the audience’s nostalgia. Rent on AppleTV.