The 20 Biggest Comedy Turkeys

20 Ishtar (1987)

Why is Ishtar, one of the most mocked flops of the 1980s, so low on this list? Because, in time, its reputation may fully come around. Celebrated writer-director Elaine May, responsible for smart, funny, edgy 1970s films like The Heartbreak Kid and Mikey and Nicky, concocted a story about a spectacularly awful songwriting duo (Dustin Hoffman and Warren Beatty) who accept a gig at a Moroccan hotel, with tons of wacky misadventures occurring. Beset with cost overruns and stories of on-set fights, Ishtar was panned by critics and bombed at the box office — the movie’s title was the name of the fictional Middle Eastern country where the action takes place, but it soon became a shorthand for any future star-driven film fiasco. 

Funny thing, though: The critical assessment has started to flip, with many now championing Ishtar as a brilliant comedy that everyone missed the boat on. “Ishtar is a very good, not very big, comedy, made by a brilliant woman,” Beatty insisted in 1991. “And I think it’s funny.” A new generation of filmmakers and journalists agree — this movie’s turkey status may be revoked soon. 

19 The Bonfire of the Vanities (1990)

Right before Tom Hanks won back-to-back Best Actor Oscars, he signed on to this highly-anticipated adaptation of Tom Wolfe’s decade-defining novel, playing Sherman McCoy, a so-called Master of the Universe who works on Wall Street during the greed-is-good 1980s. The Bonfire of the Vanities was meant to be a biting commentary on race, greed, immorality and politics, but director Brian De Palma couldn’t make the satire sting. Blame the miscasting: Hanks was all wrong, at that stage of his career, as a soulless weasel; and Bruce Willis struggled as Peter Fallow, a slimy journalist who makes his name exposing a huge scandal Sherman is trying to keep secret. The movie tanked at the Christmas box office and is now held up as one of the prime examples of How Not to Turn An Acclaimed Book Into A Movie.

18 The Adventures of Rocky and Bullwinkle (2000)

It’s important to remember that reanimating dusty old intellectual property isn’t some new Hollywood trend. At the end of last century, Universal Pictures decided to bring Rocky, Bullwinkle, Boris, Natasha and Fearless Leader to the big screen. That idea sounded pretty great — if you were familiar with the Rocky and Bullwinkle cartoon from decades earlier. Unfortunately, not a lot of folks were, which helped contribute to this live-action film’s financial failure. The other problem, of course, was that The Adventures of Rocky and Bullwinkle couldn’t capture the nutty comic spirit of the old show, even though it was very enjoyable to see Robert De Niro try his hand at playing Fearless Leader. Fun fact: The script was written by Kenneth Lonergan, who went on to win an Oscar for a very different kind of film, Manchester by the Sea. 

17 Land of the Lost (2009)

Before Land of the Lost, Will Ferrell had starred in some smaller comedies that were surreal and goofy — like Semi-Pro — that weren’t huge hits. But this adaptation of the 1970s TV series was something different — a summer tentpole that could have launched a franchise — and its commercial and critical failure represented the biggest faceplant of the former Saturday Night Live funnyman’s film career. 

Sort of like a funnier Jurassic Park, the movie saw Ferrell playing a paleontologist who gets zapped into the land of dinosaurs alongside Danny McBride and Anna Friel. The big-budget picture stranded the Anchorman star in a world of bland special effects, and it didn’t help matters that Land of the Lost opened around the same time as The Hangover, which crushed it at the box office. 

“People saw that and that’s what they wanted,” co-writer Chris Henchy said later of the Bradley Cooper comedy. “Land of the Lost just wasn’t that. I think we got stuck a little bit in between pivoting to make it a little more family-friendly at the last minute when we probably should have leaned more (into the adult side). There’s a million what-ifs.” 

16 Father’s Day (1997)

In the mid-to-late 1990s, longtime friends Billy Crystal and Robin Williams ended up being in a few films together: Hamlet, Deconstructing Harry. But they were only supporting players in those movies — they starred in Father’s Day, a forgotten Ivan Reitman nothingburger written by the usually-reliable Lowell Ganz and Babaloo Mandel, which absolutely tanked. They play former lovers of the same woman (Nastassja Kinski) whose son just ran away from home. The twist: The son is either Crystal’s or Williams’, prompting the two men to go in search of him, and to find out who’s the father. Based on the hit French comedy Les Compères, Father’s Day was neither touching nor funny, magically turning two talented comics into utterly uninteresting dolts. 

15 1941 (1979)

Steven Spielberg’s World War II comedy has its supporters, but it’s probably telling that the two-time Oscar-winner has largely stayed away from making funny films since. Featuring a starry cast — Dan Aykroyd! Ned Beatty! John Belushi! John Candy! — 1941 was the movie that ended Spielberg’s hit streak, proving that the man behind Jaws and Close Encounters of the Third Kind could produce a dud. While hardly a commercial disaster — the movie actually turned a profit — this send-up of war films and disaster flicks didn’t play to this distinguished director’s great strengths, despite some impressive set pieces. Don’t feel too bad for the guy, though: Spielberg rebounded with Raiders of the Lost Ark and E.T. the Extra-Terrestrial right after.

14 How Do You Know (2010)

When he turned to filmmaking, Taxi creator James L. Brooks had a lot of success right out of the gate: Terms of Endearment won Best Picture, and Broadcast News is considered one of the great comedies of the 1980s. But he struggled in subsequent years, with I’ll Do Anything and Spanglish failing at the box office. But none of those disappointments compared to How Do You Know, a stunningly stunted romantic comedy starring Reese Witherspoon as a softball player courted by both Paul Rudd’s executive and Owen Wilson’s big-league pitcher. Brooks’ skill at combining laughs and poignancy abandoned him here, and the movie was a financial disaster, costing around $120 million because of the stars’ big paychecks. (Jack Nicholson, in what may be his final film role, was uncharacteristically awful in a small role.) Forget this movie ever existed and go back to Brooks’ first two films, which are classics.  

13 What Planet Are You From? (2000)

After the zeitgeist-y brilliance of The Larry Sanders Show, what would Garry Shandling do next? He tried his hand at films, co-writing and starring in this comedy about an alien (Shandling) who comes to Earth, looking for a human mate. As detailed in Judd Apatow’s compassionate documentary The Zen Diaries of Garry Shandling, What Planet Are You From? was a train wreck from the start, with Shandling feuding with Oscar-winning director Mike Nichols on set. Shandling received terrible reviews, and the movie stiffed commercially, perhaps proving that as much of a genius as he was, maybe he didn’t have the chops to be a bona fide movie star. 

12 Dracula: Dead and Loving It (1995)

Some filmmakers go out with a bang, their final movie being one of their definitive statements and a confirmation of their artistry. Alas, then there are folks like Mel Brooks, an Oscar-winner responsible for turning outrageous humor and envelope-pushing commentary into cinematic gold. But few had kind things to say about Dracula: Dead and Loving It, which to date is his last film. Starring Leslie Nielsen, who was far removed from the deadpan greatness of Airplane! and The Naked Gun, this forgettable spoof of vampire movies felt like Brooks running out of ideas. Maybe Brooks thought so, too: Soon after, he stepped away from movies, won a ton of Tonys for his Broadway version of The Producers, and happily enjoyed his place on the Mount Olympus of comedy.

11 R.I.P.D. (2013)

If you want proof of how great Men in Black is, watch R.I.P.D., which works with similar subject matter but misfires on every level. Like that Will Smith hit, this was based on a comic book, which was adapted into an effects-heavy action-comedy in which a wisecracking younger guy (Ryan Reynolds) partners with a gruff old pro (Jeff Bridges) — except, instead of aliens, they’re going after evil spirits. Loud, unfunny and stupid, R.I.P.D. lumbered in its attempt to be hip and witty, demonstrating just how deceptively effortless Men in Black seemed in comparison. The big-budget summer release tanked at the box office, seemingly another nail in the coffin of Reynolds’ movie-star aspirations. Three years later, he’d turn it around with Deadpool.

10 Town & Country (2001)

In the early 21st century, director Peter Chelsom made grown-up rom-coms like Serendipity and Shall We Dance? Around that same time, his Town & Country came out as well, although Chelsom joked, “Town & Country was a disaster movie, though, not a romantic comedy.” 

He’s referring to the nightmare production, which started in 1998 and dragged on for a couple years, with shooting having to be paused for months so that actors could leave to be in other films they were contractually obligated to do. Plus, Chelsom battled with star Warren Beatty, who played an architect going through all sorts of romantic travails. As the film’s cinematographer William Fraker later described it, “Peter Chelsom was a great guy, really understands cinema, but Warren was off on a track. … I don’t know what was going on with him on that picture. There were major discussions and problems. They just didn’t get along at all.” 

The budget ballooned to around $100 million, and by the time Town & Country came out, everyone smelled a flop, which it turned out to be. Beatty wouldn’t appear in another movie until he directed 2016’s Rules Don’t Apply, which was also a commercial failure.

9 Nothing But Trouble (1991)

To date, Dan Aykroyd has only directed one film. That film was Nothing But Trouble, which neither him nor its stars probably wants to remember. Chevy Chase plays a financier trying to impress pretty lawyer Demi Moore, asking her if she’d like to accompany him on a trip to Atlantic City. But after getting pulled over for a minor moving violation by John Candy’s cop, they find themselves trapped in a freaky small town on the run for their lives. Aykroyd, who also wrote the script and has a small part as a crotchety judge, said of Nothing But Trouble in 2021, “I think it is a good, serviceable comedy. I’ll say that much about it.” Critics and audiences wouldn’t say that — but, hey, at least we got this good Digital Underground song out of it.

8 Frozen Assets (1992)

Over the years, Gene Siskel and Roger Ebert panned a lot of movies on their program. But they perhaps never eviscerated a film so brutally as they did Frozen Assets, a forgotten turkey about a sperm bank, which everybody knows is the most hilarious place to set a comedy. Corbin Bernsen plays an L.A. bank executive who gets an exciting new job in Oregon — except, whoopsie, it’s a sperm bank, not a regular bank! Shelley Long works at the sperm bank, and the two of them meet-cute as they try to keep the place from going out of business. (Spoiler alert: Their plan involves sperm.) If you’ve never seen Siskel and Ebert rip on Frozen Assets, it’s way funnier than the actual movie.

7 Stop! Or My Mom Will Shoot (1992)

In Rocky mode, Sylvester Stallone can be quite funny and charming. But put him in a straight comedy, and things get dicier. Rhinestone and Oscar both failed to show off his comic chops — and it wasn’t like audiences were clamoring to see him in those movies — but the nadir was Stop! Or My Mom Will Shoot, which came out a few years after Indiana Jones and the Last Crusade, a far better version of the “Hey, let’s pair an action star with someone who could be their parent!” Stallone is a badass cop, and Estelle Getty is his nosy mother: Watch the hilarity ensue! Sadly, no hilarity ensued, and although Stop! actually wasn’t a total commercial fiasco, it didn’t turn a profit and the reviews were brutal. 

Stallone later revealed why he signed up for this dumb film in the first place: “I had heard Schwarzenegger was going to do that movie and I said, ‘I’m going to beat him to it.’ I think he set me up.” (Sure enough, Schwarzenegger confirmed that he’d tricked his rival into picking that dog.)

6 Gigli (2003)

Now that Ben Affleck and Jennifer Lopez are back together, it’ll be interesting to see if their most notorious bomb will receive a reevaluation. Released when the public had grown tired of the overexposed couple, Gigli was perhaps destined to be reviled, but even that cultural backlash doesn’t entirely account for the bad reviews that greeted this wan rom-com. What also didn’t help matters was that Affleck (as a low-ranking mobster) and Lopez (as the woman assigned to make sure he executes his latest assignment) seemed to have very little chemistry. 

5 Hudson Hawk (1991)

In his prime, Bruce Willis was a wonderfully sarcastic action hero — a likable everyman always ready with a wisecrack. But working with the wrong material, he could be susceptible to excessive smirking. That unfortunate quality was particularly on display in Hudson Hawk, a zany action-comedy, directed by Michael Lehmann of Heathers fame. Here, Willis plays the titular thief, who gets involved in a scheme to steal some Da Vinci paintings. 

You can practically hear the flop sweat coming off a talented cast, which includes Danny Aiello, Andie MacDowell, Richard E. Grant and Sandra Bernhard, as they try to make these slapstick shenanigans funny. Willis later tried to defend Hudson Hawk, saying that the movie’s fans “dig the fact that it was making fun of itself, that it was satire, and I don’t think anybody got that when it came out.” The problem was: Lots of viewers were making fun of it, too. 

4 Wild Wild West (1999)

He was the king of Independence Day at the multiplex. But no one wears the crown forever. After appearing bulletproof thanks to Independence Day and Men in Black, Will Smith reunited with Men in Black director Barry Sonnenfeld for this big-screen adaptation of the 1960s TV series. Instead of Tommy Lee Jones, this time Smith palled around with another Oscar-winner, Kevin Kline. On paper, Wild Wild West looked like a winner. But nobody watches movies on paper. This strained, unfunny would-be-blockbuster dragged where Smith’s earlier hits had soared. 

For a long time afterward, Smith would apologize to his fans for picking this project over The Matrix. 

3 The Adventures of Pluto Nash (2002)

Eddie Murphy’s 21st-century duds tend to all run together in the mind — which came out first, Meet Dave or Imagine That? — but The Adventures of Pluto Nash was the beginning of the fall. He played Pluto Nash who, in the future, runs a club on the moon, fighting with mobsters who want the spot for themselves. Director Ron Underwood had previously made charming comedies like Tremors and City Slickers, but he couldn’t do anything to save this big-budget stinker. As for Murphy, the laziness that had started to creep in once his films became family-friendly was in full effect here. It was rare we’d get a Dreamgirls or My Name Is Dolemite after this.

2 The Love Guru (2008)

Mike Myers’ Midas touch was already starting to fade — 2003’s The Cat in the Hat underperformed, failing to be the blockbuster that Jim Carrey’s big-screen How the Grinch Stole Christmas had been a few years earlier — but The Love Guru was where things started getting dire. Playing a guru hired to help a struggling hockey team get its mojo back, Myers was back in the realm of wacky accents and silly shtick, but unlike Austin Powers, nothing here was especially funny, leading to poisonous reviews and very little audience interest. 

The wretched response to The Love Guru inspired Myers to take a break from the limelight for a while — his next major role wouldn’t be until 2022’s The Pentaverate, which wasn’t any kind of triumphant comeback for the former comedy superstar.

1 Leonard Part 6 (1987)

It’s hard to articulate how massive a star Bill Cosby was in 1987. The Cosby Show was a phenomenon, and the comedian-actor was among the most beloved entertainers in the world. (How things have changed.) That’s what made it even more inexplicable that, at the height of his power, he decided to do Leonard Part 6, in which he played Leonard, a former spy who must come out of retirement to save the world. The joke of the title was that, unbeknownst to us, there were already five previous Leonard films — one of the movie’s many jokes that is not, in fact, funny. 

Cosby produced Leonard Part 6 and conceived the original story, which was shot by cinematographer Jan de Bont, who went on to direct Speed and Twister. “He saw the movie one way, and everybody else saw it different ways,” de Bont said later of Cosby. “You can’t do that; complete disagreement about the focus of a movie is totally destructive. … (I)t became a very depressing thing to work on.’” 

Not as depressing as watching it.