The 10 Worst Comedies of the 21st Century

The 10 Worst Comedies of the 21st Century

Putting together a list of this century’s worst comedies can be a difficult task because, really, who wants to remember the movies that left you in such misery? Maybe it’s a form of self-protection, but I find that when I experience a terrible comedy, I immediately block it from my memory, trying to pretend like it never happened. But occasionally, one of those duds will show up on cable or as a recommendation on a streaming platform. And then the nightmare comes back.

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Some cinematic turkeys have become infamous — they got terrible reviews, they lost a bazillion dollars — but to make my Top 10, they had to be really excruciating. Yes, I know people think Gigli blows, but it doesn’t reach the dregs of comedic desperation that you’ll find on this list. Also, I didn’t include stinkers such as Battlefield Earth or The Room, which are unintentionally hilarious because of how inept they are. To make my rankings, you had to be a comedy, and you had to be astoundingly awful as a comedy. 

I have to say: Writing about these films put me in such a depressed state. I haven’t thought about any of them for years, and I don’t want to think about any of them ever again. Who knew the emotional scars were still so fresh?

New Year’s Eve (2011)

God bless Garry Marshall, an icon whose career spanned writing for The Dick Van Dyke Show to creating Happy Days to directing Pretty Woman. (He was also hysterical in Albert Brooks’ Lost in America.) But later in life, he made a series of mediocre ensemble comedies built around specific holidays. Valentine’s Day and Mother’s Day were rough, but for my money, New Year’s Eve was the absolute nadir, crosscutting between a group of equally uninteresting characters on December 31st having varying degrees of clichéd misadventures. 

And now, I would like to present the list of actors in this abomination: Halle Berry, Jessica Biel, Jon Bon Jovi, Abigail Breslin, Robert De Niro, Josh Duhamel, Zac Efron, Héctor Elizondo, Katherine Heigl, Ashton KutcherSeth Meyers, Lea Michele, Sarah Jessica Parker, Michelle Pfeiffer, Til Schweiger, Hilary Swank, Taylor Swift and Sofía Vergara. Here’s the thing, though: One of the people I made up. Can you figure out who? I guarantee figuring out my riddle will only be slightly more entertaining than sitting through New Year’s Eve

The Master of Disguise (2002)

Dana Carvey was among the most popular Saturday Night Live performers of his age, but unlike fellow castmates such as Mike Myers, he was never able to parlay that success into solo movie stardom. The Master of Disguise would seem to have played to his strengths: This comedy-adventure, which Carvey co-wrote, is about a man named Pistachio Disguisey, a regular guy who learns that he has the power to transform himself into any persona he wishes. Soon, Carvey is doing all types of impressions, but unlike his George H.W. Bush or Church Lady, they’re all hacky and dumb. Though a modest hit at the time, The Master of Disguise has been largely forgotten — except, of course, for the legendary story of Carvey wearing a turtle costume while the cast and crew took a moment of silence for those who died during 9/11.

Space Jam: A New Legacy (2021)

LeBron James was very funny in Trainwreck playing an exaggerated version of himself who’s really into Downton Abbey. He should have stopped there — instead, he decided to do a sequel to Space Jam, the 1996 film that proved Michael Jordan should probably stick to basketball. 

In an era of nonstop I.P. recycling and rigid brand maintenance, Space Jam: A New Legacy was a soulless piece of product, with James teaming up with the Looney Tunes characters to do battle with the Goon Squad on the basketball court — all the while filling the screen with as many references to Warner Bros. movies and characters as possible. A year earlier, James had won the NBA championship with the Los Angeles Lakers — but with A New Legacy, all he gave us was an air ball.

The Hot Chick (2002)

Everybody’s got to start somewhere: Before Rachel McAdams was in Mean Girls or getting an Oscar nomination for Spotlight, she starred in a Rob Schneider vehicle. In The Hot Chick, she’s Jessica, a popular, snotty cheerleader who wakes up one day to find out she’s in the body of an adult man (Schneider). Unfortunately, this uninspired body-switch comedy is more about Schneider (playing a teen girl), which meant the far-less-talented actor of the two got center stage. 

“It was one of the hardest jobs I’ve had to date,” McAdams said, graciously, in 2016 about The Hot Chick, which helped launch her film career. She would go on to do much better comedies like Wedding Crashers and Game Night. As for Schneider, he would go on to become one more grumpy, aging comic whining about late-night being “indoctrination by comedic imposition.”

Zookeeper (2011)

There was a moment I thought Kevin James might have the goods to be a likable everyman movie star. That did not come to pass, and what clinched it for me was this woeful family comedy in which James plays a zookeeper who realizes, holy cow, all the animals can talk! What that leaves us with is a series of big-name actors and/or producer Adam Sandler’s buddies doing unfunny voice-overs as zoo creatures who try to help this affable loser woo a pretty veterinarian (Rosario Dawson). At least the awful Paul Blart: Mall Cop had a little manic energy to it — by comparison, Zookeeper was a listless, joyless affair. James’ film career was over soon after. 

Bucky Larson: Born to Be a Star (2011)

Of all of Adam Sandler’s pals who went on to star in their own movie, Nick Swardson laid the biggest egg. Sandler and Swardson were two of the writers on Bucky Larson: Born to Be a Star, which concerned the titular man-child who learns a shocking truth: His conservative parents used to be porn stars! Deciding to go into the family business, this naive Midwesterner sets his sights on Southern California, with hilarity not ensuing. 

A box-office bomb, Bucky Larson demonstrated that Swardson didn’t have the charisma or comedic chops to be a big-screen presence. And it helped earn director Tom Brady — not to be confused with Super Bowl champion quarterback Tom Brady — the unenviable distinction of helming two movies on this list. (The other is The Hot Chick.)

The Hottie & the Nottie (2008)

There was this really unfortunate period of time in American cinema when occasionally Paris Hilton would show up in a movie. The grating influencer’s worst flick is The Hottie & the Nottie, a tone-deaf romantic comedy in which she played Cristabel, the object of nerdy Nate’s (Joel David Moore) affections. They grew up together, and they reconnect in adulthood, but Cristabel explains that the only way she’ll date him is if he finds a guy for her best friend, June (Christine Lakin), who is, like, super-ugly! 

After spending most of its runtime mocking the unattractive, The Hottie & the Nottie has the nerve to argue that, really, what matters is being beautiful on the inside — but not before June undergoes a makeover and proves to be a hottie herself. Unfunny and insulting, the film deservedly sank without a trace.

Daddy Day Camp (2007)

If you want an indication of how bad this sequel to Daddy Day Care was, consider that neither of the original’s stars, Eddie Murphy and Jeff Garlin, bothered to come back for Part Two. Instead, Cuba Gooding Jr. and Paul Rae play the buddies, who decide this time to take over a struggling summer camp that they attended as kids. 

Lots of witless kids’ comedies appeal to obnoxious rugrats, throwing endless loud, stupid pratfalls at its young viewers. But Daddy Day Camp sunk to a new low, killing brain cells with its hyperactive inanity for 90 minutes. For the love of god, just have your children go outside and play rather than watch crap like this. 

The Emoji Movie (2017)

What if the Pixar braintrust had a stroke or decided to sell out big time? Then you might get this dreary Sony Pictures Animation disaster, which tried to build a whole movie out of the popularity of emojis. The plot follows an ordinary emoji (T.J. Miller) who goes on a quest to become “normal” — that is, only having one emotion — as he journeys through the circuitry of a smartphone, running into all kinds of apps along the way. 

The Emoji Movie was the single biggest ad disguised as a motion picture this century — look how cool Spotify and Instagram are, kids! — as well as being merely one of the many terrible movies that James Corden has been a part of. But maybe you’re not like me: If the idea of Patrick Stewart playing a poop emoji is your idea of hilarity, I have fantastic news for you.

Epic Movie (2007)

Which Jason Friedberg/Aaron Seltzer movie should top this list? Meet the Spartans and Disaster Movie are both deadly. What about Vampires Suck? Or The Starving Games? With all due respect to those utterly wretched pieces of garbage, the “winner” for me is Epic Movie, which is slightly more tasteless, insufferable and moronic than the writer-directors’ other efforts. 

A brain-dead parody of every hit movie the filmmakers can think of, Epic Movie cast everyone from Kal Penn to Jennifer Coolidge to Crispin Glover to a then-unknown Kevin Hart, sending up Pirates of the CaribbeanHarry Potter and Charlie and the Chocolate Factory. The film’s base, desperate gags were an insult to the memory of parody masterpieces like Airplane!, but audiences at the time couldn’t get enough of these utterly disposable spoofs. Eventually, the novelty wore off — Friedberg and Seltzer’s most recent film was 2015’s ignored Superfast! (a riff on the Fast and Furious franchise) — but Epic Movie will always stand as a testament to just how painful a bad comedy can be.

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