15 Movies Where Comedians Lost Their Funny

Credit: Ryan Zeinert

15. Jim Carrey – Me, Myself & Irene

For the argument, we’re going to let The Cable Guy slide on this one. From that point forward in his career, Carrey hasn’t been able to be taken seriously as a talented actor, nor has he been able to transition back into the comedies that made him a superstar. His status is not to be envied; he’s a man without a country. For my money, he should have wrapped it up the second that the credits started rolling in Man On The Moon.


14. Denis Leary – Operation Dumbo Drop

When this was released, I couldn’t even believe it was a real movie. It sounded to me like a film that Homer Simpson would have dreamed up, like Editor in Chimp, or Giraffe in Charge. For all the things that Denis Leary has done correctly in his career (we’ll let his thievery of Bill Hicks’ shtick slide), this was the film where we realized that he’d do just about anything for cash.

13. Dana Carvey – The Master of Disguise

I might be in the minority, but I like Dana Carvey. His 1995 HBO Comedy Special will be quoted by millions until the end of time, and his work with SNL-based projects was nothing short of legendary. But The Master Of Disguise… Jesus. I have to be completely honest with you; I haven’t even seen this movie. But seriously now, have you? The previews for this film were about as annoying as that Six Flags commercial where the borderline-terminal geriatric dances about the theme park. Almost poetically, this was the last film that Dana Carvey has made.

12. Jim Breuer – Half Baked

I’ll make this one quick. Half Baked reminded us of what we already knew about Jim Breuer. Need I continue?

11. Janeane Garofalo – The Truth About Cats and Dogs

For the span of a few years, Janeane Garofalo was the Generation X comic. She talked about things relevant to the decade, she starred in Reality Bites, one of the quintessential Generation X films, and was even sort of attractive in a Generation X sort of way. Then, at some particular point in the last 90’s, she just decided that telling jokes was just too much work. Instead, she dove horn-rimmed glasses-first into the fulfilling career of bitching and complaining about absolutely everything. Liberal comedians always feel that they can make the jump from jokes to politics effortlessly, but all it usually does is make decent liberals look like jackasses.
10. Carrot Top – Chairman of the Board

Okay, this one might be a little too easy and perhaps a little malicious, as Mr. Top really only starred in one feature film. But really, did you think I’d miss the chance to pick on one of the most hated and disrespected comedians of all-time? Hell, the only reason that Carrot Top started hitting the weight rooms and steroid clearinghouses was to protect himself from the hecklers. While Chairman of the Board did little to nothing to help cement Carrot Top’s status as hack extraordinaire, it sure as hell didn’t help him any. Poor guy; at least he has his props to keep him company at night. And his millions of dollars. And probably a hooker or two.

Bonus vid: Norm MacDonald discusses Chairman of the Board with Conan O'Brien.

9. Will Ferrell – Semi-Pro (His Fourth Sports-Themed Film)

Will Ferrell is a funny guy. He makes an assload of cash, millions adore him, and pretty much every film with his name on it goes straight to #1. Talladega Nights was decent enough, Kicking and Screaming was a good family film, and Blades of Glory was… Jesus, did he just do three sports movies in a row? By the time that Semi-Pro was being promoted, audiences finally caught on to the fact that Ferrell more or less accidentally turned himself into a one-trick pony, as Steve Carrell started gobbling up roles that Ferrell used to be the shoo-in pick for. Whoops.

8. Jerry Seinfeld – Bee Movie

When Seinfeld said its final goodbye in 1998, America was clamoring for Jerry Seinfeld to do something, anything that would keep him in the public eye. Apart from some stand-up dates and late-night appearances, Jerry more or less disappeared, taking his money and Porsche collection and locking the doors. As one of the greatest television stars of the last 25 years, it seemed almost impossible for the public to tire of Seinfeld and his neurotic, slice-of-life comedy. This all changed in 2007, when Seinfeld emerged to heavily (and I mean heavily) promote his film, Bee Movie. It was then that we saw a new side of Seinfeld (and by ‘new,’ I mean ‘recently ignored’); arrogant, shill-tastic, overbearing and kind of an ass. Bee Movie was over hyped into oblivion, and America experienced something that we thought we never would; we were completely and entirely sick of Jerry Seinfeld.

7. Chris Rock – Everything (Although New Jack City was awesome)

There is no question that Chris Rock continues to be one of the funniest men on the planet, if not the greatest stand-up comic currently working today. That all being said, his transitions to the silver screen are almost always atrocious. Besides a role in Dogma and his classic, early crackhead role in New Jack City (still his best portrayal yet), Rock has yet to find a way to transpose his stage brilliance to the screen. Even if this never happens, I think we can all let it slide.
6. Adam Sandler – Little Nicky

Now, I know that there’s a lot of people out there that will argue that Adam Sandler has never been anything but a hilarious leading man that takes risks and always maintains his status as one of comedy’s only sure things. These people have obviously never seen Little Nicky. Don’t get me wrong, Adam Sandler is still relatively funny and seems to be a huge box office draw, but this was his own personal Vampire In Brooklyn; one of the few times where he was chastised across the board, and nearly didn’t recover. Sure, he’ll never replicate the Billy Madison/Happy Gilmore success he had in the past, but as long as he shies away from Little Nicky-esque films in the future, at least he’ll still be able to get work.

5. David Spade – Everything After Chris Farley Died

Poor, poor David Spade. After back-to-back successes that included Tommy Boy and Black Sheep, he lost his best friend and acting superior, Chris Farley. From that point forward, Mr. Hollywood Minute just hasn’t been the same, making it very clear that if he’s not playing the ‘little buddy’ of an overweight comedic genius, he’s more or less destined to the dollar bin at Blockbuster Video.

4. Dane Cook – Employee of the Month

It could be easily (and reasonably) argued that Dane Cook ceased being funny the very second that his heartbeat showed up on his mother’s ultrasound, but for the sake of this list, we’ll give the distinction to Employee of the Month. While Cook still had a relatively large and naïve fan base when Waiting was released, Employee of the Month was the film that reduced Cook’s core audience to nothing more than backwards baseball cap-wearing fratboys who incessantly quote his unfunny rubbish and non-existent punchlines.
3. Jack Black – School of Rock

First off, I understand that School of Rock is a halfway-decent movie that earned Jack Black a spot on the Hollywood A-List and guaranteed his admission to every Nickelodeon Kid’s Choice Awards until the end of time. However, it was School Of Rock that changed Jack Black from an adult-themed, overweight slacker icon to a fun-loving, Kung-Fu Panda-starring celebrity for children. I’m sure his paychecks are much bigger than back in the Tenacious D days, but at what cost?

2. Robin Williams – Patch Adams

One of my favorite criticisms of Robin Williams is, “He does cover versions of other comic’s jokes.” By that regard, Robin Williams has been known for years as the best Talented Comedian Tribute Act on Earth. While I personally never thought that his coked-up, manic, ADD-riddled bullshit was ever humorous in the least, we can look to Patch Adams as the precise moment that Robin Williams ceased to be relevant in the eyes of everyone except soccer moms and parents of the terminally ill. After Sam Kinison, Bill Hicks, Mitch Hedberg and Lenny Bruce all left us way too soon, why must we still have to tolerate what could be the least creative comic that ever lived?

1. Eddie Murphy – Vampire in Brooklyn

My question is this. Who has been funding the last ten Eddie Murphy movies? For those of us that grew up in the 70’s and 80’s, Eddie Murphy was the funniest guy on the planet. A guy that influenced such current greats as Chris Rock and Dave Chappelle, his Saturday Night Live, Raw, 48 Hours and Beverly Hills Cop moments outshine some of the greatest comics that ever straddled the live between the stage and big screen. For a new generation of kids, however, Eddie Murphy will always be remembered as the megalomaniac over-actor that insists on strapping into a fatsuit for every picture. Eddie, for the good of your legacy, please hang it up. Get your jacket from Raw bronzed and disappear from the limelight forever.