15 of the Most Embarrassing Movie Roles of All Time

The quest to become an actor in Hollywood is humiliating as it is. You would think that getting some work in a major motion picture means you’re done with the embarrassing pandering. As evidenced by some of the roles they create, Hollywood screenwriters disagree. Here are 15 movie roles so embarrassing, it almost makes you happy that you’re a cog in a soul-crushing office cubicle.

Benicio Del Toro as the Dog Faced Boy

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Generally, actors are hired because they are handsome. Unfortunately, they sometimes get a role that requires them to look like they fell out of the ugly tree and hit all the branches on the way down. Maybe it’s because of his naturally hairy face that Del Toro was tapped to play Duke the Dog-Faced Boy in Big Top Pee-Wee.

Cuba Gooding Jr. as Fake Gay Guy

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As if trying to sell Cuba and Horatio Sanz as “ladies men” wasn’t a tough enough sell, Boat Trip is probably one of the most painful comedies you wished you never sat through. Released in 2002, long after gay stereotype jokes ceased to be funny, Cuba took a page from the Harrison Ford book of comedy.

Nicolas Cage as Randy the Punk

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The term “Valley Girl” might’ve been hip and trendy back in 1983 when they made the movie Valley Girl. Nicolas Cage doesn’t mind getting his hands dirty playing a crazy vampire guy, drunk, or criminal with his face torn off. But in this one, he’s the handsome young punk that wins the girl with dialogue so horrible, you may throw yourself in a valley rather than hear anymore. You know a movie is in trouble when the film makers tout the music in it.

Matthew McConaughey as Vilmer Slaughter

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You’d think with a name like “Vilmer Slaughter” McConaughey would be playing a wrestler or some king of daredevil stuntman. Unfortunately, this role was part of Texas Chainsaw Massacre: The Next Generation. It’s kind of like Star Trek: The Next Generation, only instead of a bald spaceman exploring the galaxy, a guy with a leather face explores people’s internal organs with a chainsaw. As a bonus, McConaughey plays a murderous trucker with a cybernetic leg. Shakespeare it is not. (Yes, that is Renee Zellweger as one of the screaming teenagers.)

Vanilla Ice as Johnny

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It’s embarrassing enough to be Vanilla Ice, just imagine the additional humiliation of being in a movie called “Cool as Ice”. Who would’ve thought that there would be a movie that made Teenage Mutant Ninja Turtles II: The Secret of the Ooze look like an Oscar contender? Rumor has it that James Dean actually came back from the dead, but then immediately went out and drove into a tree after seeing this movie.

Arnold Schwarzenegger as Hercules

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When you’re an athlete-turned-actor, you tend to get typecast. Before Arnold finally found his groove with Terminator, Predator, and other roles that made him look like an emotionless killing machine, he was cast in “Hercules in New York.” To add insult to injury, the thick-accented Austrian was billed as “Arnold Strong”.

Jim Carrey as Bobby Todd

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What could be more embarrassing than playing a horndog in an 80’s ski comedy? Getting paired with Alan Thicke in the movie, “Copper Mountain”. Double bonus points for doing an awful imitation of Steve Martin. Thank God he was able to recover his dignity in Ace Ventura.

Frank Langella as Skeletor

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So, you’ve built up an impressive acting resume doing theater and playing roles like Dracula and Sherlock Holmes. Now the studio wants you to play an action figure without a face. Frank Langella must’ve felt like he was slumming in the 1987 movie Masters of the Universe. Playing second banana to a thespian like Dolph Lungren was probably not painful at all. As a bonus, it’s one of Courtney Cox’s earliest movies.

Ben Kingsley as Guru Tugginmypudha

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The name of this character alone should’ve sent Kingsley back to his agent with a baseball bat to beat some sense in him. How embarrassing is it not only to play a part in a painful comedy like the Love Guru, but to become a parody of yourself after playing Mohandas Ghandi in an Oscar-winning movie? It would be like Dustin Hoffman appearing in an 80’s teen sex comedy sometime after his role in The Graduate or Mike Meyers ruining the Graduate. Leave the real actors alone Mike.

Everyone Involved in Ishtar

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Ishtar is a movie of such legendary badness, one wonders how the actors ever auditioned again with a straight face. Dustin Hoffman and Warren Beatty star as two lounge singers lost in the desert, who somehow get involved with spy stuff. Max Headroom, Charles Grodin, and Carol Kane also appear. Rumor has it, the first projectionist to run this movie hanged himself with a sign on his chest that said, “Cinema is dead.”

Jeff Goldblum as Freak #1

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You know it’s a depressingly bad role when your character doesn’t even get a name. Goldblum played one of Charles Bronson’s targets in the famous Death Wish movie. He sort of looks like a mean, weird version of Jughead in this scene.

David Hasselhoff as Boner

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Usually with a name like “Boner” you’re talking about a character that appeared in a fake movie on The Simpsons. But this time, we’re talking about David Hasselhoff in “Revenge of the Cheerleaders”. This is probably more embarrassing than his cheeseburger video.

Jennifer Aniston as Leprechaun Bait

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Leprechaun was made in 1993 and starred Jennifer Aniston. It’s unlikely after making gagillions of dollars on Friends, she would’ve agreed to this horror movie full of Irish stereotypes and questionable puppetry. Aren’t leprechauns supposed to be friendly and bring you sugary cereal anyway?

Sylvester Stallone as Stud

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Sylvester Stallone’s brief stint as a pornstar in “The Party at Kitty and Stud’s” is legendary. Embarrassing as the role might be, it’s still probably a better movie that Stop or My Mom Will Shoot and Rhinestone combined.

Divine as Babs Johnson

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The most embarrassing and humiliating movie role of all time, hands down, goes to drag queen Divine, in Pink Flamingos. John Waters, in his early days, really stretched the bounds of film making with one of the most disgusting on-screen “food scenes” of all time. In it, Divine eats dog poo, fresh from the dog’s ass. Click if you dare.

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