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Shaun White As ‘Simple Jack’
U.S. Olympic snowboarder Shaun White looked all the way back to 2008 for his ill-conceived Halloween costume. Dressing as “Simple Jack”, a character from the Ben Stiller comedy “Tropic Thunder”. In the film, Stiller’s character, an actor, plays Simple Jack, a mentally challenged man - very poorly - in an attempt to land an Oscar and is meant to be a send-up as the shameless lengths some stars will go to win awards praise. But 10 years later that was lost on White who quickly came under fire for his costume, earning particular ire from the Special Olympics for his outfit.
White apologized after the backlash: “I owe everyone in the Special Olympics community an apology for my poor choice of Halloween costume the other night. It was a last-minute decision. It was the wrong one. The Special Olympics were right to call me out on it. They do great work supporting so many tremendous athletes and I am sorry for being insensitive. Lesson learned.”
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Harry Hamlin And Lisa Rinna As Sid And Nancy
Inspired by a 1978 photo of Sid Vicious and girlfriend Nancy Spungen, Harry Hamlin and Lisa Rinna caused controversy with their Halloween costumes at a 2015 Casamigos tequila party.
Aside from the fact that Sid would go on to murder Nancy, Hamlin also opted for a shirt with a swastika emblazoned on it. The couple apologized the next day on Instagram: “If I hurt you, we were being authentic to the characters of Sid and Nancy for our Halloween costumes. It hurt and angered many of you and we are deeply sorry for that. That was never our intention. We did not mean to offend. With love, Lisa and Harry.”
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Ted Danson’s Shocking Performance
While he was not technically wearing a Halloween costume, Ted Danson dropped jaws with his performance at the October 1993 Friars Club Roast. Known for shocking humour and raucous behaviour, Danson showed up at the private event in blackface, dropping the N-word more than a dozen times and ate a watermelon on stage during his racist performance. Celeb guests, including Vanessa Williams, Halle Berry, Mr. T and RuPaul, reportedly sat stone-faced while Montel Williams turned his back to the stage in protest.
Danson’s then-girlfriend Whoopi Goldberg later admitted to writing the offensive routine for Danson to recite at the roast.
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Luann de Lesseps As Diana Ross
Luann de Lesseps made headlines on “Real Housewives Of New York City” for her "Diana Ross" Halloween costume. While viewers lashed out because of her skin, which appeared darkened for the costume, she denied donning blackface in a tweet: "I in no way altered my skin color and I did not mean to offend anyone."
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Kylie Jenner As An ‘Eskimo’
In 2015, Kylie Jenner stepped out for Halloween in a fur-lined, midriff-baring ensemble she dubbed “Eskimo” on Instagram. After users called her out for using the slur term for her look that’s meant to be inspired by what she takes to be traditional Inuit dress, she updated the caption on one of her posts to read “Snow Princess”. We’re still not buying it, Kylie.
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Colton Haynes In Blackface – Twice!
It seems former “Teen Wolf” actor didn’t learn his lesson in 2011 after putting on blackface to become Kanye West at a Halloween party. The following year, he once again donned blackface, this time around masquerading as Gandhi on Halloween. In 2013, Haynes finally clued in that blackface was offensive and demeaning. He posted an apology video saying he wasn’t aware he was “offending people” but rest assured, that “wasn’t [his] intention at all.”
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Bill Maher As Steve Irwin
Talk about poor taste! In 2006, less than two months after the death of Steve Irwin, Bill Maher dressed up as “Crocodile Hunter” the barb of the stingray that killed him sticking out of his bloodied chest for Halloween. After drawing criticism for his costume, Maher refused to say he was sorry. "You want me to apologize for making a joke?” he quipped on his show “Real Time With Bill Maher”. “People who really love animals understand if you get killed by one, chances are you were doing something to it you shouldn't have been.”
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Scott Disick As An Arab Sheikh
Lord Disick caused quite the controversy when he dressed as an Arab Sheikh for Halloween in 2014. Sharing his costume with his millions of Instagram followers, Disick wished them, "Happy Halloween! We getting Arab money tonight,” as he posed next to two luxury vehicles.
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Kelly Osbourne As Rachel Dolezal
In the weeks following Rachel Dolezal's resignation from her post at the NAACP, Kelly Osbourne chose to mock the controversial figure. The costume was considered out of line for many of Osbourne’s fans.
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Jason Aldean As Lil Wayne
That same year, country singer Jason Aldean showed little remorse after offending fans and the Twittersphere with his Lil Wayne costume. Shortly after being photographed in the blackface costume, the star didn't seem sorry for the controversial getup. “In this day and age people are so sensitive that no matter what you do, somebody is going to make a big deal out of it,” he said. “Me doing that had zero malicious intent … I get that race is a touchy subject, but not everybody is that way. Media tends to make a big deal out of things. If that was disrespectful to anyone, I by all means apologize. That was never my intention. It never crossed my mind.”
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Heidi And Spencer Pratt As Jon And Kate Gosselin
Heidi and Spencer Pratt mocked “John & Kate Plus 8” stars Jon and Kate Gosselin as the couple of eight children were in the midst of a nasty divorce.
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Lily Allen As Dr. Luke
Lily Allen should have thought twice when she made light of controversial producer Dr. Luke and his sexual assault battle with Kesha. Many questioned her taste when she attended Kate Hudson's Halloween party in doctor scrubs and a name tag that read: "Dr. Luke, gynaecology department."
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Prince Harry As A Nazi
No surprise here! Prince Harry made front page news when he dressed as a Nazi while attending a Halloween party in 2005.
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Heidi Klum As A Hindu Goddess
Halloween fanatic Heidi Klum spares no expense when it comes to her yearly costume, but in 2008 the supermodel went a little too far according to some angry onlookers. The former Victoria’s Secret model offended many Hindus when she arrived at her Halloween extravaganza dressed as Hindu goddess Kali.
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Hilary Duff And Jason Walsh As Pilgrim And Native American
Hilary Duff and ex-boyfriend Jason Walsh raised eyebrows in 2016 when the pair committed the Halloween faux-pas of dressing as a pilgrim and a Native American. Duff would later go on to apologize for the controversial costume, tweeting: ”I am SO sorry to people I offended with my costume. It was not properly thought through and I am truly, from the bottom of my [heart emoji] sorry."
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Chrissy Teigen And John Legend As Indian And Cowboy
Following in Duff and Walsh’s missteps are Chrissy Teigen and John Legend, who chose Cowboys and Indians as their 2008 couple’s costume of choice.
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Ashley Benson As Cecil The Lion
In the months following the killing of Cecil the Lion, Ashley Benson made the questionable decision of dressing as the murdered animal for Halloween. "Help! Can't decide on my Halloween costume this year! What do you guys thing of this Cecil the Lion costume?" Needless to say, the decision did not go over well with many of her “Pretty Little Liars” fans.
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Chris Brown As A Terrorist
Few were surprised by the controversy that followed after Chris Brown attended Rihanna’s Halloween party dressed as a Taliban terrorist.
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Nicky Hilton As A Native American
In 2015, after years of similar errors in judgement by her fellow celebrities (and sister Paris), Nicky Hilton made the major mistake of dressing as a Native American while attending Casamigos’ annual Halloween party.
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Julianne Hough As Crazy Eyes
“Dancing with the Stars” mainstay Julianne Hough set off a wave of Twitter backlash when she donned bronze blackface while attending a Halloween party as Crazy Eyes from “Orange is the New Black”.
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