Julianne Hough's decision to darken her skin as part of a Halloween homage to OITNB character Crazy Eyes is just one in a long line of celebrity costume choices gone awry. The Daily Beast collected over a dozen examples of celebrity costumes that range from simply insensitive to blatantly insulting. Clockwise top left: Reuters, Instagram, X17, Fame Hilary Duff and and her new boyfriend, trainer Jason Walsh, apparently did not consider the consequences of turning up at the Casamigos Halloween Party on Friday night as a sexy pilgrim and a face-painted Native American “chief.” The internet, predictably, went nuts, and Duff was forced to apologize Sunday. “I am SO sorry to people I offended with my costume,” she tweeted. “It was not properly thought through and I am truly, from the bottom of my [heart] sorry.” Michael Kovac/Getty Images Pretty Little Liars star Ashley Benson knew she messed up, but the internet never forgets. Last year, the actress was trying on potential Halloween costumes and posting photos to her popular Instagram account, and in one, she posed in a sexy lioness costume replete with the caption, "What do you guys thing of this Cecil the Lion costume?" Needless to say, her followers were none too impressed with her choice of the famously murdered African lion, and Benson quickly deleted the post and re-captioned it. Sadly enough, the outfit she was trying on is an actual thing. The website Yandy.com is offering a skimpy "Cecil the Lion" costume for the grand total of $118.95. via Instagram This costume should have probably ended with the prison uniforms. But actress Julianne Hough took it a step further, covering her face in dark makeup to portray the character nicknamed "Crazy Eyes" (played by Uzo Aduba) from Netflix hit Orange is the New Black at the Casamigos tequila Halloween party in Hollywood back in 2013. Pro tip: blackface is never a good idea. Devone Byrd/Pacific Coast News,Devone Byrd, PacificCoastNews In October 2014, the pop star Kesha sued her longtime producer Dr. Luke (aka Lukasz Gottwald), alleging a pattern of sexual assault, battery, sexual harassment, and emotional abuse over the course of their 10-year professional relationship. So that Halloween, singer Lily Allen decided to dress up as Kesha's alleged tormentor for Halloween. Too soon. Way, way too soon. Twitter Possibly the pinnacle of Prince Harry's controversial array of missteps was when he donned a swastika armband and other Nazi garb at a party in 2005. Sure, it wasn't a Halloween party, but Jesus, man! Two weeks later his grandmother led the country's Holocaust memorial events. Reuters,© Reuters Photographer / Reuters In 2010, socialite Paris Hilton attended the Playboy Halloween Party dressed in a sexy Native American costume, replete with darkened skin and headdress. To call this racially insensitive would be a massive understatement. Then again, Hilton has been known to dabble in racist behavior. X17 Famous for her elaborate costumes and blowout Halloween bash, supermodel Heidi Klum arrived to her 9th annual Halloween party at 1 OAK in New York dressed as Hindu goddess Kali, replete with a severed head hanging from one of her many arms. Hindu leaders were upset by her depiction of the sacred figure, calling her out for being disrespectful and using Hindu culture as a publicity stunt. Joe Corrigan/Getty,Joe Corrigan Because Chris Brown is physically incapable of doing anything uncontroversial, in 2012 he arrived at Greystone Manor in West Hollywood in a full Taliban soldier getup. Not sure how the commanders would feel about studs in the vest, Chris. X17,Maciel-WL/X17online.com Apparently, Nicky Hilton didn't learn a damn thing from her sister's 2010 costume catastrophe. Last year, she attended the Casamigos Halloween Party dressed in, yup, a sexy Native American getup. Rich kids. Getty Colton Haynes is the star of the MTV supernatural tween show Teen Wolf, as well as the vigilante Roy Harper/Arsenal in CW's superhero series Arrow. He is also one of the more problematic celebrity Halloween guests you're likely to come across. In 2011, Haynes took it upon himself to don blackface as hip-hop icon Kanye West, and the following year, he browned his skin to portray Gandhi. SMH. Twitter Last year, country star Jason Aldean took it upon himself to sport blackface and dreadlocks as part of a Lil Wayne Halloween costume. Jason: Stick to your shitty country music. Nationalgab.com Maybe "Disco Africa" wasn't the best party theme to begin with. The party, held last weekend in Milan, was attended by Italian designer Stefano Gabbana, in feathers and leopard print, who posed with a guest covered in tribal stripes and the blackfaced designer Alessandro Dell'Acqua. Instagram Not long after the horrifying allegations of ongoing child sex abuse at Penn State, Jeff Ross, dressed as the late football coach Joe Paterno, arrived for the Comedy Central Roast of Roseanne Barr in Los Angeles in 2012 flanked by two shirtless football players. “If they’re offended by what they see, they can do what Joe Paterno did—look the other way,” he told reporters. Phil McCarten/Reuters,é Phil McCarten / Reuters Sitting next to his then-girlfriend, a bemused Whoopi Goldberg, actor Ted Danson painted his face black and spewed a n-word routine for the New York Friars Club Roast in October 1993. Goldberg later admitted she had written the offensive jokes which had stirred up such a controversy. Richard Corkery/NY Daily News Archive, via Getty