Halloween is a time for children and adults alike — a time for dressing up as your favorite character to trick-or-treat or hit up a few parties.
It is time to celebrate and have fun, but for some people, it is a time to see just how far they can push the line.
Hollywood celebrities are no exception to this rule, and from donning blackface to making fun of drug overdoses, some of them just can’t figure out when a costume goes from being funny or weird to just plain offensive.
Let’s start thing out with one of our favorite comedians: Bill Murray. In 2010, this celebrity decided to be Jimi Hendrix.
He wore blackface and dressed in a flouncy, purple scarf and flowing, yellow shirt accessorized with an electric guitar.
TB to 2010 when Snooki offended parents across the country with her missing girl milk carton Halloween costume pic.twitter.com/lanpYd87bj— Anna Florczak (@Anna_Florczak) October 19, 2015
In 2010, Snooki celebrated Halloween by making light of missing children. She wore a milk carton on her head with a cutout for her face, making her the girl on the milk carton.
The costume likely dredged up painful memories for every parent who has ever lost a child.
In 2009, model and reality television personality Adrianne Curry dressed as Amy Winehouse.
Her outfit came complete with a fake heroin-filled syringe and camouflage T-shirt. Curry’s Halloween costume came just two years before Winehouse’s fateful drug overdose.
Instead of blackface, Heidi Klum chose blueface in 2008.
Klum is known for going over the top with her Halloween costumes, but with this one she really outdid herself. Her costume offended countless Hindus, especially when she explained she chose to be the goddess because “she’s so mean and killed all these different people and [had] fingers hanging off [her] and little shrunken heads everywhere.”
In 2010, Paris Hilton found herself at a Halloween party at the Playboy mansion. Her costume of choice? A Native American woman.
Dressing up as a Native American for Halloween is a debate that is held nearly every year, and each time the consensus is the same: It is not okay. But that didn’t stop Hilton wearing a feathered headdress and animal-skin bikini.
Five years after her sister’s controversial costume, Nicky Hilton decided to followed exactly in her footsteps.
In 2015, Hilton also dressed as a Native American woman. She braided her hair and wore a beaded headband and top in just another example of cultural appropriation.
Nadya “Octomom” Suleman became famous after having octuplets, but in 2009 her fame was renewed after dressing as a pregnant nun with devil children.
The mother of eight had a silver cross draped around her nun costume and dressed each of her kids as devils, complete with a red jumpsuit and little, black horns.
Miami Heat star Dwyane Wade flipped blackface on its head when he dressed up as Justin Timberlake for Halloween in 2010.
With a hat resting atop a blonde wig, Wade wore a white shirt with a black vest and tie, and used white face paint to lighten his skin, and blonde paint to lighten his eyebrows and goatee.
Colton Haynes: wanted to be Kanye and then Ghandi pic.twitter.com/2KChbBG2DO— QUEENSONLY (@nk1isontheway) July 17, 2017
In 2011, Teen Wolf and Arrow star Colton Haynes thought it would be clever to wear blackface and dress as Kanye West for Halloween.
He wore a long, gold chain around his neck and a black sweatsuit, with gold-rimmed sunglasses to pull the costume together. The following year, he wore blackface again, this time dressing as Mahatma Gandhi.
This tickled me. Chris Brown takes time out from beating up Rihanna to dress up as a terrorist. pic.twitter.com/C1iLw9Jm— Tom Callaghan (@tomcallaghan3) November 3, 2012
There’s a lot of offensive Halloween costumes out there, but Chris Brown dressing as renown terrorist Osama bin Laden in 2012, and his vulgar reaction to the ensuing public outcry definitely takes the cake.
Brown wore a turban and slung a bandolier filled with ammunition over his shoulder. Before setting out for the night, he tweeted a picture of himself with the caption, “Ain’t nobody f—ing wit my clique!!!”
Naturally, America was rather upset with Brown for his insensitive costume choice, and loudly voiced their concerns. But instead of apologizing, Brown ratcheted it up by telling people “who really mad about it: F— y’all.”
Which do you think is the most offensive Halloween costume?