Heidi Klum – Goddess Kali
Super-model Heidi Klum has become sort of a Hollywood legend for her extensive and ornate Halloween costumes over the years. As a matter of fact, most of the time you can’t even tell who is behind the makeup or masks.
However, Heidi’s idea to dress up as the Goddess Kali fell flat as Hindus around the world took offense in 2008. Hmmm... Maybe it was the severed heads, or the knife-wielding that did it...
Hillary Duff and Jason Walsh - Native Americans
In 2016, actress Hilary Duff and then boyfriend, Jason Walsh, donned sexy matching Pilgrim and Indian costumes. Pretty insensitive at the time, considering that the North Dakota pipeline protests were growing more and more volatile.
They won the prize for being the first celebrities to apologize for a Halloween costume faux pas in 2016 considering they released their apologies on their separate Insta accounts on All Hallows Eve.
O.J. Simpson – Gynecologist
Okay, so maybe this one isn’t so much controversial as just in bad taste. O.J. Simpson, formal football super-star-turned-con, is most commonly known now for having killed his wife and her lover and for the most part got away with it.
The ex-con dressed as a gynecologist named Dr. Seymour Bush. But instead of being offended by the costume, bar guests lined up for selfies and autographs.
Chris Brown – Terrorist
As if he didn’t have enough controversy in the media already at the time, in 2012, Chris Brown made headlines once again. This time it was for his choice of Halloween costume.
Brown and a bunch of his friends thought it would be cute to dress up as Muslim terrorists for Halloween in 2012. The internet did not agree.
Scott Disick – Sheik
In 2014, then honorary Kardashian, Scott Disick thought it would be fun to play Arab Sheik for Halloween. He posted a pic of himself in costume with the caption “We getting Arab money tonight.”
While many didn’t see any harm in the costume, there were many who were disappointed with the reality star’s choice of cultural appropriation. Disick never apologized for the costume, but eventually Khloe Kardashian did once she realized their faux pas.
Ashley Benson – Cecil the Lion
Flashback to Halloween 2015 and the uproar (pun definitely intended) was over Ashley Benson’s idea of a funny costume. When the actress posted a photo of her wearing a sexy lion costume, her original caption made a reference to the lion that had recently made headlines for being slain on protected grounds.
After several users let her know that they thought her costume idea was offensive, the Pretty Little Liars star changed the caption to just say lion. She later defended herself by saying she only wore the costume for a few minutes and took it back off.
Kim Kardashian – Aaliyah
I mean. Could we really make a list about controversial celebrities and not include at least one of the Kardashians? Kim faced backlash back in 2017 for her Aaliyah costume.
Although, the costume itself surely set the internet ablaze with commentary, it was her apology statement that really set the world off when she claimed that “We don’t see color in my home.” People of color were even more offended at that statement since her husband and child(ren) are black.
Julianne Hough – Suzanne “Crazy Eyes” Warren
In 2013, Orange Is the New Black hit Netflix and the world had a new obsession. Apparently, Julianne Hough was also obsessed and decided to portray one of her favorite characters of the show for Halloween that year—complete with blackface makeup.
Another celeb who arrived at the party at the same time tried to get to Hough quickly to tell her to take off the blackface makeup before photos were taken, but alas, she was too late. The photos of the celeb in blackface quickly made the rounds on social media and Hough was forced to post a formal apology the next day.
Ashley Tisdale – Sugar Skull
This one is still debatable. In 2016, when High School Musical alum, Ashley Tisdale, attended gal pal Vanessa Hudgens's Halloween bash dressed up as a sugar skull, the Internet was set on fire immediately.
Many were angry at the actress for cultural appropriation. Still, many defended the actress, stating that it was considered a costume in Mexican culture as well.
Shaun White – Simple Jack
In 2018, Olympic gold medalist, Shaun White, attended a Halloween party dressed as Simple Jack from the 2008 film Tropic Thunder. Almost immediately the Special Olympics blasted the Olympian for setting a bad example. They made a statement to Huffpost.com, “…Disability is not a joke, nor should it be a punchline…”
The three time Olympic champion apologized almost immediately. His response was, "I owe everyone in the Special Olympics community an apology for my poor choice of Halloween costume the other night," White said in a statement on social media. "It was a last minute decision. It was the wrong one. The Special Olympics are right to call me out on it."
Prince Harry – Nazi
In January of 2005, Prince Harry thought it would be funny to dress up as a Nazi to a friend’s fancy costume party. Unfortunately, a photo of him in the uniform leaked to the press and ended up all over The Sun tabloid cover in time for the afternoon edition.
In January of 2005, Prince Harry thought it would be funny to dress up as a Nazi to a friend’s fancy costume party. Unfortunately, a photo of him in the uniform leaked to the press and ended up all over The Sun tabloid cover in time for the afternoon edition. Funny enough, this is the only copy of the photo that still exists, today.
Jeff Ross – Joe Paterno and Company
Okay so this wasn’t for Halloween, but it’s pretty controversial. Jeff Ross showed up to Roseanne Barr’s comedy roast dressed as Jerry Sandusky—or more commonly known to Penn State fans as JoePa—with two boys dressed in nothing but towels and football helmets.
The comedian, who admitted his costume was controversial, claimed that he was making a statement. We think the statement may have been lost, here.
Chrissy Teigen – Native American
In 2008, Chrissy Teigen and John Legend attended a Halloween party, Legend as a cowboy and Teigen in full Native American regalia. This immediately sparked outrage across the interwebs.
Although it sparked controversy, Teigen stated that, “It was, to me, very cute, but now thinking back I’d never do it again. Bad idea, Chrissy, bad idea!”
Jemima Khan – Melania Trump
Okay. But this one is funny. In 2016, British journalist Jemima Khan attended the UNICEF Halloween Ball in London dressed as Melania Trump with a dummy of an apparent Donald Trump wrapped around her back, reaching for—well—you can see what he’s reaching for, there.
She was also holding a sign that said “Trump 2016… Vote on 28th November!!!” This was poking fun at Trump since the date of voting in 2016 was November 8th and Trump told his supporters several times to vote on November 28th. And as if she hadn’t already made a statement, Khan was holding papers that read, “Michelle Obama’s Convention Speech.”
Tia Mowry – Geisha
In 2013, Tia Mowry decided to dress as a traditional Japanese Geisha for her Halloween party. Many of her Insta followers were not impressed. One user commented “My race and the races of others are not a costume for a cheesy holiday.”
Another commented, “Please do some research on cultural appropriation. Geisha costumes are not cool, girl.” However, the actress wasn’t daunted because she never removed the post nor apologized for it publicly.
The Chainsmokers – “Ebrola”
Okay, so this one wasn’t Halloween either, but it’s pretty offensive. During the 2014 Ebola pandemic the EDM-pop duo, The Chainsmokers, dressed up as “Ebrola” health care workers while playing at a frat house.
The epidemic at that point had so far claimed more than 5,000 lives and was nothing to sneer at. However, these guys found a way to turn it into a joke and never apologized.
Bill Maher – Dead Steve Irwin
Just barely more than a month after Crocodile Hunter, Steve Irwin, was killed by a stingray while filming on the Great Barrier Reef, Bill Maher decided to shock the world by dressing up as Irwin.
While dressing up as the zoologist might not have made headlines, the fact that it was a bloody costume with a stingray tail sticking straight out of his chest. And what made it worse? The comedian refused to apologize for the costume because he figured Irwin may have “been doing something” to the stingray that he shouldn’t have been.
Harry Hamlin – Sid Vicious
Apparently, celebs never learn from those that have come before them. In 2015, Harry Hamlin and girlfriend Lisa Rinna dressed up as infamous Sex Pistols bassist Sid Vicious and his just as infamous girlfriend Nancy Spungen for a party on a Friday night.
That would have been all well and good, and no one might have batted an eyelash, had Harry not chosen a red t-shirt with the image of a swastika on it to portray Sid. By Monday morning the pair were both on Instagram trying to accomplish damage control.
Kylie Jenner – Eskimo
I mean. Are we surprised that yet another Kardashian has appeared on this list? On Halloween of 2015 Kylie Jenner posted a photo of herself dressed up on Insta with the caption “Eskimo.”
She later changed it to say “Snow Princess” after she came under fire for her offensive remark, but many were not buying it. The term Eskimo is generally considered a slur, and fans did not appreciate her using it.
Lily Allen – Dr Luke
In 2014, singer Lily Allen must have been going for shocking because she decided to dress up as Dr. Luke, record producer. Now normally, cross-dressing on Halloween wouldn’t be such a shock—however, at the time, singer Kesha had just come forward with sexual allegations against Dr. Luke.
As if the costume wasn’t in enough bad taste, Lily’s name tag read, “Dr. Luke, Gynaecology Dept. As far as we know there was no official apology ever made. Was their bad blood between Allen and Kesha?
Luann de Lesseps – Diana Ross
Real Housewife Luann de Lesseps landed herself in a pot of boiling hot water in 2017 when she attended fellow Housewife, Dorinda Medley’s Halloween party. Indeed, in the episode, another fellow Housewife can be overheard saying that, “Luann’s costume is so disrespectful.”
What set off her fellow castmates? Luann dressed up as Diana Ross, complete with a giant, black afro. The former Countess apologized and said, “I’m horrified! I never meant to hurt anybody’s feelings.”
Ellie Goulding – Native American Chief
In 2014, singer Ellie Goulding made a faux pas by not only dressing as a Native American, but also by posting a now deleted photo of herself on Instagram dressed up with the caption saying, “Chief.” She then posted a second now-deleted photo wearing a large tribal headpiece that included beading and feathers.
Her followers were quick to criticize the star and she quickly deleted the photos. She then defended herself, saying, “I only wore that beautiful unauthentic headpiece for about 5 minutes,” but then also agreed to donate to a Native American charity.
Paris Hilton – Native American
Hmmm… Are we starting to sense a theme here? In 2010, Paris Hilton made headlines on all the weblogs when she arrived at the Playboy mansion Halloween party dressed (or rather partly dressed) as an Indigenous person.
And the internet went crazy! All the blogs lit up with photos, criticizing the heiress for her seemingly racist costume. Paris never made an apology, though. She probably loved the publicity.
Bill Murray – Jimi Hendrix
In 2010, Bill Murray hosted the Crossroads Guitar Festival in Bridgeview, Illinois on June 26th, 2010. Unfortunately, he chose to show up dressed as Jimi Hendrix in full blackface.
Although this took place before celebs were shamed across social media, when the photo of Bill as Jimi did make it’s rounds on the interwebs, the backlash was minimal and many took it in the spirit in which Bill probably intended in the first place.
Nicky Hilton – Native American
Ummm. Like… Duh. Apparently big sister didn’t learn from little sister’s mistake from 2010 because in 2015, Nicky dressed up as a Native American at the 2015 Casamigos Halloween Party.
You would think that with the world becoming more multiculturally diverse and aware that celebrities (who are supposed to be role models) would be a little more sensitive to the subject.
Dwyane Wade – Justin Timberlake
In 2010 Dwyane Wade attended a Halloween party with then girlfriend, Gabrielle Union, in what appeared to be a Justin Timberlake costume. Complete with whiteface makeup.
Surprisingly enough, there didn’t seem to be any resulting backlash nor was there any need for the basketball star to make a public apology. As one Twitter user pointed out regarding this costume, double standards much, Internet?
Colton Haynes – Kanye West and Mahatma Gandhi
Colton Haynes of Teen Wolf fame has a long history of intricate Halloween costumes, sometimes they’re weird, sometimes they’re funny, and sometimes they’re just downright offensive.
In 2011, Haynes thought it would be cute to wear a long, gold chain, black sweat suit, and gold rimmed sunglasses, complete with blackface to dress as Kanye West. Then he turned around the next year and put on blackface again to dress up as Mahatma Gandhi! Celebs just never learn…
Adrianne Curry – Amy Winehouse
Next Top Model contestant Adrianne Curry dressed up as Amy Winehouse for Halloween in 2009. That in itself wouldn’t be very controversial, however; the star also wore a belt wrapped around her arm in tourniquet-style and she also had a fake syringe that she held up to her arm to reference the singer’s drug problems.
Her outfit was completed with a camouflage t-shirt and an outrageous wig. This costume came just two years before Winehouse died of a heroin overdose.
Snooki – Girl on a Milk Carton
Because Snooki isn’t already a controversial reality star, she decided she’d take it a step further and offend parents of missing children everywhere when she decided to dress as a girl on a milk carton.
We’re pretty sure this costume offended every parent who has ever lost a child. Way to go, Snook.
Jason Aldean – Lil Wayne
In 2015, Jason Aldean dressed up as Lil Wayne, complete with blackface, dreadlocks, and bling and headed out on the town in Nashville with a group of friends. The Internet reacted swiftly and angrily.
Eleven months later, the country singer issued an apology that was not an apology at all. “In this day and age people are so sensitive that no matter what you do, somebody is going to make a big deal of it… If that was disrespectful to anyone, I by all means apologize.”