Most Offensive Celebrity Halloween Costumes: Princess Diana, Nazi Swastika, and Blackface

Not even celebrities are immune to an offensive Halloween costume idea.

Many A-listers have found themselves embroiled in controversy as they have honored the spooky season holiday with stomach-turning outfit choices.

Bill Maher shocked as he dressed up as the late Steve Irwin in 2006 – complete with a fake stingray barb and blood on his chest.

While Julianne Hough donned blackface as she headed out as Crazy Eyes from Orange is the New Black for Halloween 2013.

References to dead celebrities, abuse, racism, and even pedophilia are just some of the touchy suspects referenced with Halloween looks.

Now, Daily Mail takes a look into some of the worst celebrity Halloween costumes ever…

Chloë Sevigny dressed as dead Princess Diana in 1999 

In 1999, actress Chloë Sevigny dressed as a dead version of Princess Diana. 

The beloved former member of the British Royal Family had famously died in a car crash in Paris just two years prior. 

She referenced the accident with a cut on her chin and darkness around both eyes as she used more make-up for a paler complexion. 

If there was any doubt who she was referencing, her beige blazer had ‘Die Di’ written across the lapel.

Bill Maher as dead Steve Irwin in 2006

Comedian and political commentator Bill Maher also went full edgelord by dressing as beloved animal enthusiast and television personality Steve Irwin just one month after his September 2006 death from a stingray attack.

He dressed as ‘The Crocodile Hunter’ with a fake stingray barb protruding from his chest. 

Maher later addressed it on his talk show by saying: ‘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.’

Julianne Hough in blackface as Crazy Eyes from Orange Is The New Black in 2013

One of the most famous examples of an offensive celebrity costume was former Dancing With The Stars pro Julianne Hough channeling Crazy Eyes (played by Uzo Aduba) from Orange Is The New Black. 

Many took offense to her use of blackface, which is the racist practice of using makeup to create a caricature of Black people, which originated in 19th-century minstrel shows and spread harmful, demeaning stereotypes and will be a common theme throughout this list. 

She later apologized for the costume on Twitter (now X) as she said: ‘It certainly was never my intention to be disrespectful or demeaning to anyone in any way. 

‘I realize my costume hurt and offended people and I truly apologize.’

 Khloe Kardashian as a pimp with four black women in 2003

Khloe Kardashian once dressed as a pimp in 2003 as she was joined by her black friends – twins Malika and Khadijah Haqq, actor Meagan Good, and Good’s sister La’Myia Good.

Her friend sported apparent dog collars  while dressed in lingerie, while Kardashian held onto chains connected to them.

Kardashian has never addressed the costume but Meagan did in 2019 as she wrote: ‘That one time on Halloween when you were young and dumb. 

‘And clearly didn’t think 15 years ahead lol smh. Welp, mistakes were made.’

Emily Hampshire and a friend dressed as Johnny Depp and Amber Heard in 2023

Schitt’s Creek star Emily Hampshire and a friend dressed as Johnny Depp and Amber Heard just a year after their defamation case – sparked by Heard’s claims that Depp had abused her. 

The photos from the Instagram post showed Hampshire holding a bottle of wine as their friend channeled Heard with an upset face. 

The post was later deleted and Hampshire issued an apology. They wrote: ‘I am deeply sorry and ashamed for putting something that awful out in the universe. Domestic abuse is never, ever funny.’ 

Depp  famously lost the libel action which he brought at the UK High Court in 2020, after being called a ‘wife beater’, but successfully brought a libel action against Amber in a US court in 2022. (The jury also ruled with Heard on one of her three countersuit claims, finding Johnny’s lawyer had defamed her in that instance).

As a result of the controversy, Johnny’s reputation took a battering with his stock as one of the world’s leading actors dramatically falling amid sensational headlines of domestic abuse, sexual violence, drug taking and excessive drinking.

Adrianne Curry as Amy Winehouse with a syringe in 2011 

Unlike the previous two cases of people dressed like dead celebrities, model and television personality Adrianne Curry channeled Amy Winehouse before her death.

However, she referenced Winehouse’s drug and alcohol issues by pretending to shoot up with a fake syringe. 

Winehouse died of alcohol intoxication less than two years later in July 2011.

Tana Mongeau as sexy Jojo Siwa ( who was 15 at the time) in 2018 

YouTube star Tana Mongeau dressed as a sexualized version of Jojo Siwa in 2018, however, the influencer was only 15-years-old at the time. 

Tana wore a pink bra and thon, blue ribbons, with Siwa’s signature hair ribbons in a post she captioned: ‘HOE HOE SIWA.’ 

If that wasn’t enough she even tagged the Dance Moms star. 

Tana later addressed the controversy to her fans as she wrote: ‘hey guys! saw some tweets about my Jojo costume and I just wanna clarify before things get crazy- Jojo is a great friend of mine & I would never intend to sexualize HER, I literally think that anything like that is gross as f***.’ 

Gwen Stefani in Hurricane Sandy costume in 2014

No Doubt frontwoman Gwen Stefani is the only person on this list who was torched for poking fun at a natural disaster. 

She referenced 2012 tropical cyclone Hurricane Sandy which killed over 200 and devastated the Caribbean. 

She was dressed as a pun to the name by wearing a costume of Sandy from 1978 classic Grease with a bloody headwound to reference the hurricane.

Harry Hamlin wearing swastika T-Shirt as Sid Vicious in 2015 

Harry Hamlin and his wife Lisa Rinna publicly apologized after Hamlin dressed as Sid Vicious – complete with a Nazi swastika shirt in 2015.

Posing as the late bassist of The Sex Pistols, who was accused of murdering his girlfriend Nancy Spungen – the couple were quickly put on blast.

Rinna later posted an apology on Instagram as she wrote: ‘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.’ 

Spungen was found stabbed to death in a NYC hotel room in October 1978. 

Vicious claimed that he had killed her before recanting his confession and saying he didn’t remember what happened. 

He later died from an overdose aged just 21 after being released on bail.

Billie Eilish and Jesse Rutherford in age gap costume in 2022 

In 2021, Billie Eilish and then-boyfriend Jesse Rutherford found themselves in hot water as they playfully referenced the age gap in their relationship. 

Eilish was 20 at the time and Rutherford was 31 so they faced plenty of criticism over their age gap – including the fact that he had known her since she was 15 – by fans. 

They tried to poke fun of this with their Halloween costumes as Eilish dressed as a baby and Rutherford donned the look of a much older man.

Jeff Ross as Joe Paterno with football players wearing towels in 2012

Comedian Jeff Ross showed up to the Comedy Central Roast Of Roseanne Barr as controversial college football coach Joe Paterno. 

As if that wasn’t grim enough, he was joined by two men who wore nothing but football helmets and towels. 

Paterno’s career ended a year before in 2011 as the result of the Penn State child sex abuse scandal. 

His assistant coach Jerry Sandusky was indicted on 52 counts of child molestation, stemming from incidents that occurred between 1994 to 2009. 

Sandusky was ultimately convicted on 45 counts of child sex abuse in June 2022.

Chris Brown as member of Taliban in 2012

Chris Brown attended Rihanna’s Halloween party seemingly dressed as a member of terrorist organization Taliban. 

He never addressed the backlash personally but his mother later posted on Twitter (now X): ‘HALLOWEEN IS FOR FUN NOTHING MORE THAN JUST FUN. GET A LIFE PLEASE.’

OJ Simpson as a gynecologist named Seymour Bush

This is a rare occurrence where a celebrity’s offensive costume may not be among the worst things that they were accused of.

In 2018, a released-from-prison OJ dressed as a gynecologist with a name tag that read ‘Dr. Seymour Bush’ at a costume party in Las Vegas.

Simpson was found guilty in 2007 after he robbed a memorabilia dealer at gunpoint.

The Naked Gun star was sentenced to 33 years behind bars, but was released on parole after just nine. 

Simpson’s prison sentence came around 13 years after he was acquitted for the double-murder of his ex-wife Nicole Brown Simpson and her friend Ron Goldman.

Shaun White as Simple Jack in 2018

Newly-single Shaun White courted controversy in 2018 as he channeled Tropic Thunder character Simple Jack. 

Simple Jack is a fictional character with intellectual disabilities within the comedy film as portrayed by Ben Stiller. 

White was called out by Special Olympics and he later apologized to them by posting: ‘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.’

Ashley Benson as Cecil The Lion in 2015 

Ashley Benson was blasted on social media as she dressed as Cecil The Lion for an advertisement. 

The lion was named in the original post but it was later edited before the post was ultimately deleted. 

Cecil The Lion was killed in July 2015 by American dentist and trophy hunter Walter Palmer in Zimbabwe’s Hwange National Park and stirred up plenty of controversy at the time. 

She later tried to deny that it referenced the slain animal as she wrote: ‘Yesterday’s post was in poor taste and I absolutely regret all of the hurt that photo caused. 

‘My costume was not Cecil the Lion, when I saw that, I contacted my management who handled the post and had it immediately changed.’

Heidi Klum as Hindu goddess Kali in 2008 

Heidi Klum is considered the ‘Queen of Halloween’ by many as she has thrown a star-packed party every year with her outfit always being the most intricate. 

However, in 2008 she dressed as Hindu goddess Kali who symbolizes death and time, along with doomsday, sexuality, and violence, along with maternal instincts and love. 

The outfit had stirred up controversy among many, especially Hindu people. She has never addressed the controversy.

And Heidi is far from the only famous face accused of cultural appropriation and/or being racially insensitive at Halloween – see the full rundown below…

Justin Trudeau in brownface in 2001 

Kate Hudson and friends as Bhagwan Shree Rajneesh and followers (as referenced in 2018 Netflix documentary Wild Wild Country)

Colton Haynes in brownface as Gandhi in 2012

Colton Haynes in blackface as Kanye West in 2011

Luann de Lesseps in blackface as Diana Ross in 2018 

 Jason Aldean in blackface as Lil Wayne in 2015

Joni Mitchell using blackface as a black man for a Halloween party in 1976 

Hilary Duff as a pilgrim and Native American in 2016

Nicky Hilton as Native American in 2015

Chrissy Teigen and John Legend as cowboy and Native American in 2008 

Tia Mowry as a geisha in 2013