20 Celebrities Who Sparked Controversy With Their, Umm, “Questionable” Halloween Costume Choices

People are obsessed with finding the perfect Halloween costume and yet oftentimes Halloween costumes still go terribly wrong. Despite their exalted social status this is even true for celebrities, who face a much larger and harsher spotlight than regular people. Some celebrity Halloween costumes are great while others are a great big yikes. Whether it’s a simple matter of Halloween costume fails or of straight-up racist Halloween costumes, here are a few celebrity Halloween costumes that missed the mark…or worse. 

1. Bill Maher as the recently deceased Steve Irwin (2006)

2. Paris Hilton as a Native American (2010)

3. Chris Brown as a terrorist (2012)

Chris Brown dressed as a terrorist LOOOOOOOOOOL #halloweenswag pic.twitter.com/aNeEelWe

— Mon (@Monika_S07) November 3, 2012

4. Shaun White as “Simple Jack” from Tropic Thunder (2018)

5. Julianne Hough as “Crazy Eyes” from Orange Is The New Black (2013)

@KatieGeorge2 Non-PC would be bringing up that time that Julianne Hough wore blackface for Halloween. #GreaseLive pic.twitter.com/K9XV90Gx3t

— Libby Jones (@libbyjones715) February 1, 2016

6. Heidi Klum as the Hindu goddess Kali (2008)

Heidi Klum as Kali is still one of the best Halloween costumes ever worn pic.twitter.com/NjzLu6wNMw

— Rikh (@rikhalicious) October 31, 2014

7. Hilary Duff and her boyfriend as a Pilgrim and Native American (2016)

Hilary Duff and her boyfriend got major backlash for their Native American and pilgrim couple costume. https://t.co/bgY3yadH68 pic.twitter.com/loQAq7UVSY

— The Insider (@TheInsider) November 1, 2016

8. Pretty Little Liars’ Ashley Benson as Cecil the Lion (2015)

9. Jeff Ross as Joe Paterno (2012)

WOW!!! #SMH :’-D RT @Sibulele_Q HAHA Jeff Ross attended the Roast of Rosanne Barr dressed as Joe Paterno :’D cc @__Senz pic.twitter.com/oGTgk9n2

— Corcho (@Big_Corcho) August 5, 2012

10. Chrissy Teigen as a Native American (2008)

@Google Remember when Chrissy Teigen insensitively and disrespectfully dressed like a Native American and now you are using her for promotion? pic.twitter.com/ZQ337sfMb3

— Nolan (@station3248) June 21, 2018