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1. Chelsea Handler

50 Cent’s ex-girlfriend is most famous for putting her foot all the way in her mouth when it comes to race relations. Aside from tweeting a can of grape soda at Nick Cannon during their one-time “Twitter beef,” the “comedienne” has been constantly called to the carpet for her countless racially insensitive remarks. But her most recent gaffe was courtesy of last year’s Oscars, when she took over the Huffington Post’s Twitter account and began live-Tweeting during the broadcast. She made countless remarks about Lupita N’yongo (“Angelina Jolie’s adoption papers went through”) and the movie 12 Years a Slave…all to promote her book, Uganda Be Kidding Me, which was a collection of essays about Chelsea and other clueless white women traveling through Africa (specifically, Uganda). In response to the backlash, Chelsea remarked that the slights against the Kenyan actress were to promote the book (because every country in Africa is exactly the same, AMIRITE?!), and claimed that she wasn’t a racist “because she dates a lot of black people.” So, yeah. There’s that.

Talk to Bernadette Giacomazzo on Twitter at @berngiacomazzo and on Instagram at @kbprfirm.

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