Show: The Apprentice, The Surreal LifeCelebrity Apprentice: All Stars
Years Active: 2004-present
Most Villainous Moment: Pouring a glass of wine on Piers Morgan's head (Celebrity Apprentice Season 7, Episode 6) 

Omarosa’s villainous reputation precedes her—even if you never watched the first season The Apprentice or one of the several other reality shows she appeared on afterwards, you know her. She considers her harsh behavior simply the nature of business, but we can’t really see the business value in dumping a glass of wine on Piers Morgan’s head (although I totally get it). She made enemies with her fellow contestants at just about every turn, and had a talent for getting under people’s skin and manipulating them into looking like the bullies. For example, Omarosa pushed LaToya Jackson so far on a season of Celebrity Apprentice that Jackson commented, “Omarosa’s fiance passed away not long ago. He had a heart attack—I’m sure she gave it to him.” Even though Omarosa's reality TV days may be behind her, we’re confident she’ll continue to piss America off now that she’s President-elect Donald Trump’s director of African-American outreach. Yep. That’s real life. —Lauren Zupkus