4. Flavor Flav
Appeared on: The Surreal Life, Season 3 (2004); Strange Love (2005); Flavor of Love (2006-2008)
Though it's been a long time since Public Enemy was a cultural force, we're not entirely sure how to feel about a rapper who participated on It Takes a Nation of Millions to Hold Us Back transitioning into a reality star on a show where 20 tequila-guzzling women fought over his affection. Nevertheless, it was certainly a profitable move for him. Not to mention for VH1, a network that might've still been playing Pop Up Video all day if not for Flav's string of reality hits.