4. Bree Olson

Net worth : $5 million

 This Texas born beauty has made several television appearances, a music video, and was even featured as Penthouse’s Pet of the month. She also posed for Hustler and has a net worth of a staggering $5 million. She shot into the mainstream consciosness after she became a live-in girlfriend of Charlie Sheen during his very public, very bizarre break down a few years back (remember the ‘winning’ memes?). During this relationship she announced plans to retire and she has since moved into mainstream movies; look out for Bree in the horror sequal ‘The Human Centipede 3’ next year.