David Gest – $20,000

David Gest was not just a well-known comedian and entertainer, but he was also a television personality who was a contestant on the reality show Celebrity Big Brother. Aside from that, he made quite a lot of high-profile friends who helped him get a taste of what it was like to be in the limelight. One of them was Michael Jackson, whom he considered as his long-time friend. As a matter of fact, it was the singer who encouraged him to undergo cosmetic surgery so that he will always look his best.

He was also married to Liza Minelli. Although their relationship was short lived, Gest did not make too much fuss about it and remained down to earth through it all. He did later regret having to spend most of his investment money on altering his body, which he mentioned in interviews.