7. Sinbad ($-11 million)
Comedian and actor Sinbad, is known for awful films that are memorable due to the fact that many of us get nostalgic about the 90s. Coneheads (1993), First Kid (1996), Jingle All The Way (1997) and Good Burger (1997) are in no way, shape or form Oscar worthy, but Sinbad still made a good living for himself. Despite having consistent work since the early 90s, Sinbad has filed for bankruptcy on two separate occasions, the most recent being in 2013. He reportedly owes debts of $11 million, $8 million of which stems from back taxes.
In spring of 2013, Sinbad opened up to Oprah Winfrey about his financial situation stating, “I didn’t buy Bentleys. I didn’t live large. I invested in me. I invested in a lot of other people. I would not change it; I would not go back.” Although he has no regrets, Sinbad’s investments in himself and other people have left with a net worth of -$11 million.