Sinbad
There was a time when Sinbad seemed to be the comedian who had it all. His role on the sitcom A Different World made him a mainstream stream, and with it the chance for financial success.
Unfortunately, things didn’t quite work out in his favor. The man has now declared bankruptcy multiple times, with business expenses being the main reason for his issues. He was reportedly $11 million in debt back in 2013, and he couldn’t pay it off because he was never making more than $16,000 a month.
Tionne ‘T-Boz’ Watkins
TLC was responsible for some major hits in the ‘90s, including Waterfalls, No Scrubs, and Unpretty. Unfortunately, while their songs and albums might have been million-sellers, the group’s members never saw much financial success.
That was largely down to their management, although the blame isn’t solely on them. One of the reasons that T-Boz has filed for bankruptcy multiple times is because she buys things like homes worth a million dollars. It was the mortgage payments for this luxury residence that forced her to turn to bankruptcy in 2011.