American stand-up comedian Sinbad became famous back in the ’90s thanks to his HBO specials, his guest appearances on several TV shows, and his roles in films like ‘Necessary Roughness’, ‘Good Burger’, ‘Houseguest’, ‘First Kid’, ‘Jingle All the Way’, and others. However, he pretty much stopped after that.
Not only was Sinbad barely working, he got slammed with a tax bill of $8 million, which forced him to mortgage his house and file for bankruptcy. Yikes!
T-Pain
American rapper T-Pain saw huge success after his second album, 'Epiphany', reached No. 1 on the US Billboard 200 chart. He saw massive success in the following years, releasing a number of hit singles and even winning two Grammy Awards. The rapper even had his own record label, and everything was going great until a series of terrible spending habits and bad investments nearly left him and his family on the street.
As the rapper himself said in an interview, he went from having $40 million in the bank at the peak of his career, to " having to borrow money to get my kids Burger King." Fortunately, T-Pain seems to have learned his lesson, since he is now doing much better with his finances, releasing new songs, and even won the first season of "The Masked Singer", a reality show on Fox.
Michael Jackson
The King of Pop is said to have been in terrible debt when he died in 2009, and by terrible we mean well over $400 million. Before his sudden passing, Michael Jackson was about to foreclose his infamous 'Neverland' home.
Even though Jackson was once one of the wealthiest people in the world, an unseemly amount of spending resulted in him having to take out loans that he couldn't ever pay back. His situation only got worse after he was part of a number of very expensive lawsuits in his later years. However, almost seven years after his death, the debt was completely turned around after his billion-dollar estate was sold in 2012.
Mickey Rooney
Even though Mickey Rooney is known as a famous actor, comedian, producer, and radio personality, he actually filed for bankruptcy way back in the 1960s. And hey, if you have a career spanning nine decades, it makes sense to have a few run-ins with money.
Many people don't know that Rooney spent a huge part of his career trying to recover from his dire financial situation. Clearly, this star spent his younger years having way too much fun and spending way too much money, having just $500 to his name at one point. Thankfully, he'd managed to fully recover by the time he passed away, in 2014.
Ed McMahon
The beloved TV personality Ed McMahon was a household staple back in the '50s and '60s. McMahon was a TV announcer, comedian, actor, singer, and famous game show host, catapulting to fame with the ABC show, "Who Do You Trust?". The game show, which he hosted with legendary Johnny Carson, ran from 1957 to 1962. And then, McMahon went on to host another famous game show with Carson, NBC's "The Tonight Show Starring Johnny Carson", until 1992.
Needless to say, this American entertainer amassed quite a fortune throughout the years. However, McMahon couldn't hold on to his millions, and lavish spending habits got Ed in a pretty tight situation with lenders. A $4.8 million home loan left him almost broke by the time he passed away, in 2009.