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.
Sinbad
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!
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.
Isaac Hayes
The soul, funk, disco and rock 'n' roll legend Isaac Hayes was huge back in the 1960s. Hayes was one of the creative powerhouses behind Stax Records, a famous Southern soul music label. Although he made a killing back in the '60s, this Rock and Roll Hall of Famer had to file for bankruptcy in 1976 after a whopping $6 million debt in taxes.
Hayes won three Grammys, one Golden Globe Award for Original Score and one Academy Award for Best Original Song for the 1971 cult film, 'Shaft'. By 1977, in an interview with Ebony Magazine, Hayes said that his money problems came from mismanaging his record label, insane spending and just generally placing "too much trust in people". Still, Hayes kept making music, wrote a successful cookbook and owned two restaurants by the time of his death, in 2008.
David Cassidy
David Cassidy had an extremely successful acting and singing career back in the '70s and '80s. Catapulted to fame by his role as Keith Partridge in the famous TV show 'The Partridge Family', David was already known around the country and used this to start a career in music.
In 1970, his hit song "I Think I Love You" reached number one on the Billboard Hot 100 chart, and the teen idol was on top of the world. Unfortunately, as it often happens with these stars, Cassidy went bankrupt in 2015, after being in debt for $10 million. A long history of DUIs, alcohol abuse, and a costly divorce in 2014 forced Cassidy to auction off his mansion. Sadly, he died from liver and kidney failure in 2017.