Some of the most famous celebrities who went broke did it at the height of their fame, and some of the richest names in entertainment had almost nothing before they made it. 50 Cent, MC Hammer, Mike Tyson, Toni Braxton and TLC all filed for bankruptcy after selling millions of records or earning hundreds of millions of dollars. Tyler Perry and Steve Harvey were homeless before they built their empires.
50 Cent
In May 2015, Forbes estimated 50 Cent’s net worth at $155 million. Two months later, he filed for Chapter 11 bankruptcy, a type of filing that lets a person or business keep operating while reorganizing their debts under court supervision. He listed both his assets and his liabilities in the range of $10 million to $50 million. The filing came days after a court ordered him to pay $5 million in a lawsuit over a sex tape he posted online.
He agreed to repay about $23 million in debts over five years and kept building. In 2018, he signed an overall deal with Starz reportedly worth up to $150 million, fueled by the success of Power. For 50, bankruptcy was a way to restructure debt, not a sign he was out of money.
MC Hammer
At his peak, MC Hammer reportedly earned $33 million in a single year. He bought a mansion in Fremont, California, for $12 million, spent another $30 million customizing it, and carried a staff of about 200 people.
By 1996, he had filed for bankruptcy with roughly $14 million in debts, and the mansion eventually sold for around $5.3 million. Hammer reinvented himself in Silicon Valley, becoming an early investor in Square and backing Bump, an app Google later acquired.
Mike Tyson
Mike Tyson earned more than $300 million over his boxing career. For his 2002 fight against Lennox Lewis alone, he was guaranteed $17.5 million plus a cut of pay per view. One year later, he filed for bankruptcy, reportedly owing about $23 million.
It took more than a decade and a trip through rehab to get his life and finances back on track. His scene stealing role in The Hangover in 2009 introduced him to a new generation. He launched the cannabis brand Tyson 2.0 and a podcast, and he returned to the ring against Jake Paul in 2024, reportedly earning about $20 million.
Toni Braxton
Toni Braxton was one of the biggest R&B stars of the ’90s, selling 25 million albums that decade. “Un-Break My Heart” spent 11 weeks at No. 1. She still filed for bankruptcy in January 1998 after a legal fight over her recording contract.
In 2010, she filed again, listing debts between $10 million and $50 million after health problems forced her to step away from her Las Vegas residency. Each time, she rebuilt. In 1998, she became the first Black actress to play Belle in Beauty and the Beast on Broadway. Braxton Family Values premiered in 2011, and she settled her second bankruptcy case in 2013. Six months later, she bought a $3 million home in Calabasas.
TLC
TLC’s money was there. It just wasn’t going to them. CrazySexyCool became the first album by a female group certified diamond, meaning more than 10 million copies sold in the U.S. On July 3, 1995, the trio still filed for Chapter 11 bankruptcy with about $3.5 million in debts.
Their recording deal paid the group 56 cents per album, split three ways, before expenses were taken out. That left each member taking home less than $50,000 a year.
TLC renegotiated its contracts and paid $3 million to own the TLC name. FanMail debuted at No. 1 in 1999, selling 318,000 copies in its first week, and won the Grammy for Best R&B Album. In 2015, T-Boz and Chilli asked fans for $150,000 on Kickstarter to fund their final album and raised more than $430,000.
Broke Before the Bag
Tyler Perry and Steve Harvey never filed for bankruptcy. They struggled to afford basic necessities before they ever got famous.
Tyler Perry
Tyler Perry saved $12,000 working jobs like bill collector to stage his first play, I Know I’ve Been Changed. It flopped. He kept quitting jobs to keep working on the play and ended up homeless, living in a Geo Metro for about three months while hiding it from the repo man.
In 2020, Forbes estimated his fortune at $1 billion. That included $320 million for his content library, which he owns outright, $300 million in cash and investments, $280 million for Tyler Perry Studios, $60 million for his stake in BET+, and $40 million in homes and other assets. Those figures reflect Forbes’ 2020 valuation, not his current holdings.
Steve Harvey
Before Steve Harvey became a household name, he spent nearly three years in the late 1980s living in his Ford Tempo. He has described surviving on as little as $50 a week, keeping his food in an Igloo cooler and washing up at gas stations while chasing comedy gigs.
Today, he hosts Family Feud and Judge Steve Harvey, runs a weekday radio show, and has a business portfolio that includes books, a clothing line and investments. His net worth has been estimated at around $200 million, though that figure isn’t publicly verified.
