Even the world’s most famous people can go flat broke. It’s one of the most fascinating contradictions in celebrity culture: how someone can earn tens or even hundreds of millions of dollars—often in just a few short years—and still wind up bankrupt. For some, the collapse happens suddenly after a bad investment or an expensive divorce. For others, it’s a slow burn of poor financial advice, unpaid taxes, or a lifestyle that simply outpaces reality. Whatever the cause, bankruptcy among celebrities has always captivated the public because it shatters the illusion that fame equals financial security.
From boxing legends and pop icons to Oscar winners and major-league athletes, the stories of celebrity financial ruin are as dramatic as any Hollywood script. A few were truly blindsided—caught in tax nightmares, lawsuits, or mismanagement by trusted advisors. Others lived like money would never run out, buying private islands, castles, and fleets of exotic cars, only to learn that even endless paychecks can dry up. Some of these stars eventually bounced back, using bankruptcy as a strategic reboot. Others never recovered, becoming cautionary tales of how fast fortune can turn to dust.
In this roundup, we look at 15 of the most striking examples of celebrities who went broke or declared bankruptcy. And because not everyone actually filed, we’ll also spotlight a few who came dangerously close—those who dodged bankruptcy by sheer hustle, lucky breaks, or the help of very generous friends.
50 Cent
In 2015, rapper Curtis “50 Cent” Jackson shocked fans by filing for Chapter 11 bankruptcy. Despite at one point once boasting a net worth near $100 million, he claimed $36 million in debt against less than $20 million in assets. The filing came after a series of costly lawsuits, including a $7 million judgment tied to a leaked sex tape. A court-approved plan allowed him to repay roughly $23 million and emerge debt-free by 2017. His case became a modern example of how even the savviest entrepreneurs can overextend.
Mike Tyson
Mike Tyson earned an estimated $400 million during his boxing career, only to lose nearly all of it. Lavish homes, luxury cars, pet tigers, and a $9 million divorce settlement drained his fortune. In 2003, Tyson filed for bankruptcy with $23 million in debt, including $13 million owed to the IRS. Once the most feared man in boxing, “Iron Mike” became a symbol of how extravagance and poor management can destroy even astronomical earnings.
Christian Petersen/Getty Images
MC Hammer
At his peak in 1990, MC Hammer made $33 million in a single year—but he also supported an entourage of over 200 people and spent millions on mansions, horses, and sports cars. When the money dried up, Hammer filed for bankruptcy in 1996, reporting about $1 million in assets and more than $10 million in debt. He later said much of his money went toward helping his community, but the result was the same: a fortune gone and a humbling financial reset.
Justin Sullivan/Getty Images
Toni Braxton
Despite selling over 67 million records, Toni Braxton filed for bankruptcy twice—first in 1998, then again in 2010 after health issues canceled her Las Vegas residency. Her second filing listed debts of up to $50 million. Braxton lost the rights to several of her hit songs, including “You’re Makin’ Me High,” before rebuilding her career through touring and reality television.
Kim Basinger
Oscar winner Kim Basinger filed for bankruptcy in 1993 after being hit with an $8.1 million judgment for backing out of the film “Boxing Helena.” Facing financial ruin, she sought Chapter 11 protection and later settled the case for $3.8 million. The bankruptcy nearly ended her career, but Basinger rebounded with “L.A. Confidential” four years later—and an Academy Award.
Cyndi Lauper
Before becoming a pop icon, Cyndi Lauper was broke. Her early band, Blue Angel, flopped, and after being sued by their manager, she filed for bankruptcy in 1981, unable to pay roughly $80,000 in debt. Lauper worked retail and sang in restaurants to survive until her solo debut, “She’s So Unusual,” turned her into a superstar two years later.
Larry King
Before his decades-long run on CNN, Larry King was accused of misusing $5,000 from a business partner—a scandal that wrecked his finances. By 1978, he owed $350,000 and filed for bankruptcy. Ironically, that same year, he landed a new radio gig that evolved into “Larry King Live,” making him one of TV’s most successful hosts.
Francis Ford Coppola
The “Godfather” director filed for bankruptcy twice, most notably in 1992 after his passion project “One from the Heart” flopped. The film cost $27 million but earned only $4 million, leaving Coppola with $98 million in liabilities. He later reinvented himself as a winemaker and hotelier, proving even Hollywood legends can start over. Unfortunately, Hollywood legends can also make the same mistakes again, as Francis did with his passion project “Megalopolis.” Francis infamously sold off his wineries and other businesses to self-finance the project. He spent $120 million, mostly of his own money. The film made $14 million and rendered Francis Ford Coppola “broke” and forced to sell belongings to raise cash in late 2025.
Curt Schilling
Curt Schilling earned $114 million during his career but lost his fortune after investing more than $50 million into a failed video game company, 38 Studios. When the company collapsed in 2012, Schilling was forced to sell his home and memorabilia, including his “bloody sock.” He didn’t personally file bankruptcy, but the company’s collapse wiped him out financially.
Nick Laham/Getty Images
Michael Jackson
Despite earning hundreds of millions, Michael Jackson spent far more—on Neverland Ranch, art, and endless luxury. By 2007, he was unable to repay a $25 million loan and was reportedly $500 million in debt when he died in 2009. While he never formally declared bankruptcy, his lavish lifestyle and lawsuits left him “technically bankrupt” in his final years.
Burt Reynolds
In 1996, Burt Reynolds filed for bankruptcy after a string of bad investments and an expensive divorce from Loni Anderson. He was over $10 million in debt, forced to sell homes, cars, and even a private jet. Reynolds later joked that his biggest regret was “not spending even more money,” turning his downfall into part of his legend.
Gary Busey
Gary Busey filed for Chapter 7 bankruptcy in 2012, listing less than $50,000 in assets and up to $1 million in debts. Years of inconsistent work, medical bills, and back taxes had caught up to him. He later found a second act in reality TV, making light of his struggles on shows like “Celebrity Apprentice.”
Gary Coleman
The “Diff’rent Strokes” star earned millions as a child actor but sued his parents for mismanaging his trust fund. By 1999, he filed for Chapter 7 bankruptcy with $72,000 in debt. Gary Coleman never recovered financially, working odd jobs and making occasional TV appearances until his death in 2010.
Meat Loaf
After his 1977 megahit “Bat Out of Hell,” Meat Loaf went bankrupt in 1983 following lawsuits and a flop follow-up album. He later made a triumphant comeback in the 1990s with “Bat Out of Hell II” and “I’d Do Anything for Love,” proving bankruptcy doesn’t have to end a career.
Honorable Mentions: Celebrities Who Came Close
Nicolas Cage burned through $150 million buying castles, islands, and exotic pets before owing $14 million in back taxes. He avoided bankruptcy by working nonstop in dozens of films.
Willie Nelson owed the IRS $32 million in back taxes in 1990, prompting asset seizures and auctions. He refused to file bankruptcy, instead recording “The IRS Tapes: Who’ll Buy My Memories?” to pay off the debt.
Sarah Ferguson, Duchess of York faced up to $8 million in debt by 2010 and was caught offering to sell access to Prince Andrew. With help from wealthy friends, she narrowly avoided bankruptcy and later rebuilt her image through media projects.
