Money Woes of the Rich and Famous: 11 Celebrities Who Filed for Bankruptcy

Bankruptcy is a financial nightmare that can affect anyone, even the rich and famous. Despite their often lavish lifestyles and staggering earnings, numerous celebrities have faced hefty financial difficulties, with many having no other option than filing for bankruptcy. This unfortunate turn of events also highlights the hidden financial struggles behind the glamour and fame — where mismanagement, poor investments, and excessive spending can quickly erode even the largest of fortunes. 

From Oscar-winning actors and singers to rappers and entrepreneurs, here are 11 celebrities that have faced this daunting reality in recent years.

The acclaimed boxer filed for bankruptcy in 2003 after earning over $300 million throughout his career. His financial downfall was due to a combination of legal issues, extravagant spending, and poor financial decisions. Despite his impressive earnings, Tyson's lavish lifestyle, which included expensive homes, cars, exotic pets, and a large entourage, quickly drained his fortune. He had $23 million in debt.

Tyson also faced multiple legal battles and costly divorce settlements that further exacerbated his financial problems.

Toni Braxton, an award-winning R&B singer known for hits like "Un-Break My Heart," and "Hit the Freeway," filed for bankruptcy twice — first in 1998 and again in 2010. Braxton's financial struggles were primarily attributed to health issues, which impacted her earning potential and led to hefty medical bills. According to a law firm, Braxton's outstanding debts amounted to "somewhere from $10 to $50 million."

Despite her initial success in the music industry, disputes with her record label and poor financial management further complicated her financial situation. 

Despite being one of the most famous actors in the world, Nicolas Cage found himself in deep financial troubles around 2009. Cage's financial woes were driven by his extravagant spending on items such as private islands, exotic animals, and rare artifacts, which led to enormous debt. His lavish spending habits, combined with tax problems, forced him to sell many of his assets and drastically downsize his lifestyle. 

At one point, Cage admitted having to take on "crummy" acting roles that "didn't work" just to pay off his debts. The Academy Award-winning actor is best known for films like "Leaving Las Vegas," "Face/Off," and "National Treasure."  

Related: Celebs Who Blew Their Money on Stupid Things

Curtis James Jackson III, better known as 50 Cent, is a rapper, actor, and entrepreneur. But despite having successful careers in music and business, 50 Cent filed for bankruptcy in 2015 as he faced legal judgments amounting to millions of dollars. His financial troubles were exacerbated by lavish spending and costly lawsuits, ultimately spurring Jackson to file for bankruptcy as a means to manage the debt. 

50 Cent has since diversified his career, becoming an executive producer and actor on the hit TV show "Power" and its spin-offs. He's also ventured into various new business endeavors, including partnerships and real estate investments.

Related: Falling Stars: Famous Public Meltdowns By Celebrities

Cyndi Lauper, a singer and actress known for chart-topping hits like "Girls Just Want to Have Fun," "Time After Time, and "What's Going On," faced financial turmoil early in her career. Before her rise to fame, Lauper filed for bankruptcy in 1981 following the breakup of her band, Blue Angel, in which the manager reportedly sued her for a breach of contract. The dissolution of the band and subsequent career setbacks rendered her financially unstable for several years. 

But Lauper eventually overcame the financial hurdles as her solo career flourished, bringing her much of the success and recognition that she still enjoys to this day. 

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The reality TV star, best known for her role in "The Real Housewives of New Jersey," filed for bankruptcy in 2009. After Giudice and her ex-husband Giuseppe “Joe” were found guilty of fraud, they had to pour sizable funds toward restitution and legal fees. Their fraudulent activities, combined with a lavish lifestyle, resulted in overwhelming debt that the family could not manage. 

Since then, Giudice has worked to rebuild her life and finances by returning to television, and starting new business ventures with now-husband Luis Ruelas.

Related: 27 Big Celebrities Who've Had Tax Trouble

Known for films like "The Usual Suspects," and for being part of the famous Baldwin family, Stephen is no stranger to money problems. After filing for bankruptcy in 2009,  Baldwin's financial struggles, which stemmed from unpaid taxes and mortgage payments, led to the foreclosure of his home. Poor financial management and the failure to pay taxes also contributed to his financial collapse.

Today, Baldwin remains active in the entertainment industry but maintains a lower-profile compared to his earlier years. Perhaps Baldwin's ultra-successful daughter and son-in-law (Hailey and Justin Bieber) could also help him out. 

Related: Celebrities That Have Their Own Private Planes

Gary Busey, an actor known for his roles in "The Buddy Holly Story" and "Lethal Weapon," filed for bankruptcy in 2012 after claiming more than $500,000 in debt. Busey's financial troubles were largely due to mounting medical bills and poor financial decisions. A serious motorcycle accident, which led to a brain injury, coupled with subsequent health issues, left him with sky-high medical expenses and inconsistent work opportunities, he said at the time. 

Since then, Busey has appeared in various television shows and films, including popular reality TV shows like "Celebrity Apprentice" and "Dancing with the Stars."

Though the King of Pop never formally filed for bankruptcy, he still faced severe financial distress before his death in 2009. Despite his immense earnings, Jackson's extravagant lifestyle, legal battles, and expensive habits led to massive debt — to the tune of $400 million to $500 million. Lavish spending on maintaining Neverland Ranch and ongoing legal issues also further drained his financial resources.

Jackson is known for chart-topping hits like "Thriller," "Man in the Mirror," and "Billie Jean." Today, he is still widely considered one of the greatest entertainers of all time, with a profound influence on music, dance, and popular culture.

Known for his role in "The Partridge Family," Cassidy filed for bankruptcy in 2015 due to mounting debt totaling over $10 million. The former actor and singer, who was once known as a heartthrob, attributed his financial woes to health issues and declining career opportunities. His financial troubles were further exacerbated by alcoholism, medical expenses, and failed marriages.

Cassidy died in 2017 at the age of 67. His son, Beau Cassidy, inherited the bulk of his estate, which included assets totaling upward of $1.68 million.

Tia Carrere, an actress and singer known for her roles in "Wayne's World, "General Hospital," and for voicing Nani in "Lilo and Stitch," filed for Chapter 11 bankruptcy in March 1986. Though Carrere claims her financial difficulties stemmed from legal battles and a decline in acting opportunities, some believe she filed for bankruptcy in an attempt to get out of her contract with "General Hospital," and star in another show. 

Today, Carrere remains active in Hollywood by balancing her acting and singing career with various charitable endeavors.