Celebs Who Lost Their Entire Fortune and Had to Start Over

It’s easy to be captivated by the glamorous lives of celebrities and the immense wealth they often enjoy. However, many stars actually lose their fortunes due to bad money habits or unexpected problems. Even famous actors and musicians can face bankruptcy and significant debt. Getting back on their feet usually means starting over and learning tough lessons about managing finances. These experiences demonstrate that simply earning a lot of money isn’t enough to guarantee financial security.

MC Hammer

MC Hammer, famous for his hit song ‘U Can’t Touch This,’ earned over thirty million dollars but quickly spent it on things like a large staff and a luxurious home. Declining album sales and legal issues added to his money problems, leading him to file for bankruptcy in 1996 with significant debts. Later, Hammer successfully changed careers, becoming a tech investor and social media advisor to rebuild his life and finances.

Mike Tyson

Mike Tyson made a fortune – hundreds of millions of dollars – as a professional boxer. However, he spent lavishly on things like expensive cars and rare animals, and faced significant costs from legal issues and his divorce. By 2003, his finances were in trouble, and he filed for bankruptcy owing $23 million. Since then, he’s worked to rebuild his wealth through comeback fights, acting appearances – including in the movie ‘The Hangover’ – and now a thriving cannabis business, as well as hosting a popular podcast.

Nicolas Cage

Nicolas Cage was once a very wealthy actor, earning around $150 million. He famously spent his money on unusual purchases like dinosaur skeletons, private islands, and castles in Europe. However, he faced a large tax bill from the IRS, forcing him to sell many of his possessions. To pay off his debts, Cage acted in a lot of movies in a short period. More recently, he’s been praised for strong performances and his career is thriving again.

50 Cent

Curtis Jackson, also known as 50 Cent, created a successful business empire through his music and a profitable partnership with Vitamin Water. However, legal battles and a failed headphone venture caused financial difficulties. In 2015, he filed for Chapter 11 bankruptcy to restructure his debts, which at the time totaled millions. He ultimately resolved the bankruptcy by paying off over $20 million. Today, he continues to thrive as a producer of hit television shows like ‘Power’ and as a recording artist.

Kim Basinger

Kim Basinger almost lost all her money after buying the town of Braselton, Georgia, for $20 million. Her plan to turn it into a popular tourist spot didn’t succeed, and she couldn’t afford to pay a legal judgment from a lawsuit over the movie ‘Boxing Helena’. This led her to file for bankruptcy and sell the town for much less than she originally paid. Later, she successfully revived her career with an Oscar-winning performance in ‘L.A. Confidential’.

Burt Reynolds

Burt Reynolds was a huge movie star in the late 1970s. However, expensive habits and a difficult divorce from Loni Anderson seriously depleted his wealth. Poor business decisions, including investing in a failing restaurant chain, made things worse. In 1996, Reynolds declared bankruptcy, reporting $10 million in debts. He continued to act in movies and TV shows consistently throughout his life to support himself.

Willie Nelson

Country music legend Willie Nelson faced a serious financial crisis when the IRS claimed he owed $32 million in unpaid taxes. His accountants were accused of mishandling his money, and the government seized his assets in 1990. To help pay off the debt, Nelson released an album called ‘The IRS Tapes: Who’ll Buy My Memories?’ and spent years touring relentlessly. He eventually cleared his balance and regained financial stability, continuing his career as one of the most popular and enduring performers in music history.

Toni Braxton

Throughout her successful music career, Toni Braxton has faced financial difficulties and filed for bankruptcy twice. The first time, in 1998, was because of a bad record deal that didn’t pay her fairly, even though she’d sold millions of albums. She filed again in 2010 after health problems forced her to cancel a show in Las Vegas. Braxton managed to overcome these challenges by appearing on reality TV and releasing new music. Now, she actively promotes financial education for other artists.

Meat Loaf

Despite the huge success of his album ‘Bat Out of Hell’, Meat Loaf (Marvin Lee Aday) struggled with financial problems and legal issues early in his career. The pressure to create another hit caused him to lose his voice and stop earning income. He declared bankruptcy in the 1980s due to lawsuits from his songwriting partner. However, he made a remarkable comeback with ‘Bat Out of Hell II: Back into Hell’, which allowed him to restore his finances before his passing.

Larry King

Before becoming a famous talk show host, Larry King faced a serious financial crisis. In the early 1970s, he was accused of theft, which caused him to lose his radio job and fall into significant debt. By 1978, he filed for bankruptcy owing almost $400,000. He rebuilt his career by taking a late-night radio job in Washington D.C., which eventually led to national recognition. Later, his success on CNN made him a multi-millionaire.

Cyndi Lauper

Before becoming a superstar, Cyndi Lauper paid her dues performing with cover bands. Her first band, Blue Angel, didn’t become successful and actually led to a legal battle with their manager, pushing her into financial hardship. To stay afloat, she worked retail jobs and sang in restaurants while continuing to write songs. Everything changed when she released her debut solo album, ‘She’s So Unusual’. Today, Cyndi Lauper is a beloved icon, even winning a Tony Award for her work on the Broadway musical ‘Kinky Boots’.

Marvin Gaye

Marvin Gaye, known as the Prince of Soul, was very successful at Motown Records, but he faced personal and financial difficulties. His divorce from Anna Gordy was expensive, and he had to give her the royalties from his next album as part of the settlement. He also got into trouble with the IRS over unpaid taxes and briefly moved to Europe to escape his debts. Eventually, Gaye declared bankruptcy and even lived in a van at one point. He managed to revive his career with the hit song ‘Sexual Healing’ just before his untimely death.

Gary Coleman

Gary Coleman, famous for his role on ‘Diff’rent Strokes’, earned a huge salary as a child actor. Unfortunately, his parents and those managing his money improperly handled nearly all of his income through a problematic trust fund. While he did win a lawsuit against them, the costs of the legal battle ate up much of the money he recovered. This led to Coleman filing for bankruptcy in 1999, and he later worked as a security guard to make ends meet. He faced financial difficulties for the rest of his life.

Wesley Snipes

Wesley Snipes was a hugely popular action movie star in the 1990s, known for films like ‘Blade’ and ‘White Men Can’t Jump’. However, he faced serious legal issues when he was accused of not filing his taxes for multiple years. Snipes spent three years in prison and had to pay large fines, which cost him a lot of money. He’s gradually returned to acting, appearing in films like ‘Coming 2 America’, and is working hard to restore both his career and public image.

Stephen Baldwin

Stephen Baldwin, the youngest of the Baldwin brothers, lost his New York home to foreclosure after failing to keep up with his mortgage payments. He declared bankruptcy in 2009, reporting significant debts and back taxes. Finding steady acting roles proved challenging, making it hard for him to support his lifestyle. He later resolved his tax issues and shifted his focus to faith-based films and projects. Since then, he’s found more stability and has largely stepped away from the pressures of traditional Hollywood.

T-Pain

T-Pain was a huge star in the mid-2000s, and he lived a very lavish lifestyle. However, he later revealed he spent around forty million dollars on poor investments and things he didn’t really need. At one point, he was struggling so much he even had to borrow money for diapers. He turned things around by becoming an independent artist and winning the first season of ‘The Masked Singer.’ Now, T-Pain stays financially stable by streaming on Twitch and continuing to tour.

Dennis Rodman

Dennis Rodman made a lot of money playing in the NBA, but he had trouble managing it. Throughout his career, he faced many lawsuits and fines that used up his savings. Adding to his financial difficulties were unpaid child and spousal support payments. To earn money, Rodman appeared on reality TV shows like ‘Celebrity Apprentice’ and did promotional events.

Allen Iverson

Allen Iverson made over $200 million playing professional basketball. However, he struggled financially due to lavish spending on loved ones and problems with gambling. He faced legal issues, including a lawsuit from a jeweler and a court order to seize funds from his bank account. Fortunately, a long-term endorsement deal with Reebok, which includes a trust fund for his future, helped him out. Since then, Iverson has lived a more financially responsible life than he did during his basketball career.

Fantasia Barrino

Fantasia’s win on ‘American Idol’ initially promised a secure financial future. However, she quickly became responsible for supporting her entire family, which put a significant burden on her income. She faced losing her home in North Carolina and had to rebuild her life. Fantasia successfully turned things around by performing on Broadway and continuing to make music. Most recently, she’s been praised for her performance in the movie musical ‘The Color Purple’.

Sinbad

Comedian Sinbad experienced financial difficulties throughout his career, leading him to file for bankruptcy twice. In 2013, a second filing was triggered by a large tax debt owed to the IRS. He explained that high business costs and staff salaries contributed to his money problems. Despite these challenges, Sinbad continued to tour as a comedian to pay off his debts and remains a well-respected figure in comedy.

Wayne Newton

Known as ‘Mr. Las Vegas,’ the entertainer built a successful career performing on the Las Vegas Strip, but also dealt with many years of lawsuits over money. In 1992, he filed for bankruptcy protection to manage $20 million in debt. He also sued NBC, claiming a broadcast harmed his career and reputation, and he was eventually able to recover financially. Despite these challenges, his continued popularity allowed him to maintain his long-running show in Las Vegas.

Dionne Warwick

Okay, so Dionne Warwick – a true vocal legend, seriously one of the most successful female singers ever – had a really tough time with her finances. It turns out, later in her career, she discovered years of taxes hadn’t been paid properly. This led to her filing for bankruptcy in 2013, with debts exceeding ten million dollars. She maintains she wasn’t knowingly involved in any wrongdoing, but she took accountability for the money owed. Thankfully, she’s bounced back and, honestly, I’ve been loving her recent resurgence thanks to her hilarious and charming presence on social media. It’s great to see her thriving!

Isaac Hayes

Isaac Hayes, the iconic singer and voice of Chef from ‘South Park’, faced financial hardship after the record label Stax Records went bankrupt. He declared bankruptcy in 1976, deeply in debt with few possessions. As a result, he lost his house and even his Oscar for the film ‘Shaft’. Hayes worked hard to rebuild his life, finding success through voice acting and radio work, and was able to achieve stability again before his death in 2008.

Tom Petty

In 1979, Tom Petty used a bankruptcy filing as a legal strategy to get out of a bad contract with his record label. The label had been sold, and Petty didn’t want to be forced into a new agreement without his approval. This allowed him to cancel the old contract and negotiate better terms with a new label. Soon after, he released ‘Damn the Torpedoes,’ which became a huge hit. This daring decision protected his finances and gave him control over his music.

Mick Fleetwood

Fleetwood Mac’s drummer has faced financial difficulties throughout his life, filing for bankruptcy on seven separate occasions. His heavy drug use and wild lifestyle during the 70s and 80s quickly depleted the large sums of money he earned with the band. Bad decisions with property investments made things even worse. He’s continued to perform with Fleetwood Mac and work on individual projects to earn money. Even with these financial setbacks, he remains a highly respected and iconic figure in rock music.

Billy Joel

Billy Joel, known as the “Piano Man,” filed a lawsuit against his previous manager seeking $90 million in damages after uncovering significant financial fraud and poor management. The manager had improperly used Joel’s funds for speculative investments and personal loans. This led Joel to embark on extensive touring to recover the substantial financial losses. Through highly successful tours and album sales, he ultimately rebuilt his fortune, and his ongoing residency at Madison Square Garden has become one of the most profitable in entertainment history.

Sly Stone

Sly Stone was a groundbreaking funk musician who inspired many artists, but he unfortunately lost his wealth through drug use and unfavorable business deals. He disappeared from public view for years, and in 2011, was discovered living in a van in Los Angeles. Although he won a five million dollar lawsuit against his former managers, he faced difficulties actually receiving the money. He now lives a private life, away from the public spotlight.

George Clinton

George Clinton, the creative force behind Parliament-Funkadelic, lost ownership of his music because of complicated legal issues and unfair business dealings. He declared bankruptcy in 1984 and spent years trying to get his musical catalog back. To make a living and support his large band, he continued to tour constantly. After decades of legal fights, he finally regained some of the rights to his songs. He recently finished a final tour and has now retired from performing live.

Joey Lawrence

Joey Lawrence rose to fame as a teen idol on ‘Blossom,’ but later struggled with money problems. In 2017, he filed for bankruptcy because he was spending more than he earned. He’d built up a lot of credit card debt by living an expensive lifestyle. To pay off what he owed, he sold many of his possessions. Since then, Lawrence has made a comeback to TV, appearing in several sitcoms and reality shows.

Drake Bell

Drake Bell, known for his role on Nickelodeon, filed for bankruptcy in 2014, reporting around $600,000 in debt. After his popular show ended, his income decreased, and he struggled to keep up with his expenses. He lost his home to foreclosure because he owed more on the mortgage than the house was worth. Since then, Bell has focused on music and voice acting work to earn money, and continues to perform and tour to provide for his family.

Janice Dickinson

Janice Dickinson, considered the first supermodel, faced financial difficulties and filed for bankruptcy in 2013. Despite success on reality television, she had trouble managing her money and owed a significant amount in back taxes and cosmetic surgery bills. Over several years, she worked to repay her debts through public appearances. Now married to a wealthy doctor, her life is more stable, and she continues to be a well-known figure in fashion and entertainment.

Gary Busey

In 2012, actor Gary Busey filed for bankruptcy, reporting assets worth less than $50,000. He was in debt to the IRS, as well as several lawyers and medical facilities. His inconsistent work history, due to personal and health challenges, made it difficult to find steady, well-paying jobs. Busey was able to eliminate his debts through bankruptcy and continued working in TV and film. He’s since gained a devoted following for his unusual personality and often unpredictable interviews.

Teresa Giudice

Teresa Giudice, known from ‘The Real Housewives of New Jersey,’ and her husband, Joe Giudice, filed for bankruptcy in 2009. They were later accused of fraud for concealing money and being dishonest in court. Teresa spent almost a year in prison and was ordered to pay substantial fines. Since her release, she’s worked to rebuild her life and career, and continues to be a main cast member on the reality show. She’s also become a bestselling author.

Boris Becker

In 2017, tennis star Boris Becker faced financial ruin and was declared bankrupt in London due to an unpaid debt. He’d lost a significant amount of his wealth through his divorce and unsuccessful investments in Nigeria. Later, he was convicted of concealing assets while dealing with his bankruptcy and served time in prison. After his release, he was deported back to Germany, where he’s now working to rebuild his life and has returned to working as a sports commentator in an effort to repair his image.

Evander Holyfield

Evander Holyfield, despite earning over $200 million as a boxing champion, lost his 109-room mansion to foreclosure. Financial troubles, including child support payments and unsuccessful business ventures, led to mounting debts. The bank ultimately auctioned off his Georgia estate to settle what he owed. While Holyfield still makes public appearances and participates in exhibition matches, his story serves as a warning about how easily a large fortune can be lost.

Aaron Carter

Aaron Carter became famous as a young pop singer, but faced financial difficulties and filed for bankruptcy in 2013. He reported owing over $2 million, primarily in taxes. Carter said his parents had poorly handled his finances while he was growing up. He worked hard to revive his music career, often performing in concerts, before his untimely death. Now, his estate is being used to settle any outstanding debts.

David Cassidy

David Cassidy, best known from ‘The Partridge Family,’ struggled with financial difficulties and health problems, ultimately filing for bankruptcy in 2015. He had been diagnosed with dementia, forcing him to stop touring – his main source of income. To pay off debts, he sold his house in Florida. Cassidy passed away in 2017, leaving behind a complex financial situation, and his story illustrates how vulnerable many early television stars are when it comes to long-term financial stability.

Mickey Rooney

Mickey Rooney was a huge Hollywood star, but surprisingly, he didn’t have much money when he passed away. He faced financial difficulties, even declaring bankruptcy in 1962, and later claimed his stepson hadn’t handled his money well. Rooney spoke to Congress about the dangers of elder abuse and financial exploitation, sharing his own experiences. Despite working for over 90 years, he struggled to build lasting wealth and continued to work to support himself until the very end of his life.

Sammy Davis Jr.

Sammy Davis Jr., a famous singer and actor known for being part of the Rat Pack, lived a very lavish life. When he passed away in 1990, he owed the government millions in taxes. Initially, his estate didn’t have enough money to cover these debts. However, his widow dedicated years to paying them off and rebuilding the value of his name and image. Today, the estate is financially successful and handles all rights related to his work.

Judy Garland

Judy Garland’s incredible performance in ‘The Wizard of Oz’ made her a star, but she struggled with money problems for most of her life. She accumulated a large debt in back taxes and frequently depended on the generosity of friends for a place to live. It’s believed that those who managed her career exploited her, especially when she was at her weakest. She often had to perform even when she wasn’t well to cover her expenses. Sadly, despite being a legend, Garland died with very little money.

Debbie Reynolds

I was such a fan of Debbie Reynolds! It’s incredible how she overcame so much. After her husband lost almost all her money through gambling and bad investments, she was left with millions in debt. But she didn’t give up! She worked so hard, performing on Broadway and in Vegas, determined to pay everyone back – and she did! She even managed to rebuild her finances and create a place for all her amazing career keepsakes with a hotel in Las Vegas. To me, she’s a true inspiration – a testament to strength, hard work, and never giving up.

Francis Ford Coppola

Francis Ford Coppola, the director of ‘The Godfather’, faced financial ruin when his musical, ‘One from the Heart’, was a costly box office failure. He spent the next ten years directing mainstream films like ‘Jack’ and ‘The Rainmaker’ to cover the resulting debts. Coppola then revitalized his career and finances through his highly successful winery, which now allows him to independently fund his current creative projects.

Stan Lee

Stan Lee, the legendary co-creator of Marvel Comics, experienced significant hardship later in life. His first company, Stan Lee Media, failed during the dot-com bubble burst, and he lost his investment when partners were accused of illegally inflating the stock price. He then started a new venture, POW! Entertainment, but also dealt with troubling accusations of financial exploitation and elder abuse in his final years. Despite these difficulties, he remained a cherished public figure for Marvel fans until his passing.

Tell us which celebrity comeback story surprised you the most in the comments.

2026-02-05 15:57