Rough sleepers lay in their makeshift beds outside closed shops, at daybreak on Oxford Street in London on August 2, 2023. Homeless has soared across Britain where a cost of living crisis has left many struggling to make ends meet. The CPRE charity said o

Money management is not a skill everyone automatically masters when they reach adulthood, acquire wealth or gain fame. Lavish lifestyles, bad investments, global financial crisis and many other reasons could be cited as contributing factors to anyone going bankrupt or falling into homelessness.

The same can be said for these 28 celebrities who became homeless or broke:

1. Dennis Rodman

Dennis Rodman
Dennis Rodman played 23 games for the Los Angeles Lakers. Getty Images/Icon Sportswire

Dennis Rodman, Michael Jordan's previous teammate and famous rebounder when he was a successful basketball player, found himself barely able to afford living expenses in 2012, according to Fox Sports. His lawyers said he could not pay for child support for his two kids, reportedly owing over $800,000 in back child support.

2. Burt Reynolds

Burt Reynolds films
Burt Reynolds, pictured in 1975, had a film career spanning six decades. Hulton Archive/Getty Images

A famous movie star from the '60s to the '80s, Reynolds spent on real estate, 150 horses, a private jet and over $100,000 in toupees, according to Vanity Fair. He also had an expensive marriage followed by an expensive divorce with a dwindling income, making him unable to pay for his loan to CBS.

He filed for bankruptcy in the '90s with over $11 million in debt, reported Insider. He said he had "lost more money than is possible" because he was not watching it.

3. Marvin Gaye

Soul singer Marvin Gaye, one of the most famous musicians of all time and even referenced in other musicians' hits, filed for bankruptcy in 1976 due to missed alimony payments to his first wife. A judge ordered Gaye to pay $600,000 from royalties of his album "Here, My Dear" to ex-wife Anna Gordy Gaye.

According to Grunge, he had accumulated $9.2 million in debt when his life ended.

4. Stephen Baldwin

 Actor Stephen Baldwin is accused of repeated failure to file personal income tax returns for 2008, 2009 and 2010.  Rockland County District Attorney's Office

Actor Stephen Baldwin filed for bankruptcy in 2009 after owing over $2 million in debt from tax payments, credit cards and mortgages, reported ABC News. In 2012, Baldwin was arrested for not filing his state taxes for three consecutive years.

He pled guilty and avoided jail time by paying off $300,000 in tax liabilities, as per The Blast. Baldwin mentioned in a CNN interview that his accountants did not handle his taxes appropriately.

5. Aaron Carter

Aaron Carter
Aaron Carter attends 102.7 KIIS FM's 2017 Wango Tango at StubHub Center in Carson, California, May 13, 2017. Getty Images/ Frazer Harrison

The former child star is known for the hit "I'm All About You," Carter talked to Us Weekly in 2016 about not having savings. For Spike's show "Life or Debt," Carter admitted to a financial advisor that he was in a terrible position, financially. He said when he turned 18, he "got hit with all those taxes." Over $1 million in taxes, per Us Weekly.

He mentioned filing for bankruptcy in 2015 and already being over $100,000 in debt a year later.

6. Teresa and Joe Guidice

Joe Guidice, Teresa Guidice
Joe and Teresa Guidice are pictured leaving court on Aug. 14, 2013, in Newark, New Jersey. Getty Images/Mike Coppola

The couple of "Real Housewives of New Jersey" fame filed for bankruptcy in 2009, claiming they were $10 million in debt, according to People. The two were also allegedly hiding assets and were charged by creditors with bankruptcy fraud, on top of other charges.

After Joe's deportation, the couple decided to divorce amicably in 2019.

7. David Cassidy

David Cassidy
David Cassidy died on Nov. 21, 2017. The actor is pictured arriving at Disney-ABC Television Group Summer Press Tour Party on Aug. 8, 2009 in Pasadena, California. Frazer Harrison/Getty Images

Cassidy sold over 25 million records at the height of his career, People said. However, with $10 million in debt, the star of "The Partridge Family" filed for bankruptcy in 2015. He had a history of financial troubles, health issues and DUIs. Following his third DUI, Cassidy's wife filed for divorce. Cassidy had to put up his mansion for auction to finance his divorce.

He passed away in November 2017, but a voice recording revealed in 2018 that he had admitted to lying about his health conditions.

8. Ted Hawkins

From being a largely anonymous street performer, the Mississippi-born singer lived a "hobo-like existence," reported the Los Angeles Times, "hopping trains up and down the East Coast." He eventually moved to Los Angeles for its warmer weather.

Hawkins played on the Third Street Promenade and was discovered by a record producer, leading to his popularity in Australia and Europe performing in small concert halls and clubs. He died of a stroke in 1995, barely a year after the release of his first major label recording, "The Next Hundred Years." He was reportedly working on a new album at the time of his death, mentioned UPI.

9. Randy Quaid

Randy Quaid
Nomination: Best Supporting Actor in "The Last Detail” in 1973. Reuters

The actor appeared in more than 90 films throughout his career, including "Brokeback Mountain," but he faced some financial troubles as well. He and his wife were charged for not paying hotel bills over $10,000. He eventually ended up squatting in the guest house of a property they used to own. In 2010, Reuters reported the couple had been arrested for squatting.

10. John Blyth Barrymore

The son of John Drew Barrymore and half-brother of superstar Drew Barrymore, John Blyth Barrymore suffered countless comparisons to his father and the rest of the actors from the Barrymore clan.

He became famous for acting in horror films and comedies but became homeless in 2012. He had to rely on a government benefit card to get free food from the local grocery store.

11. Iran "The Blade" Barkley

The former boxer made around $5 million throughout his career in the '80s and '90s – all of which he lost. He then moved in with his niece living in a public housing development in the Bronx. His niece eventually evicted him, prompting the boxer to sleep in subway vehicles. He was seen sleeping in Howard Johnson Express in 2010, reported the New York Post.

12. Margot Kidder

'Superman' Actress Margot Kidder’s Death Ruled Suicide
Margot Kidder's death was ruled as a suicide by Coroner. In this image: Undated file photo shows US actress Margot Kidder, 47, who was found 24 April after missing for thee days. Getty Images/File AFP

Kidder was famously known for playing the role of Lois Lane in the "Superman" movies opposite Christopher Reeve. People mentioned Kidder's battle with mental health and her refusal to get treatment. She slept in cardboard boxes and backyards in Los Angeles in 1996. The outlet also learned she was missing her front teeth and her hair got hacked off. She died at the age of 69.

13. Brett Butler

Butler became popular because of the ABC sitcom "Grace Under Fire." However, it was also during the show's run that she started her recurring battle with drug addiction, according to The Hollywood Reporter in a 2011 article. The show was canceled in 1998, so Butler moved from L.A. to a farm in Georgia to live with 15 pets. After all her money ran out, she moved to a homeless shelter.

In 2021, a GoFundMe page for Brett was set up amid her imminent eviction from her apartment. She has since been attempting to make a career comeback by developing a reality show and performing at the Downtown Comedy Club in LA.

14. Rocky Lockridge

A world boxing champion of the '70s and '80s, Lockridge's winning stride faltered, so he started to lose everything. Talking to Todd Schmerler of The Star-Ledger, Lockridge admitted he had a drug addiction spanning over two decades, noting he would party for "two weekends" after each fight.

Schmerler mentioned Lockridge "has no money," and his body "tilts to one side when he walks" as a result of a stroke in his report. He had been living on the streets of New Jersey for ten years before succumbing to complications from a stroke at age 60, reported TMZ Sports.

15. Ray "Sugar" Williams

Williams was once famous as a basketball player for the New York Knicks and the Boston Celtics. He declared bankruptcy in 1994, after his retirement. The Boston Globe reported he became homeless, living in the back seat of his 1992 Buick in 2010.

Williams said in an interview that the NBA should take better care of their retired players.

"When I played the game, they always talked about loyalty to the team," he said. "Well, where's the loyalty and compassion for ex-players who are hurting? We opened the door for these guys whose salaries are through the roof."

Former teammates Kevin McHale and Larry Bird provided financial assistance to Williams to help him get back on his feet. Unfortunately, he eventually succumbed to cancer at age 58.

16. Houston McTear

The two-time Olympic qualifier and once-known as "the world's fastest human," McTear moved from Florida to Los Angeles and tried boxing under Muhammad Ali and Harold Smith, who was assigned to run his track club, shared AOL. When the club went under, McTear lost his support, and he ended up sleeping on Santa Monica Beach for three years.

He was rescued by an older woman and eventually started a family. In 2015, McTear died of lung cancer.

17. Debbie "Storm" Clark

"American Gladiators" star Debbie Clark, popularly known as "Storm," performed as one of the Gladiators on the show for three years. After a career-ending injury, she went on to work as a personal trainer, chef and country singer, with little success. Clark ended up on the streets of San Diego, homeless with her son.

In 2011, Patch published the story of Embrace CEO Sean Sheppard allowing Storm and her son Crayton to stay with him, setting up rules for the arrangement.

18. Floyd Mayweather Jr

 Floyd Mayweather
Floyd Mayweather Getty Images | Katelyn Mulcahy

Retired boxer Floyd Mayweather, Jr. owed the IRS $22.2 million in debt from 2015, ESPN reported in 2017, citing a notice of federal tax lien from the government. The same year, Mayweather filed a court petition for a reprieve from his unpaid taxes until after his fight with UFC star Conor McGregor. The court argued that he had enough resources for his debt payment, even if it required taking out a loan or selling some of his assets.

Currently, he is active in matches based around entertainment and generating interest, reported SportsNaut.

19. Nicolas Cage

Nicolas Cage
Nicholas Cage, who is notoriously behind on his payments to the tax man, has settled $6.25 million in back taxes. Reuters

Actor Nicolas Cage is known for his extensive body of work in Hollywood, including "National Treasure" and "Ghost Rider." He reportedly had earnings of $40 million just in 2009. Cage spent his money on 15 homes, automobiles, a burial tomb, shrunken pygmy heads and other rare artifacts, reported CNBC.

In 2012, TMZ learned that the IRS had placed liens on Cage and demanded over $6 million for his 2007 taxes. The tabloid also said he "fell around $13 million behind in taxes for 2002, 2003, 2004 and 2007." According to Cage, his former business manager led him to this financial ruin.

Cage had to sell personal items on his way back to solvency. From a net worth of over $100 million, his net worth is now at $25 million this 20122, according to Celebrity Net Worth.

20. Mike Tyson

Former Heavyweight champion Mike Tyson will not face criminal charges over a fight on a plane last month
Former Heavyweight champion Mike Tyson will not face criminal charges over a fight on a plane last month GETTY IMAGES NORTH AMERICA via AFP / AL BELLO

Retired boxer Mike Tyson, once a heavyweight champion who earned about $30 million per fight, reportedly owed money to the IRS, British tax authorities and many others, on top of paying $9 million in a divorce settlement. He was also behind on child support, reported The New York Times in 2003. In total, his debt amounted to over $27 million. Tyson filed for Chapter 11 bankruptcy and stated he had been in financial distress since 1998 due to a "substantial debt to Showtime, taxing authorities and parties to litigation."

Tyson has been slowly trying to regain his fortune by acting, launching a podcast and investing, said Insider.

21. 50 Cent

50 Cent
50 Cent won a lawsuit against a “Love & Hip Hop: Hollywood” cast member. The rapper is pictured attending the premiere of “Nobody’s Fool” on Oct. 28, 2018 in New York City. Angela Weiss/AFP/Getty Images

One of the popular rappers of the late '90s, 50 Cent reportedly had $32.5 million in debt in 2015. He eventually filed for bankruptcy. In 2016, CNN reported the rapper was ordered to appear in court after posting pictures of himself surrounded by cash.

"There's a purpose of having a bankruptcy process be transparent, and part of that purpose is to inspire confidence in the process," the judge said at the Connecticut hearing. "When that process becomes very public, the need for transparency, I believe, is even higher."

50 Cent bounced back from his financial struggles and started rebuilding his wealth. He now has a net worth of $40 million, according to

22. Kim Basinger

Kim Basinger 8 mile now
Actress Kim Basinger attends the premiere of ‘Fifty Shades Darker’ at The Theatre at Ace Hotel on Feb. 2, 2017 in Los Angeles. Alberto E. Rodriguez/Getty Images

Kim Basinger, of "Batman" and "8 Mile" fame, declared bankruptcy in 1993, reported Chicago Tribute. Basinger was sued by Carl Mazzocone for breach of contract to star in the film "Boxing Helena." She had a net worth of $5 million at the time. Basinger had to pay damages and lawyer fees, eventually settling with Main Line Pictures.

Basinger recovered from bankruptcy after starring in "LA Confidential," which earned her an Academy Award, reported CNBC. She currently has a net worth of $20 million this 2022.

23. Larry King

Larry King was best known for a 25-year run as a talk show host on CNN
Larry King was best known for a 25-year run as a talk show host on CNN GETTY IMAGES NORTH AMERICA / Rich Fury

A famous TV host and personality, Larry King's broadcast career started in the '50s as a radio announcer in Florida. In 1971, he was charged with grand larceny, reported Time. Even though the charges got dropped, he fell into debt. He filed for bankruptcy in 1978 after being unable to hold a regular journalism job for more than four years, which added to his debt.

He recovered when he got offered to host a national radio talk show, which spawned the successful "Larry King Live" on CNN from 1985 to 2010.

24. Cyndi Lauper

Cyndi Lauper
Cyndi Lauper slammed Madonna for her profanity-laced speech at the Women's March on Jan. 21. Pictured: Lauper performs before the 85th annual Hollywood Christmas Parade in Los Angeles on Nov. 27, 2016. Reuters/Phil McCarten

Before Lauper's career as a solo artist, she was part of the group Blue Angel, whose first and only album was a flop. When they fired their group manager Steve Massarsky, he responded by suing the group for $80,000, shared Grunge, which resulted in Lauper filing for bankruptcy in 1981.

Lauper recovered from bankruptcy and gained success in her solo career. She even won best new artist in 1985 at the Grammys. Today, Lauper's net worth is $50 million.

25. Toni Braxton

Toni Braxton
Toni Braxton is being accused of fraudulently transferring money to her husband in her bankruptcy case. REUTERS

Talking to ABC in a 2012 interview, Braxton got candid about having to file for bankruptcy in 1998 because her recording contract was paying her poorly. According to the artist, she received less than $2,000 in royalties. Braxton also talked about indulging in "girly things," including plates and Fabergé eggs.

She recovered from bankruptcy in the 2000s. But she had to cancel the remaining shows in her two-year Las Vegas residency due to health reasons, prompting another bankruptcy filing in 2008.

Braxton was able to recover from her second bankruptcy. On her reality TV show "Braxton Family Values," she mentioned that the bankruptcy had "worked out really great" for her. The federal court discharged most of her debt and allowed her to keep her possessions. She also said she had to monitor everything because she was on a budget.

In 2022, her estimated net worth is $8 million.

26. T-Pain

T-Pain is no stranger to financial ups and downs. At the height of his music career, he said he had $40 million in the bank. But in an interview with "The Breakfast Club," he said he had to borrow money to buy Burger King for his kids.

Citing bad investments and spending habits, he said the experience made him re-think how he managed his finances. T-Pain is currently financially stable and has learned the value of sound financial management skills. His net worth in 2022 is estimated to be $10 million.

27. Natasha Lyonne

Natasha Lyonne
Natasha Lyonne speaks at the Build LDN event at AOL London on June 1, 2017, in London, England. Getty Images/Tim P. Whitby

The star of "American Pie" and "Slums of Beverly Hills" in the '90s had her career "derailed" after run-ins with the law. According to Inside Movies, Lyonne was arrested for DUI in 2001 and charged with "mischief, trespass, and harassment of a neighbor (and the neighbor's dog) in 2004."

She was hospitalized for "a variety of ailments" in 2005. She eventually got evicted from a friend's townhouse and ended up on the streets, according to the New York Post.

Lyonne has since revived her acting career by appearing on shows such as "Orange is the New Black" and "Law and Order: SVU."

28. Danny Bonaduce


Another actor from the hit "The Partridge Family" fell into homelessness after stints in rehab. Talking to Oprah, Bonaduce recalled his unusual life of homelessness while being famous: "I was still famous and people had no idea I lived behind the dumpster... I'd be taking pictures with people and signing autographs."

He recovered and has been co-hosting "The Danny Bonaduce & Sarah Morning Show" on Seattle radio station KZOK since 2011, according to Page Six.

29. Ulysses S. Grant

Ulysses S. Grant

Ulysses S. Grant, renowned Civil War general and 18th President of the United States, faced financial ruin after his presidency due to failed business ventures. Despite his success in military and political realms, Grant's investments led to bankruptcy. Joining his son's brokerage firm, Grant & Ward, he unknowingly became entangled in a Ponzi scheme orchestrated by Ferdinand Ward. Grant's financial struggles intensified, leading him to write memoirs in a race against time to provide for his family. Just days after completing his memoirs, Grant passed away on July 18, 1885.

30. Evander Holyfield

Mike Tyson Evander Holyfield Holy Ears
Mike Tyson and Evander Holyfield have partnered together on cannabis-infused gummies called "Holy Ears" Tyson 2.0

Evander Holyfield, a former American professional boxer active from 1984 to 2011, achieved remarkable feats including an Olympic bronze medal and becoming the World Heavyweight Champion four times. Despite earning an estimated $230 million in prize money, his extravagant spending, coupled with IRS troubles, foreclosures, and hefty mortgages, led to the loss of his Georgia mansion, Olympic medal, and other possessions. Consequently, his net worth dwindled to a mere $500,000.

In June 2008, Washington Mutual Bank announced the foreclosure auction of Evander Holyfield's $10 million suburban Atlanta estate. Holyfield faced lawsuits for unpaid child support and debts totaling $550,000, alongside financial troubles from lavish spending, failed ventures, and three divorces. Despite earning £350 million (US$513 million) in his boxing career, he was labeled "flat broke and bankrupt" by The Independent in 2012. By 2019, his income primarily stemmed from personal appearances, totaling around $1.2 million annually.

31. Lindsay Lohan

Lindsay Lohan in Mean Girls
Mean Girls/Paramount Pictures

Lindsay Lohan, known for roles in "The Parent Trap," "Mean Girls," and "Herbie: Fully Loaded," is an American actress and singer born in New York City and raised on Long Island. Beginning her career at age three with Ford Models, her success waned due to reputation for being difficult to work with, attributed to her partying lifestyle.

Financial troubles ensued, compounded by taxes and legal fees. Charlie Sheen reportedly assisted her with bills during her tough times. Initially worth $28 million, her net worth has diminished to $800,000 to $1 million. In 2019, she starred in the MTV reality series "Lindsay Lohan's Beach Club," set in her Greek resort. Currently, she lives in Dubai.

32. Pamela Anderson

Pamela Anderson in France
Pictured: US actress Pamela Anderson poses during a photocall upon arriving to attend the "Diner de la Mode" (Fashion Dinner) fundraiser dinner to benefit French anti-AIDS association Sidaction, on January 24, 2019, at the Pavillon d'Armenonville in Paris. THOMAS SAMSON/AFP via Getty Images

Pamela Denise Anderson, a Canadian-American actress, model, and media personality, rose to fame as the February 1990 Playboy Playmate of the Month and for her role in the iconic series "Baywatch", solidifying her as a sex symbol. Facing financial challenges during mansion renovations in 2009, Anderson struggled with substantial tax debts, as reported by People magazine. Her short-lived marriage to producer Jon Peters in 2020 ended amidst allegations of control, disputed by Peters in an interview with Page Six. Anderson's real estate ventures include purchasing a Malibu beach home in 2001, later renting it for $50,000 per month. She briefly lived in Cassis, France, before moving to Vancouver Island in Canada in 2019, making her residency permanent in 2021, and subsequently selling her Malibu property.

33. Wesley Snipes

Wesley Snipes
Wesley Snipes attend the German premiere of the film "The Expendables 3" in Cologne, Germany on August 6, 2014 Wikimedia Commons

Wesley Snipes, known for his roles in Hollywood, faced significant tax issues, serving over two years in prison for tax fraud and owing the IRS more than $23 million due to late tax payments, resulting in foreclosure on multiple homes. Snipes spent three years in prison for tax evasion in 2008, fined $5 million for failure to file past tax returns, as reported by People. Since his release from prison, he has resumed his acting career, appearing in numerous films and TV shows, including the recent "Coming 2 America" alongside Eddie Murphy.

34. Fantasia Barrino

Fantasia Barrino performing in Cincinnati, February 2017
Fantasia Barrino performing in Cincinnati, February 2017 Wikimedia Commons

Winner of Season three of "American Idol," Fantasia Barrino soared to fame with hit singles, Grammy nominations, and a Broadway role in "The Color Purple." However, shouldering the financial responsibility for her family took its toll. Entrusting her finances to others resulted in her home being auctioned and missed performances, leading to substantial refunds. Reflecting on her experiences, Fantasia emphasized the importance of financial management in a 2010 Oprah article. Despite setbacks, she shared in a 2019 interview her journey of rebuilding, expressing resilience by embracing her roots and self-sufficiency through cooking. In a 2019 interview for the Tammi Mac show, Fantasia revealed that she's been slowly building herself back up. "I lost everything twice. So, I cook my own food. I don't need no chef. I'm from North Carolina; my grandma and my mama taught me how to cook," she said.

35. Sly Stone

Sly Stone
Sly Stone play the Opera House in Bournemouth Wikimedia Commons

Sylvester Stewart, also known as Sly Stone, is an iconic American musician, songwriter, and record producer renowned for his leadership role in Sly and the Family Stone, a band pivotal in shaping the soul and funk music scene of the 1960s and 1970s. Despite once experiencing fame and wealth, Stone's life took a downturn, leading to financial struggles and homelessness. Documentaries have shed light on his dire financial situation, attributing it to disputes over royalty payments and misfortune. On August 18, 2009, The Guardian reported that the forthcoming documentary, "Coming Back for More" by Dutch director Willem Alkema, claims Stone is homeless and living off welfare. On September 25, 2011, Alkema wrote in the New York Post that Stone was homeless and living out of a white camper-van in Los Angeles: "The van is parked on a residential street in Crenshaw, the rough Los Angeles neighborhood where "Boyz n the Hood" was set. A retired couple makes sure he eats once a day, and Stone showers at their house."

36. Hugh Hefner

Hugh Hefner
Hugh Hefner in trademark pajamas with girlfriend Carrie Leigh in front of Playboy Mansion Wikimedia Commons

Hugh Hefner, the iconic founder and editor-in-chief of "Playboy" magazine, expanded the brand globally with Playboy Clubs and indulged in luxurious mansions where he hosted wild parties with Playboy Playmates. Despite his penchant for lavish spending, his publications' earnings reached as high as $45 million. Towards the end of his life, Hefner received a $1 million salary and was granted a nominal $100 per year rent to reside in the Playboy Mansion, having sold the property as part of the sale of all Playboy enterprises to a private equity firm. Even as the firm paid $217 million to shareholders, Hefner's compensation was limited to his salary and mansion privileges. Estimates of his net worth, drawn from 2009 divorce papers detailing $43 million in assets excluding Playboy stock, are contrasted by his hefty monthly expenses of $120 thousand, totaling roughly $7.4 million from the sale of his company to his passing, exceeding the $5 million earned in salary after taxes during the same period. At 91 years old, when Hugh Hefner passed away in the Playboy mansion, his surprisingly modest net worth consisted primarily of the mansion itself. Despite speculations about his wealth, a thorough review of his financial records revealed relatively little assets at his death.

37. Kellis

Kelis performing at Palmesus 2011, Norway
Kelis performing at Palmesus 2011, Norway. Wikimedia Commons

Kelis Rogers, known as Kelis, is an American singer-songwriter and chef. The singer, known for her breakout hit "Milkshake" in the 90s, faced financial challenges following her divorce from hip-hop artist Nas in 2009, as reported by TMZ. Pregnant at the time, Kelis sought increased child support from Nas in 2018, citing her $25,000 monthly expenses, according to Page Six. Despite financial strains, she generated income from her entertainment and touring company, as well as her food business. In a 2020 profile, it was disclosed that Kelis currently lives on a 10-acre farm located two and a half hours away from Los Angeles.

38. Mickey Rooney

Mickey Rooney
Wikimedia Commons

Mickey Rooney, born Joseph Yule Jr., was an American actor, producer, radio entertainer, and vaudevillian, recognized for his prolific career spanning nearly nine decades and over 300 films. Renowned as one of the last surviving stars of the silent-film era, Rooney's versatility shone as he transitioned from leading roles to celebrated character actor. Despite his immense success, including being the top box-office attraction and one of the highest-paid actors of his time, Rooney battled persistent financial woes, exacerbated by a gambling habit that led to bankruptcy multiple times. Despite ongoing struggles, Rooney continued performing until his passing in 2014, with his personal assets valued at a modest $18,000.

39. David Siegel

David Siegel
Wikimedia Commons

David Alan Siegel, an American entrepreneur, is the founder, president, and CEO of Westgate Resorts Ltd, a prominent Florida-based timeshare resort firm. His diverse business portfolio includes ventures in real estate, construction, hotel and apartment management, travel services, insurance, transportation, and retail. Siegel gained widespread attention when he, along with his wife Jackie, embarked on the ambitious project of building Versailles, an 85,000-square-foot residential construction in Florida modeled after the French palace of Versailles, as depicted in the 2012 documentary film "The Queen of Versailles." However, the project faced setbacks during the 2008 financial crisis, prompting Siegel to redirect his resources towards stabilizing his company amidst economic challenges. Despite adversity, Siegel's resilience has seen him on the path to reclaiming billionaire status, overcoming obstacles that once seemed insurmountable.

40. Courtney Love

Courtney Love performing in Detroit, 2013
Courtney Love performing in Detroit, 2013 Wikimedia Commons

Courtney Michelle Love, an American singer, guitarist, songwriter, and actress, emerged as a prominent figure in the alternative and grunge scenes of the 1990s. With a career spanning four decades, Love gained recognition as the lead vocalist and rhythm guitarist of the alternative rock band Hole, which she founded in 1989. Known for her provocative live performances and confrontational lyrics, Love's personal life, particularly her marriage to Nirvana guitarist Kurt Cobain until his death in 1994, has drawn significant public attention. Despite her influence in alternative culture, Love has faced financial challenges, including excessive spending, addiction, and legal disputes, leading to the loss of her late husband's assets and royalties. She has been involved in litigation with other Nirvana members, further impacting her financial stability.

41. Frances Farmer

Frances Farmer
Wikimedia Commons

Frances Farmer, a prominent figure in mid-century American cinema, rose to fame in the 1930s and '40s, starring in 15 films alongside luminaries like Bing Crosby and Cary Grant. Despite her success, her tumultuous personal life and mental health struggles overshadowed her career. After a period of decline in the 1940s, Farmer made a brief return to television in the late 1950s with the support of her husband, Leland Mikesell. She later battled esophageal cancer and passed away in 1970 at the age of 57.

42. Veronica Lake

Veronica Lake
Wikimedia Commons

Veronica Lake, the American film actress and pin-up model born Constance Frances Marie Ockelman, gained fame for her roles in "Sullivan's Travels" and as a femme fatale in film noir alongside Alan Ladd during the 1940s. Her life was marred by broken marriages, mental illness, and alcoholism, leading to financial struggles and eventual descent into obscurity. After facing evictions, violence, and menial jobs, including work in a lingerie factory, she was discovered working as a barmaid in New York City under the name Connie De Toth. She later moved to Miami and England, continuing her acting career in plays and low-budget films. Lake passed away in Burlington in 1973, due to acute hepatitis.

43. Robert "Bobby" Cletus Driscoll

Robert "Bobby" Driscoll
Wikimedia Commons

Driscoll was an American actor celebrated for his roles in iconic Walt Disney Studios films like "Song of the South" (1946), "So Dear to My Heart" (1949), and "Treasure Island" (1950). He also lent his voice to "Peter Pan" (1953) and received an Academy Juvenile Award for outstanding performances in "So Dear to My Heart" and "The Window". However, his career waned in the mid-1950s, leading to guest appearances on TV series, and he struggled with drug addiction, ultimately facing prison time. Following his release, he immersed himself in the avant-garde art scene, but his health declined due to substance abuse. In 1968, he was found dead in an abandoned building in Manhattan.

44. Gary Busey

Gary Busey at the Billboard-Children Uniting Nations after-party red carpet
Gary Busey at the Billboard-Children Uniting Nations after-party red carpet, 2008 Wikimedia Commons

Gary Busey is an American actor known for his dynamic performances in film and television. With a career spanning several decades, Busey has portrayed a wide range of characters, from intense and eccentric to comedic and dramatic. He gained prominence for his roles in films such as "The Buddy Holly Story," for which he received an Academy Award nomination, and "Lethal Weapon." Busey's unique on-screen presence and memorable performances have solidified his status as a respected and versatile actor in Hollywood. In 1988, Busey was involved in a serious motorcycle accident, resulting in injuries believed to have caused significant brain damage. By 2012, his net worth had plummeted to less than $50,000, with debts exceeding $500,000, leading him to file for bankruptcy. Despite his challenges, Busey's resilience shone through as he won the 14th season of Celebrity Big Brother in 2014. Additionally, in 2020, he starred in "Pet Judge," an Amazon Prime series, where he presides over a fictional court handling disputes over pets.

45. Willie Aames

Willie Aames
Wikimedia Commons

Willie Aames is an American actor, film and television director, television producer, and screenwriter, recognized for his roles as Tommy Bradford in the television series "Eight Is Enough," and the title character in the direct-to-video series "Bibleman." Beginning his acting career as a child in the late 1960s, Aames later struggled with alcohol addiction. In a 2017 interview with Studio 10, he recounted how his life took a downward spiral due to his battle with alcoholism, leading him from dining at the White House to homelessness. However, he managed to turn his life around by working as a satellite installer and later on a cruise ship. In 2015, Aames returned to acting in a Hallmark movie called "Harvest Stone" and continued to work on two more Hallmark films. Presently, he is married to his third wife and owns properties in L.A. and Vancouver while remaining active in the film and television industry.

46. Drake Bells

Drake Bells
Drake Bells Wikimedia Commons

Drake Bell, an American actor and musician, embarked on his entertainment career in the early 1990s, making his debut on shows like "Home Improvement" and "Seinfeld," before landing a prominent role on "The Amanda Show" alongside Amanda Bynes. His breakout came with the Nickelodeon series "Drake & Josh," where he starred as one of the titular stepbrothers. Alongside his acting, Bell pursued a music career, initially with the band Drake 24/7 and later co-writing and performing the theme song for "Drake & Josh." However, recent years have seen him entangled in legal troubles, including abuse allegations and criminal charges involving a minor. In 2014, he filed for bankruptcy, citing debts totaling $1.597 million against assets including his home valued at $1.575 million. Despite his early successes, Bell's recent controversies have overshadowed his once-promising career.

47. Corey Ian Haim

Corey Ian Haim
Corey Ian Haim Wikimedia Commons

The Canadian actor rose to fame during the 1980s as a teen idol, particularly known for his role alongside Corey Feldman in "The Lost Boys." The duo, often referred to as The Two Coreys, became iconic figures of the era, starring in several movies together and even featuring in a reality show. However, Haim's early success was marred by struggles with drug addiction, which persisted throughout his life. By the mid-2000s, his career had dwindled, leading to financial difficulties and even bankruptcy. In 2001, Haim found himself hospitalized due to drug-related issues. With no funds to cover his medical expenses, he resorted to a desperate measure, attempting to sell his teeth and hair on eBay. However, eBay intervened, as the sale of human body parts is prohibited on the platform. Despite attempts at a comeback, Haim tragically passed away in 2010 at the age of 38, unable to overcome his addiction woes.

48. Sonja Morgan

Real Housewives of New York City
Pictured [L-R]: Sonja Morgan, Leah McSweeney, Ramona Singer, Eboni K. Williams, and Luann de Lesseps are cast member on “The Real Housewives of New York City” Season 13. Sophy Holland/Bravo

An American television personality and entrepreneur, she gained fame through her starring role in the reality television series "The Real Housewives of New York City." Despite the show's glamorous facade, some cast members, like Sonja Morgan, have faced significant financial struggles. Morgan's past marriage to John Adams Morgan, a member of the influential Morgan family, ended in 2006, leaving her in financial turmoil. In the aftermath, she sold properties and paid off creditors over several years, including settling a $6.95 million debt from an abandoned movie project and relinquishing her home in Colorado, among other financial arrangements. Morgan filed for bankruptcy in 2010, citing debts exceeding $20 million. Subsequent legal issues, including a lawsuit for unpaid debts totaling $300,000 in 2016, added to her financial woes. However, Morgan's financial situation appears to have improved, largely due to her substantial earnings from the show, estimated at around half a million dollars per season.

49. Meat Loaf

US singer Meat Loaf, pictured here in 2006 in Hong Kong, has died aged 74
US singer Meat Loaf, pictured here in 2006 in Hong Kong AFP / Ted ALJIBE

Michael Lee Aday, professionally known as Meat Loaf, was a renowned American singer and actor celebrated for his commanding voice and theatrical performances. With a career spanning six decades, he emerged as one of the best-selling music artists in history, having sold over 100 million albums worldwide and starred in more than 65 films. His seminal album 'Bat Out of Hell,' released in 1977, remains one of the top five best-selling albums of all time, selling over 43 million copies and achieving platinum status 14 times over. Despite initial success in his music career, various challenges led Meat Loaf into a destructive drug addiction, exacerbated by financial troubles when his second album faltered. Battling poor money management and facing 45 lawsuits amounting to US$80 million, including disputes with songwriter Jim Steinman, Meat Loaf filed for bankruptcy. While the 1983 bankruptcy relieved Meat Loaf of overwhelming debt, it came at a significant cost, including the loss of his home and publishing rights to his songs. Nonetheless, Meat Loaf's financial situation improved over time, with his estate reportedly valued at $40 million upon his passing.

50. Curtis Montague Schilling

Curtis Montague Schilling
Curtis Montague Schilling Wikimedia Commons

Curtis Montague Schilling is a former American Major League Baseball pitcher and BlazeTV commentator. Renowned for his success on the field, including championship wins with the Arizona Diamondbacks and the Boston Red Sox, Schilling also ventured into the business world with 38 Studios, aiming to create a gaming sensation akin to World of Warcraft. Despite the initial excitement, 38 Studios faced financial troubles, culminating in bankruptcy and a breach of a taxpayer-funded loan agreement. Schilling, personally invested in the venture, lost millions and had to auction off prized memorabilia. However, he found stability as a color commentator and analyst at ESPN. Unfortunately, his tenure ended after he was fired for offensive social media posts.