14. 50 CENT
50 Cent, who’s real name is Curtis James Jackson III, Who used to be worth over $400Million filed bankruptcy last June days after a New York jury awarded fellow rapper Rick Ross’ baby mama, Lastonia Leviston, $7 million in a legal battle over her leaked sex tape. Which he has yet to fork over.
The lawsuit stemmed from a 13-minute video that appeared online in 2009 featuring a wig-wearing Fifty as a narrator dubbed Pimpin’ Curly.
The character made explicit remarks about Leviston and taunted rap rival Rick Ross, who at the time was trading barbs with Fifty via video, lyrics, and interviews.
50 Cent got the 2008 tape from the man in it – Leviston’s boyfriend at the time.
The 40-year-old rapper also lost a legal battle with his ex-business partners over a failed headphone deal and was slapped with a $17 million judgment in that case.
According to his Chapter 11 petition, Fifty claimed he had assets between $10 to $50 million but that his liabilities were in the same range.
A few months back, he filed documents in the bankruptcy stating he only had $16 million in assets.
Almost immediately after he became a star, DMX was making headlines for bad behavior. There were drug and weapons possession arrests, and charges of animal cruelty. He’d been ordered to make public service announcements and he’d gone to rehab, but DMX’s demons never seemed to subside.
One of the most notoriously bizarre moments happened in 2004, when DMX and an accomplice broke into the parking lot of New York’s John F. Kennedy International Airport after X told an attendant he was a federal agent, then attempted to commandeer a man’s SUV, with X telling the shocked driver he was working for the FBI. According to court documents, DMX then physically removed the driver from his vehicle—while the man’s 12-year-old daughter was in the car. Upon his arrest, police found a handgun, nightstick, 20 rocks of crack cocaine, Oxycodone, and Diazepam, and the rapper was charged with criminal possession of a weapon, criminal possession of a controlled substance, criminal mischief, driving under the influence, menacing, impersonation, and endangering the welfare of a child. He struck a plea deal where he only ended up serving under six weeks behind bars for violating parole.
He became a celebrity pariah more renowned for his bad behavior than catchy hits: the drug addiction, the seemingly endless litany of arrests, and his crumbling marriage to now-ex-wife Tashera Simmons (she separated from X in 2010 after he was incarcerated three times that year). X has also fathered 15 children with several women, he declared bankruptcy due to outstanding child support payments, and in July 2015 was sentenced to six months in jail for owing over $400,000 in back child support
12. TONI BRAXTON
Toni Braxton has sold more than 40 million albums in her career so far. But she’s filed for bankruptcy twice – in 1998, due to an abominably one-sided new artist contract with LaFace Records; and in 2010, after abruptly canceling a one-woman Las Vegas show because of her unexpected battle with lupus, leaving her with up to $50 million in debt.
Braxton has since launched a comeback with a hit reality TV series, The Braxton Family Values, a Lifetime movie, a Broadway stint, and a new collaboration album.
Braxton recently made the news when she purchased a $3 million home in the exclusive gated community in Calabasas, California, just six months after settling her second bankruptcy.
11. TERRELL OWENS, NFL LEGEND
Owens earned an estimated $70 million throughout his football career as a wide receiver. By 2012, he had blown through most of his fortune. Financial setbacks forced Owens to sell several of his high-priced homes for under market value; he was inundated with child-support payments upwards of $50,000 a month to four different women, and he was recently hit with a tax lien of nearly $500,000.
Owens has succeeded in reducing his child support payments. According to TMZ, last April he sued his financial advisers for “opening a bank account without his knowledge and then forging his signature, and leading him to really bad investments, including a failed Alabama casino.”
The talented football player has tried his luck at a comeback, but no NFL team has been willing to take a gamble on him.
10. T-BOZ OF TLC
The TLC singer filed for bankruptcy in 1995 and in 2011. Then last year, a judge dismissed her third bankruptcy case because T-Boz reportedly made no effort to settle her affairs, pay off her debts or appear at a creditors’ meeting. Hopefully her recent TLC network show, Totally T-Boz, generated some cash!
The first time Tionne “T-Boz” Watkins filed for bankruptcy was in 1995, after a famously short-shifting record deal from LaFace Records. The second time was in 2011. Watkins doesn’t have a history of living a lavish lifestyle, at least according to her public profile, however, she hadn’t been working much to supplement her reported $1200 a month in royalties.
In addition, Watkins had been burdened by medical bills after suffering from a brain tumor and sickle cell anemia. Her ex-boyfriend and child’s father Mack 10 has not settled on the reported $250,000 due in delinquent child-support payments.
The multi-platinum artist had a much better year in 2013 when VH1 premiered the biopic “CrazySexyCool: The TLC Story.” Watkins also joined her bandmate Chilli to release new songs.
9. EVANDER HOLYFIELD, HEAVYWEIGHT BOXER
Holyfield earned over $200 million dollars during a career that spanned more than two decades. The boxer had been teetering on the brink of financial ruin for some time when his 109-room mansion in Atlanta went into foreclosure in 2008. He would hold off the foreclosure for a few years but was forced to put the home on the auction block in 2012 to pay off $14 million he owed to financial firm JP Morgan Chase.
The home sold for $7.5 million. Holyfield owed $200,000 in back taxes and over $500,000 in child support payments as of 2012.
8. CHRIS TUCKER, ACTOR
Chris Tucker had become what few actors could brag about – the face of a successful franchise film. In 2007, Tucker negotiated a $25-million film deal to appear in Rush Hour 3, which made him the highest paid actor in Hollywood at the time.
Three years later, TMZ uncovered court documents that revealed Tucker owed $11 million in back taxes from 2001, 2002, 2004-2006, 2007. Tucker was forced to sell two Florida mansions and another in L.A. to pay down his debts. Last year he reportedly paid nearly $1 million toward the debt.
The “Friday” actor has been working steadily, including in a critically acclaimed role in the 2012 film “Silver Linings Playbook.”
7. WESLEY SNIPES, ACTOR
Wesley Snipes was perhaps the most bankable Black male actor next to Eddie Murphy in the 1990s. Snipes continued to star in feature films in the early part of the millennium, however, he filed for bankruptcy in 2006. That same year, Snipes was indicted for tax fraud for failing to pay over $12 million in taxes over the course of six years.
Snipes was released from prison in April 2013 after serving three years.
6. GARY DOURDAN, ACTOR
Actor Gary Dourdan was a regular on CBS’ popular hit series CSI: Crime Scene Investigation for eight seasons until 2008.
In 2012, Dourdan filed for Chapter 11 protection. Documents obtained by TMZ showed the actor had $1.8 million in assets but owed creditors $1.73 million. Dourdan also claimed that his m
onthly disposable income was only $321.
The former television actor currently has three films in pre-production.
5. DIONNE WARWICK, SINGER
It is unclear how much Warwick has earned over more than five decades in the music industry, but it is known that she had more than 60 charted singles, global album sales totaling more than 100 million copies, two children’s books, a best-selling autobiography, and a fragrance line.
In March 2013, the legendary hit maker, 72, claimed in a federal court filing for bankruptcy that she owes $10.7 million, most of it for taxes.
4. SINBAD, COMEDIAN, ACTOR
The comedian filed for bankruptcy for the second time in April 2013. Sinbad, real name David Adkins, first filed in 2009, but it was dismissed because he did not file the right documents, according to TMZ.
In the second go-round, Sinbad claimed he owed debts of about $11 million, $8 million of which stemmed from back taxes 1998-2006 and 2009-2012.
Sinbad showed little regret for his current financial situation, telling Oprah Winfrey last spring: “I didn’t buy Bentleys. I didn’t live largely. I invested in me. I invested in a lot of other people. I would not change it; I would not go back.”
3. MIKE VICK, CURRENT NFL PLAYER
In 2005, Forbes listed Vick as the world’s fourth-highest-earning athlete. Less than three years later, Vick’s high-flying lifestyle became a thing of the past.
The former Atlanta Falcons quarterback was discovered operating a dogfighting ring in 2007. He served 21 months in prison and filed for bankruptcy in 2008. In addition to the usual extravagant purchases and questionable investments typically made by newly wealthy athletes and entertainers, Vick went bankrupt covering legal fees incurred after the dogfighting scandal.
Vick signed a $10 million contract with the Philadelphia Eagles this past year – which replaced the 6-year, $100 million contracts he signed in 2011.
2. MC HAMMER, ENTERTAINER
MC Hammer became the example for what Black entertainers should avoid after coming into fame. In 1991, Hammer made over $33 million. His spending included luxury cars, airplanes, a record company, the largest entourage in celebrity history, and a $30 million mansion (complete with a bowling alley, 17-car garage, and a baseball diamond).
By 1996, he had amassed $14 million in debt and declared bankruptcy.
Hammer later became a minister, launched a tech startup (a search engine called WireDoo), and in 2012 joined Korean pop star Psy onstage at the American Music Awards for a performance of “Gangnam Style.”
1. MIKE TYSON, HEAVYWEIGHT BOXER
Former heavyweight boxing champ Tyson was once worth $400 million. In 2003, he filed for bankruptcy and was reported $50 million in debt. Last year, Tyson declared he was finally stable: “I’m totally out of bankruptcy.”
For much of 2013, Tyson kept busy with film cameos and a 36-city tour of his one-man show, “Mike Tyson: Undisputed Truth,” written by his wife, Kiki Tyson, and directed by Spike Lee.
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