When The Checks Stop Coming In: Broke Celebs

Money comes and money goes, which is cool when you’re talking about $5 or $10. But these stars made millions and millions of dollars and somehow managed to spend even more.

For more on megastars who went broke, check out Moguldom’s latest documentary, When The Checks Stop Coming In.

Allen Iverson

When Allen Iverson stepped into the NBA, he was nicknamed “The Answer.” Although he never won an NBA championship, he will go down as one of the greatest point guards to ever dribble a basketball. But Iverson has always made as many headlines off the court for his legal woes and financial difficulties. Even though at one point he was making $20 million per season, Iverson has spent up much of his money. He frequently traveled with an entourage that rivaled MC Hammer’s crew. In 2012, he admitted in court documents that he pulled in $62,500 a month but had to shell out $360,000 in expenses, with most of it going to creditors and mortgage payments.

MC Hammer

MC Hammer became the poster child for what not to do when you make it big. In 1991, he made over $33 million alone but he also bought a $30 million mansion complete with a bowling alley, 17-car garage and a baseball diamond, countless luxury cars, airplanes, and a record company, plus he had one of the biggest entourages in hip-hop history. Even Jay Z poked fun of the bankrupt MC in “So Appalled,” rapping “And Hammer went broke so you know I’m more focused/ I lost 30 mil, so I spent another 30/ Cause unlike Hammer, thirty million can’t hurt me.”

Chris Tucker

In 2007, Chris Tucker became the highest paid actor in Hollywood thanks to his $25 million check for starring in “Rush Hour 3.” Three years later, the IRS was knocking at his door for the $11 million in back taxes he owed. The “Friday” star was forced to sell three mansions, two in Florida and one in L.A., to pay back Uncle Sam. After taking a long sabbatical, Tucker went back to work by performing stand-up all across the country. He also returned to making movies and received acclaim for his performance in the 2012 flick “Silver Linings Playbook.”

Wesley Snipes

Wesley Snipes branded himself as one of Hollywood’s biggest Black action stars, and though he’s made a lot of cash, the “Blade” star blew right through his money and we all learned about it when he filed for bankruptcy in 2006. Although it’s not known exactly what Snipes was spending his money on, it clearly wasn’t o paying the IRS because that same year he was indicted on tax evasion charges. Owing $12 million, Snipes failed to pay the IRS for six years. He spent three years in prison and following his release, his good buddy Sylvester Stallone got him a role on “The Expendables 3.”

Terrell Owens

Terrell Owens was one of the best wide receivers in the game and he was certainly paid handsomely for his efforts. The former San Francisco 49ers made over $70 million during his careeer but he has little to show for it. Owens has been plagued with money woes and it has gone from bad to worse in recent years. Forced to sell several of his high-priced homes well under market value, the future Hall of Famer also had to shell out $50,000 a month in child support to four different women. And on top of that, he was hit with a half a million-dollar tax lien. After a failed attempt to play arena football, Owens has unsuccessfully tried to get back into the NFL.

Toni Braxton

There’s no denying Toni Braxton’s talents. The legendary R&B singer has sold over 40 million albums worldwide. But despite that, she still had to file for bankruptcy twice. The first time came in 1998 because of a one-sided contract with LaFace Records. The second time came more than a decade later when the “Unbreak My Heart” singer was forced to back out of a very lucrative residency at Las Vegas after she was diagnosed with lupus. Since then, Braxton has seemed to get her finances in order. She currently stars on a reality show with her sisters, which she executive produces and she recently wrapped up a tour with fellow singer Babyface.

Tionne “T-Boz” Watkins

TLC made headlines in 1995 when they infamously filed for Chapter 11 Bankruptcy but Tionne “T-Boz” Watkins found herself in bankruptcy court again when her finances fell apart in 2011. Saddled with medical bills for treatment for a brain tumor and sickle cell anemia, T-Boz lived off of her royalties for years. She tried to file yet again last year but a judge dismissed her case because she made no attempts to settle her debts. Her Honda Odyssey minivan was repossessed as well.

Mike Tyson

Evander Holyfield isn’t the only boxer who made millions and then cried broke. “Iron” Mike Tyson had his opponents shaking in their boxing trunks from fear and his many knockouts have earned him $400 million. But in 2003, Tyson filed for bankruptcy saying he was $50 million in debt. Since then, Tyson threw himself into work. He made numerous cameo appearances in movies and on television shows and last year he embarked on 36-city tour of his one-man show. His efforts paid off because last year he declared he was debt free.

Sinbad

Most celebrities are too embarrassed to admit they’ve mismanaged their money and would shy away from discussing their finances. But Sinbad had no problems opening up about how he lost his money. Last year the “Houseguest” star filed for bankruptcy citing $11 million in debt with more than $8 million of it from back taxes owed. While other celebs balled out of control at the shopping malls, Sinbad blamed his lack of money on something else. “I didn’t buy Bentleys,” he said in an interview with Oprah Winfrey. “I didn’t live large. I invested in me. I invested in a lot of other people. I would not change it; I would not go back.”

Gary Dourdan

We first laid eyes on Gary Dourdan as Freddie’s boyfriend, the pro-Black Shazza Zulu on “A Different World.” And then he popped up as Janet Jackson’s love interest in her “Again” music video. Since then, the Philadelphia native has starred in the original “CSI” crime series for eight years. But even though he had $1.8 million in assets, Dourdan filed for bankruptcy in 2012 claiming that his monthly disposable income was only $321 and he owed more than $1.73 million to creditors.

Dionne Warwick

After five decades in the music industry, Dionne Warwick has accomplished a lot including selling 100 million albums worldwide, penning two children’s books and a best-selling autobiography as well as launching her own fragrance line. But despite all of this, the “That’s What Friends Are For” singer still had a problem handling her finances and last year she had no other choice but to file for bankruptcy. Warwick owed more than $10.7 million to creditors.

Warren Sapp

Warren Sapp was one player quarterbacks did not want to go up against. The former Tampa Bay Buccaneers defensive tackle was voted into the NFL Hall of Fame the first year he was eligible but despite his accomplishments on the field, Sapp may be most remembered for how he mismanaged his money. Two years ago, he filed for bankruptcy and court documents showed that even though he had $6.45 million in assets, he owed creditors $6.7 million. Some of his assets included a $1,200 lion skin rug and an Air Jordan collection worth $6,500, which may help explain why he’s had problems managing his money.