The words “rich” and “famous” seem natural next to each other. But many famous Americans athletes, artists, and entertainers have gone from being millionaires to being broke — and sometimes back again.
“It might make you feel better to know that many famous people before you have had financial hardships,” says Lori Pollack, executive director of the Association of Credit Counseling Professionals, a trade group for people who help people get out of debt.
“To say that with perseverance financial hardships can be overcome is an understatement,” she says. “These individuals and many others did not let their hardships stand in the way of their ultimate successes.”
Pollack and Debt.com compiled this list of celebrity debt featuring people who made it, lost it, then got it back. Check it out, and keep reading for more details about how they did it…
10. Suge Knight
The founder and CEO of Death Row Records signed some of the 1990s’ most famous rappers. But he went to prison in 1996 for violating probation (on a 1992 assault) and when he emerged four years later, his record label was in shambles: Dr. Dre and other stars had left, and Tupac was dead. He declared bankruptcy in 2006, and then started another record label that’s still struggling.
Net worth today: $200,000
Lesson: If you break the law, don’t violate probation.
9. Mike Tyson
The heavyweight world champion blew a $300 million fortune during his career. After legal troubles including a rape conviction, he filed for bankruptcy in 2003 and retired from boxing in 2005. Last year, he wrote a memoir and makes occasional appearances in movies like 2009’s The Hangover.
Net worth today: $1 million
Lesson: Sometimes even the most talented people have to start over in a new career.
8. MC Hammer
The rapper’s release of Please Hammer Don’t Hurt ‘Em, which still stands as the best-selling rap album of all time, earned him $33 million in 1991 alone. But by 1996, he had spent it all — and $14 million more. He filed bankruptcy in 1996 and today makes his living as an ordained pastor. He still owes the IRS $800,000.
Net worth today: $1.5 million
Lesson: Taxes will eventually catch up with you, but the IRS will work with you on a payment schedule.
7. Lauryn Hill
Last year, the singer-songwriter served three months in prison for not paying federal income taxes. The former Fugees “femcee” owed the IRS $500,000 — and signed a $1 million deal with Sony Music to release a new album and pay off her debt. She released a single called “Consumerism” the day she got out of prison.
Net worth today: $2 million
Lesson: Even after you go to prison for not paying your taxes, you still owe those taxes.
6. Annie Leibovitz
The photographer known for celebrity portraits (like a naked John Lennon clinging to Yoko Ono) went broke when several life-changing events hit all at once: Her mother, father, and partner Susan Sontag all died at nearly the same time, and she had twins through a surrogate mother. She also renovated three properties in the Manhattan West Village. She narrowly avoided bankruptcy in 2009, after putting up the entirety of her photographic collection for collateral on a loan.
Net worth today: $20 million
5. Willie Nelson
The country singer owed $32 million in back taxes and worked out an unusual deal with the IRS. He recorded an album called Who’ll Buy My Memories? (The I.R.S Tapes) in 1992 and agreed to pay the government from its sales. After album sales totaling $3.6 million, and $9 million paid from other sources over the next five years, Uncle Sam forgave the rest.
Net worth today: $15 million
Lesson: Settling tax debt can be as creative as it is confusing. Best to consult an expert.
4. Cyndi Lauper
Lauper declared bankruptcy in 1981 after a record with her band Blue Angel flopped, the band fired its manager, and the manager sued for $80,000. The ’80s pop icon worked in retail and thrift stores like NYC’s “Screaming Mimi’s” until she paid it off. Her 1983 album “She’s So Unusual” eventually sold more than 20 million copies.
Net worth today: $30 million
Lesson: If you’re in debt, don’t give up. Suck it up.
3. Larry King
The eventual CNN host racked up $350,000 in debt in the 1970s and was arrested in 1978 for allegedly stealing $5,000 from a business partner. King was acquitted, but the scandal almost cost him his career as a reporter for various local media stations in Miami. At the time of his retirement from CNN in 2010, he had set a world record for the longest-running show with the same host in the same time slot.
Net worth today: $150 million
Lesson: Life isn’t fair, but you shouldn’t let that stop you.
2. Martha Stewart
Stewart was charged with insider trading of pharmaceutical stocks in 2003. After spending five months in prison, her company’s stock plummeted and experts doubted it would survive. But Stewart emerged from a prison and rebuilt her brand.
Net worth today: $970 million
Lesson: People will forgive mistakes and reward hard work.
1. Donald Trump
The Donald’s companies declared bankruptcy four times — in 1991, 1992, 2004, and 2009. The creator of The Apprentice was totally broke more than once, and multiple times had to have his personal finances managed by banks who took over his loans.
Net worth today: $4.1 billion
Lesson: Try, fail, try again, fail better.
CHECK OUT THESE RELATED STORIES