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15 Famous People Who Went From Rags To Riches And Back Again

Celebrity Money
15 Famous People Who Went From Rags To Riches And Back Again

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Popular headlines around the entertainment blogosphere these days suggest: There’s only one thing people like more than a rags-to-riches story and that’s a story about someone losing their riches. We like to celebrate triumph over hardship, but we also really enjoy when the playing field is evened out the other way and rich and famous people defy the odds to lose it all. Whether it’s jealousy or some misplaced sense of justice, people love it when celebrities mismanage their money. Today’s article combines the best of both worlds with stories about people rising to stardom and riches and then losing it all.

Not every rags-to-riches-to-rags story made the cut for this list. For example, Wesley Snipes, songstress Toni Braxton, and comedian Chris Tucker, just to name a few, but their stories are mostly about tax evasion, or drug addiction, and greedy managers, pandering producers, or just friends and/or accountants who gave horrible advice, the usual stuff. The following is a list of people whose stories are a bit more out of the ordinary; entertainers and athletes, politicians and producers who were iconic in their times, whose rise to wealth from rags to riches defied steep odds, or whose fall back to rags was particularly unexpected, weird, tragic, or otherwise noteworthy.

Here are 15 iconic human beings who climbed their way against all odds to the top of the mountain only to tumble right back down. Here are 15 famous people who went from rags to riches and back again.

15. Gary Coleman

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Gary Wayne Coleman was adopted at birth by a nurse practitioner mother and fork-lift operator father and at the height of his success, was earning $100,000 an episode, in 1980s money, for playing an adopted son on the hit sitcom, Diff’rent Strokes.

Over the course of 8 years/seasons, Coleman became a TV superstar and both the actor and his character, Arnold, became known across the U.S. just as much for his catchphrase as for being short and having childlike facial features into adulthood. Most fans were unaware, until his 2010 death, that the actor’s physical traits were the side effect of lifelong treatment of autoimmune kidney disease. Due to these medical expenses, plus shady accountants, a lawsuit against his adoptive parents, and his own irresponsible spending, Gary Coleman struggled financially after his popularity faded and in 1999 filed for bankruptcy.

14. Mickey Rooney

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Millennials and younger folk may only remember Mickey Rooney as the old man who griped about things for a minute or two at the end of the U.S. news program 60-minutes, assuming they remember Rooney or 60-minutes, at all. But, Mickey Rooney is an award-winning actor and comedian who got hist start back in vaudeville times.  At his first audition, his mom couldn’t afford to dye her son’s hair for an ad that called for a dark-haired kid, so she burned some cork, rubbed the ash in Mickey’s hair, and sent him out on stage.

In the late 30s and early 40s, he made millions as a movie star, but upon his death in 2014, his estate was worth a measly $18,000. When Mickey Rooney died, his nine children were angered to find they’d all be nixed from his will, even though one of these 9 “kids”, step-son Christopher Aber, had actually embezzled away most of their father’s fortune.

13. Warren Sapp

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Between 1995 and 2007, Warren Sapp, the Orlando-born, single mother-raised football player was an NFL athlete, so we know how he made his money, but how did this legendary defensive tackle end up over $10 million in debt? From the looks of it, Sapp got himself in debt the old fashioned way, by spending well beyond his means, though committing some felonies and knocking up a few women along the way probably didn’t help.

He filed for Chapter 7 bankruptcy in 2012 while he had over $6 million in assets and a $540k annual salary as an NFL Network employee, and that cash flow still wasn’t enough to keep lawyers, bill collectors, and baby mamas happy (and still afford a real, lion skin rug and 250 pairs of Jordans–these are actual purchases Sapp made). Though the former athlete announced his recent recovery from bankruptcy, he also has some new criminal charges to contend with that might send him right back into debt.

12. Wayne Newton

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This is another name millennials and younger might not be familiar with, but in his heyday, Wayne Newton was better known as Mr. Las Vegas or sometimes just Mr. Entertainment, and was listed in the 1983 Guinness Book of World Records as the highest-paid entertainer of all time. What the record books don’t show is that Mr. Entertainment is a horrible investor and untrustworthy business partner, or that he’s filed for bankruptcy twice since his record-breaking peak. The singer and son of homemaker, Evelyn, and auto mechanic, Patrick Newton, now lives on but does not own his Nevada ranch, Casa de Shenandoah, which has been partially repurposed as a memorabilia museum…that gives tours…through Wayne Newton’s house.

11. Burt Reynolds

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Back before people started growing mustaches ironically and waxing the hair from every part of their bodies, before the VW van + aviator glasses + mustache + thrift store t-shirt combo became associated with creeps, Burt Reynolds was a God among men, a genuine sex symbol.

With a father in the military and later law-enforcement, blue collar Burt intended to become a professional football player after graduating from Florida State U where he had enrolled on an athletic scholarship. Life obviously had other plans for the now-legendary actor whose road has had its ups and downs: After major success as a TV actor in the 70s and 80s, he declared bankruptcy in the mid-90s and, even as recently as 2011, Reynolds faced financial troubles when Merrill Lynch foreclosed on one of his Florida properties.

10. Sinbad

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Eighties comedy sensation and HBO mainstay Sinbad (a.k.a. David Adkins), went bankrupt for the second time in 2013. Adkins explained to Oprah, in a March episode of her talk show, that it was not frivolous spending on material things that ate away the profit from a respectable stand-up and sitcom career. He has remained vague about what exactly keeps draining his finances, hinting that needy, flaky family and friends are the culprit, but remains optimistic, telling Oprah, “It’s never over.”

Sinbad’s appearance on The Apprentice followed on the heels of his first bankruptcy in 2009, but his boss Donald Trump, fired him before he could leverage the show and himself out of financial ruin. It’s no secret that Sinbad comes from poverty, what few know is he was discharged from the U.S. Air Force or that while he was on Trump’s show he was also listed as one of the 10 least tax-compliant citizens in California, owing the state $2.5 million.

9. M.C. Hammer

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If you’re anything like me, you’ll be surprised to know that MC Hammer‘s last track dropped in 2011, but in the early 90s, the world couldn’t get enough of the rap superstar. Hammer was born Stanley Kirk Burrell in east Oakland, CA, and was raised by his single mom alongside eight siblings. By contrast, at the height of his success, Burrell employed close to 200 people, many to maintain a $12 million mansion.

Sadly, just 6 years after his 1990 hit “U Can’t Touch This” helped sell him 18 million albums, MC Hammer was $13 million in debt; he had to sell the mansion for a fraction of its value and ditch the extravagant life along with his gold parachute pants. MC Hammer has also appeared on Oprah to explain his money situation. Unlike most celebs on this list though, Hammer also told Oprah that he’s financially stable again (as a tech investor), making his a story of rags to riches to rags and back again.

8. Willie Nelson

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Born in small-town Texas during the Great Depression, Willie Nelson could not have come from more humble beginnings. One would think that this arena-filling grassroots musician lost his fortune to marijuana-related legal troubles but, though he’s had plenty of botanical issues, it was financial negligence at the hand of a long time manager that decimated Nelson’s fortune. For years, his manager failed to pay Nelson’s taxes, which led the IRS to claim the folk legend owed them $32 million in back taxes and seize the entirety of his assets in 1990. Combine tax evasion with periodic run-ins with the law, it’s no wonder the country rebel’s money disappeared

7. Suge Knight

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Recording mogul and thug entrepreneur, Marion “Suge” Knight seems bent on staying behind bars and, as of mid-2015, is in jail. Knight has a lengthy arrest record and is notorious for using physical intimidation to negotiate business deals. As godfather of west coast rap, he founded Death Row Records to release still-influential works like Dr. DRE’s Chronic. Fun fact: Suge and his entourage allegedly roughed-up Vanilla Ice to get him to sign over royalties for his hit, “Ice Ice Baby.” In 2009, legal fees and an out-dated dependence on mafia business strategy led Knight into insolvency.

(Runner up: Orenthal J. Simpson. OJ Simpson gave his fortune to defense attorneys to beat a murder rap and paid the rest in damages to his alleged victims’ families. Just like Knight, Simpson has filed for bankruptcy and is currently incarcerated.)

6. Michael Jackson

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Michael Jackson filed for bankruptcy in 2007, after defaulting on his $25 million Neverland Ranch mortgage. The deceased King of Pop failed to realize that debt matures, no matter how hard a debtor fights not to. By now we all know the story of M.J.’s upbringing and the Jackson household: Ruled over by a physically abusive and overzealous father-manager named Joe, if Michael wasn’t practicing his song and dance or being violently disciplined, he was being exposed at an inappropriately early age to backstage debauchery. Jackson’s irresponsibility may have stemmed from this early over-stimulation but more likely comes from just never being taught how to balance a check book.

5. Meat Loaf

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Marvin Lee Aday, better known as the recording artist Meat Loaf, Marvin Aday was raised in the conservative South mostly by his grandmother, away from his abusive alcoholic father, and grew up to be one of the best selling musicians of all time at 80 million units sold worldwide to date. He had a similar experience to Willie Nelson when he discovered his management was mismanaging his money. As opposed to Nelson, Meat Loaf’s manager was plainly embezzling (rather than racking up back taxes). In 1981, with his record label getting anxious over a lull in the operatic rocker’s popularity, Aday fired his label-appointed managers and the record label sued for breach of contract and froze his assets, forcing the recording artist $1.6 million into debt.

4. Mike Tyson

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Mike Tyson earned over $400 million over the course of his boxing career, and through overspending, but mostly due to an expensive divorce and legal fees paid to criminal defense lawyers, in addition to an exploitative manager with questionable ethics, was forced to file for bankruptcy in 2003.

About 20 years after what was arguably the height of his reign as heavyweight champion, how the mighty had fallen, and that’s not mentioning a sexual assault conviction and jail time that fans would sooner forget. Given his felonious past, and because he’s a biter in the ring, it’s hard to feel sorry for the boxer-turned-actor now only worth $1 mill before taxes.

3. Ulysses S. Grant

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The victorious general of the Union army and, later, 18th President of the United States, Ulysses S. Grant started life on a farm and as the son of a tanner. After winning a war and the race for President, he surely was financially stable for a time, but after stepping down from office this carpetbagger lost most of his money speculating on Wall Street.

(Runner up: Abraham Lincoln. Before going into politics, Lincoln had bailed on several bad investments and even filed for bankruptcy. Though the 16th U.S. President was free from financial woes once he became a lawyer then a politician, historians would argue he bankrupted an entire region of the country he presided over and lived in.)

2. Dennis Rodman

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Dennis Rodman is allegedly one of 47 other children born to the perfectly named Vietnam vet and rolling stone, Philander Rodman, Jr. Over fifty years later, Philander’s son was last seen checking back into rehab, with his own mountain of overdue child support payments to deal with.

Alcoholism and three divorces on their own are not what make Dennis Rodman’s descent from a successful career in the NBA as fascinating as a horror movie you know you should but can’t look away from; it’s more the very public nature of his stints in rehab (on Celebrity Rehab with Dr. Drew), who he’s divorced (model Carmen Electra), his increasingly pierced and bizarre outward appearance, and of course his recent trip to North Korea. In the end, Dennis Rodman made it so high up this list, because he is the only famous person on here who has less than zero dollars to his name.

1. Samuel Clemens/Mark Twain

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Mark Twain tops this list mostly because nobody would expect the biting satirist and brilliant author to be downright stupid when it comes to finance and investment, but lack of business sense seems to have run in the Clemens family. Samuel was not only born to a father with debt and no luck as an entrepreneur, but he was also born prematurely and was sickly for the first decade of his life. With the odds stacked against him even living long enough to become the literary force he did, Twain followed in his father’s footsteps and after achieving success promptly put himself into debt through a series of ill-advised investments.

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