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

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

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.

14 Mickey Rooney

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.

13 Warren Sapp

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.

12 Wayne Newton

11  11. Burt Reynolds

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.

10 Sinbad

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."

9 M.C. Hammer

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.

8 Willie Nelson

7 Suge Knight

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.

6 Michael Jackson

5 Meat Loaf

4 Mike Tyson

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.

3 Ulysses S. Grant

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.

2 Dennis Rodman

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.

1 Samuel Clemens/Mark Twain

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