Jamie Lynn Szantyr, better known by her wrestling moniker, Velvet Sky, is one of those homegrown wrestling acts that you can't help but love despite her being a heel character. Velvet Sky has been apart of two collective groups that have dominated in multiple organizations including The Beautiful People alongside Madison Rayne and Lacey Von Erich and The Allure including Angelina Love and Mandy Leon. While Velvet Sky isn't particularly athletic, she's a great performer and can execute one hell of a Headscissor.
The Connecticut-native got her start in the sport by way of World Xtreme Wrestling (WXW) in 2004. Then Szantyr made a few appearances in the WWE the following two years. Her peak popularity came when she was on the TNA roster from 2007-2011. Sky made brief stops throughout the independent circuit including stints in Mexico's Lucha Libre AAA Worldwide and promotion companies in Puerto Rico before making her way back to TNA. Throughout her career, Sky has racked up some belts including the TNA Women's Knockout Championship (2x), TNA Knockouts Tag Team Championship (1x), TNT Women's Championship (1x), and more. While she says her in-ring days are a wrap, she currently is under contract with Ring of Honor (ROH).
Not all celebrities have fame and fortune, some are just famous – and in a ton of debt. They came from rags to riches, then went back to rags. Whether they’ve filed bankruptcy, ended up in court, or just can’t stop spending, celebrities mismanage their money just like everyone else. They just hide it well.
50 Cent coined the term “wanksta,” then “partied like it was his birthday” until he filed Chapter 11 bankruptcy in 2015. The rapper was said to be anywhere between $10 million and $50 million in debt. In 2016, a federal bankruptcy court judge in Connecticut approved a plan for the founder of G-Unit to pay his debts back. He was able to get his bankruptcy discharged in February of the following year.
Following a 45-year-long career in Hollywood, acting in more than 70 films, actor Gary Busey found himself in more debt than he was worth. In 2012, it was reported that Busey owed between $500,000 and $1 million worth of debt, but only had $50,000 to his name. The 74-year-old actor owed money to hospitals, banks, the L.A. Waterworks District, and even a storage company. He filed Chapter 7 bankruptcy that same year. Despite his longstanding career in Hollywood, Busey's net worth is now only $500,000.
Burt Reynolds is still worth five million dollars, but his battles with debt date back more than 20 years. Between bad investments and a pricey divorce from actress Loni Anderson, the 1970s superstar had to deal with over $10 million in debt and decided to file Chapter 11 bankruptcy in 1996. While testifying in a 1994 custody hearing, the South Florida native said he spent $40 million getting through his divorce.
The former Hollywood bad boy, Charlie Sheen owes the IRS nearly $5 million. But that's not all. In 2016, his net worth was reportedly still as high as $150 million, but he was nonetheless $12 million in debt at the time – including mortgages, legal fees, and taxes. That same year, Debt.com reported Sheen owed nearly $300,000 on an American Express card alone.