In the time when Frank Sinatra was in his prime, people didn't really get tattoos unless they were in prison, or they were sailors. Because of that, Sinatra never got the honor of seeing people get his likeness tattooed on them in the same way that modern music and movie stars do, which is a shame. It's a testament to his legacy and enduring appeal that people are doing so now, though, so many years after he died.
As the kingpin of the Rat Pack, Sinatra was pretty much 'the guy' in the 1950s. He was the leading man that film studios wanted for their movies, and when they'd cast him in the film, they wanted him to sing the soundtrack. 'Sinatramania' happened twenty years before the Beatles had even picked up their instruments for the first time to spark 'Beatlemania'. His incredible voice is the sound of a whole era, and although many have impersonated him in the time since, nobody ever did it better than Ol' Blue Eyes.
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.