20. Rosie O'Donnell and Michelle Rounds

20. Rosie O'Donnell and Michelle Rounds

Rosie O'Donnell has been a gay icon on a huge scale ever since she came out in 2002, stating proudly that she was a 'dyke', and she had no idea why people make such a huge fuss about sexuality. Since then she's lent her voice to hundreds of pro-gay causes, always making a point to stand up whenever she sees someone being oppressed.

The story of her marriage is a cute one with a sad ending. She met Michelle Rounds in Starbucks and immediately took a liking to her, and they became engaged after only a few months of dating in December 2011. Six months later they married in a private ceremony, going on to adopt a daughter in January 2013. The relationship didn't last, and they separated in 2015. This was O'Donnell's second same-sex marriage; her first came in San Francisco in 2004 but was annulled by the state when it reversed its stance on the issue later in the same year.

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Did You Know...

I

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.

II

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.

III

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.

IV

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.

V

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.

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