42. Debra Messing

42. Debra Messing

What is it with all these time travelers? Do we have to add Debra Messing to our list now, too? If anything, she looks younger now than she did on her prom night! That's not a sleight against her prom night photo either; she just looks fantastic for her age. Looking at the image on the left though, we have to wonder if she went to the same school as Courtney Cox. Perhaps they even lived close to each other, were best friends, and swapped fashion tips. They've ended up going for the same outfit strategy.

Again, we feel like we might be losing the finer details of this outfit to the black and white picture. It looks like it's all white, but it's also possible that it's a combination of white and another light color. The overall style of the dress is 70s, but the shoulder pads just scream 80s, so this is Messing bringing two eras together!

NEXT

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.

NEXT


Copyright © 2025 CultureHook