How Charlie Sheen Moved From Highest-Paid Actor on TV To Almost Homeless

Fans of Charlie Sheen know that his reputation as a bad boy was the inspiration for his role as Charlie Harper on Two and a Half Men. While his alcoholism and drug abuse as portrayed by the show would have been a call for help, it skyrocketed Charlie Sheen’s wealth as he became one of the highest-paid actors in the world.

Sadly, the delicate balance needed to tell his story on Two and a Half Men and his terrible impulses could only be maintained for so long, an infamous meltdown on the set of the show led to one of the biggest falls from grace in Hollywood’s history.

Today, Charlie, who lived in some of the most expensive mansions in Hollywood now finds himself in danger of being homeless through late mortgage payments and rising debt. Find out how it all went down here.

Charlie Sheen’s Wealth and How He Lost It All

In his final season of Two and a Half Men, Charlie Sheen cemented his place among the highest-paid actors of all time. It was reported that he earned as much as $1.8 million per episode, with $1.3 million coming in as salary with an additional $600,000 in backend deals.

It was the gig of a lifetime but his relationship with drugs, liquor, and women combined with a perceived conflict with the show’s producer, Chuck Lorre, led to his dismissal from the show.

Although Charlie Sheen was still very popular enough to secure another lucrative role in another show, Anger Management, where he reportedly maintained his status as one of the world’s highest-paid actors through a contract that saw him earn as much as $2 million per episode, it was not enough to keep up with his very expensive personal life.

Despite his earnings from Two and a Half Men and the $125 million he bagged as a settlement after his dismissal from the show, the actor was hemorrhaging a lot of money for various reasons and it was only a matter of time before he runs out of money. From what we gathered, the man was paying as much as $110,000 per month to his two ex-wives and was paying a further $500,000 per year in child support for his kids.

Charlie Sheen’s wealth began to depreciate after he was fired from Two and a Half Men in 2011. By 2016, it was reported that he was in a debt of $12 million, most of which were due to his mortgages.

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Following the end of his time on Anger Management, he was unable to secure lucrative gigs as an actor, and his monthly earnings dropped from $600,000 to $167,000. With that, he lost his status as one of the highest-paid actors in the business.

How He Became Almost Homeless

Despite losing his position as one of the highest-paid actors, Charlie Sheen continued with his frivolous spending and apart from his legal responsibilities to his ex-wives, the actor spent millions on prostitutes just as his drug and alcohol addiction gulped more millions.

Charlie Sheen highest paid actor
Charlie Sheen with one of his ex-wives, Denise Richards

In 2013, he reportedly spent $1.6 million on prostitutes, paying as much as $20,000 per session. He also spent $410,000 per year on his personal chef, $130,000 on parties, $135,000 on clothing and $105,000 on hotels.

On prostitutes, he is believed to be one of the best clients of the celebrity pimp, Heidi Fleiss. He reportedly spends an extra $10,000 to have sex with hookers without condoms aside from the standard fee of $10,000.

The actor was diagnosed with HIV in 2011, but he did not make it public until 2015, and between 2011 and 2015, he reportedly spent $10 million on those blackmailing him about it. He also allegedly bought multiple houses for girlfriends who were aware of his status.

Charlie Sheen’s wealth continued to depreciate as his earnings continued to drop, this inspired a revision of his spousal support payments to his ex-wives in 2018. While he no longer has to pay $110 thousand in monthly payments, he continues to pay $25,000 to both ex-wives.

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Today, the man who was once the highest-paid actor on TV is owing millions in mortgages. In fact, there was a time he was on the verge of being homeless as he was found to be six months behind on his payments.

Since he was diagnosed with HIV, Charlie Sheen has also been spending as much as $25,000 per month on medical expenses. With such heavy spending, it is not difficult to see how the once-celebrated actor has fallen into financial hard times; nosediving from a net worth estimated at $150 million to only $10 million. Thankfully, the actor has been on a path of reformation and he may yet reclaim his lost glory.

Adeola Seun
Adeola Seun
Seun is a CCNA certified graduate of FUTA. He has been writing on various subjects that include finance, economics, celebrity net worth, lifestyle, biographies and politics for over 7 years, Other than writing, he enjoys movies, video games, and sports


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