At one stage, Charlie Sheen was Hollywood's highest paid TV actor.

The main star of comedy series Two and a Half Men, Sheen was making an eye-watering US$1.8 million (NZ$2.8m) per episode in the show's final season in 2011, before being sensationally axed and replaced by Ashton Kutcher.

Worth US$150m (NZ$235m) at his peak, Sheen's current net worth is estimated to be less than US$10m (NZ$15.7m).

And a new legal bid against the star, launched by his ex-wife, Denise Richards, alleges just what he has done with his millions.

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"(Sheen) squandered over $US24,000,000 (NZ$37.6m) from the sale in his interest in Two and a Half Men to pay his personal debts and to support his extravagant lifestyle at the expense of support payments for his children," court documents claim, according to E! News.

Sheen, who revealed he was HIV positive in 2015, says he previously paid extortionists millions of dollars to keep the diagnosis a secret. Photo / Getty Images
Sheen, who revealed he was HIV positive in 2015, says he previously paid extortionists millions of dollars to keep the diagnosis a secret. Photo / Getty Images

Richards, who is the mother of Sheen's two daughters, alleges he owes her nearly half a million dollars in child support.

"During the time frame since our last stipulation/order in 2016, he has failed to pay $450,000 (NZ$704,610) in support while diverting over $600,000 (NZ$939,480) in assets to adult family members and converting thousands of dollars into cash for his own personal use," the court documents also state.

But Sheen is not taking it lying down, labelling Richards a "coward", telling The Blast the court documents were "fiction".

"D and her legal posse traffic only in fiction. My day in court is painfully overdue," Sheen said. "She is behaving like a coward and the truth will prevail."

Sheen's expenditure has been well documented in the media, especially after his axing from Two and a Half Men.

Last year several US media outlets reported he had spent up to US$400,000 (NZ$626,300) on prostitutes per year in the 1990s.

In 2012, a source told RadarOnline he would pay a single sex worker up to US$25,000 (NZ$39,000) for one night, while also showering them with expensive gifts.

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Sheen revealed in 2015 he was HIV positive, admitting he had previously paid extortionists about $10 million (NZ$15.7m) to keep the diagnosis a secret.

There were also reports in 2012 he was spending $2000 (NZ$3131) per day on drugs.

Sheen, who has been in and out of rehab, has been very open about abusing alcohol and drugs over the years.

"It feels awful. I can't sit here and lie to you. Some of it is very surreal. To this day, I'm not sure how I created such chaos and wound up in that head space," he said in a recent interview on Loose Women.

"It's as though there was some alien or demonic possession going on . . . I wish I could make a lot of it go away, but they wouldn't call it the past if it wasn't."

Denise Richards and Charlie Sheen, pictured together in 2005. Photo / Getty Images
Denise Richards and Charlie Sheen, pictured together in 2005. Photo / Getty Images

Sheen and Richards, who were married in 2002 before divorcing in 2006, have been embroiled in several ugly legal fights over the years, but seemed to have mended their relationship.

Only a few months ago Richards discussed their ongoing friendship and ability to co-parent on the latest season of the Real Housewives of Beverly Hills.

In August 2018, Charlie filed court documents asking to modify his child support payments to Richards and his other ex, Brooke Mueller.

He said his income had "changed significantly" and claimed he couldn't meet the current child support payments.

"I have been unable to find steady work, and have been black-listed from many aspects of the entertainment industry," he claimed in the documents.

"All of this has resulted in a significant reduction in my earnings."

He added he was "willing and able to provide child support", but not at the level currently required.