The former Anger Management star, 52, filed requests to modify his child support payments to Denise Richards and Brooke Mueller in court documents obtained by PEOPLE
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Charlie Sheen is having a rough time paying child support for four of his children.

The former Anger Management star, 52, filed requests to modify his child support payments to Denise Richards and Brooke Mueller in court documents obtained by PEOPLE.

Sheen, who shares two daughters with Richards and twin sons with Mueller, claims he can’t afford to make his monthly payments because he’s “been unable to find steady work, and [has] been blacklisted from many aspects of the entertainment industry.”

The actor claims he’s had a “significant reduction” in his earnings, and is in a “dire financial crisis” with less than $10 million to his name. The document also lists several debts Sheen has been unable to pay because of his finances, including both a pool service and a gardening service which are both noted as “past due.”

Sheen married Richards in 2002 and they separated in 2006. They share daughters Sam, 14, and Lola, 13. He married Mueller in 2008 but the two split in 2011 — they have sons Max and Bob, 9. The actor also has a 33-year-old daughter, Cassandra Jade Estevez, from a previous relationship with his high school girlfriend Paula Speert.

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In 2010, Sheen was the highest-paid actor in television, raking in $1.8 million per episode of Two and a Half Men. In January 2011, the CBS sitcom went on hiatus after he entered rehab.

Shortly afterward, the actor was fired from the show after a public meltdown that included insulting the show’s creator Chuck Lorre.

In April 2018, Sheen was reported to have nearly $5 million in unpaid taxes for the year 2015, according to court documents obtained by The Blast at the time.

The following month, the actor pitched an idea for a reboot on Twitter after Roseanne was canceled in the wake of a racist tweet by its star Roseanne Barr.

“Adios Roseanne! good riddance. hashtag NOT Winning. the runway is now clear for OUR reboot,” he tweeted adding the hashtag #CharlieHarperReturns and a photo of a script.

Jon Cryer, Sheen’s costar on the long-running CBS comedy, retweeted the post with a message: “What could possibly go wrong?”

In February, Sheen listed his Beverly Hills estate for $9,999,999. The expansive, Mediterranean style home is located in the gated community of Mulholland Estates and features 8,932 square feet of living space, including 7 bedrooms and 7 baths.

Sheen has largely remained under the radar in recent years after going public with his HIV diagnosis in November 2015.