By the time Charlie Sheen tied the knot with Brooke Mueller in 2008, he had already experienced a whirlwind of dramatic romances and marriages.

Back in 1984, a young 19-year-old Charlie welcomed his daughter, Cassandra, with his high school sweetheart. A few years later, he became engaged to actress Kelly Preston. However, their relationship came to an abrupt end following a tumultuous incident where Charlie accidentally shot her in the arm.

Sheen’s first official marriage was in 1995 to Donna Peele, but this union was short-lived and ended the following year.

His second marriage was with actress Denise Richards, spanning from 2002 to 2006, during which they had two daughters, born in 2004 and 2005.

As Sheen’s divorce proceedings with Richards were wrapping up in late 2006, he met Brooke Mueller, a real estate investor and part-time actress, through their mutual friend Rebecca Gayheart. Charlie and Brooke exchanged vows in May 2008. Less than a year later, in March 2009, they celebrated the arrival of their twin sons, Bob and Max.

However, by 2010, cracks in their marriage began to show, exacerbated by Sheen’s public breakdowns, stints in rehab, and increasingly unpredictable behavior. In May of that year, Sheen relinquished his joint legal custody of his daughters to Richards, who had long pursued sole custody due to his struggles with sobriety and the tumultuous nature of their previous relationship.

In November 2010, Mueller filed for divorce. Their turmoil escalated on March 1, 2011, when the couple’s twins were removed from Sheen’s home by police after social services received a report from Mueller stating, “I am very concerned that [Charlie] is currently insane.” At the time, Sheen was living with several adult film actresses, including Bree Olson, whom he referred to as his “goddesses,” during the peak of his highly publicized “winning” media spiral.

The instability continued for years. In May 2013, Charlie and Brooke’s twins were temporarily placed in Denise Richards’s custody after child protective services intervened again.

Needless to say, the last two decades of Charlie Sheen’s family life have been extraordinarily chaotic, marked by cycles of custody battles, addiction struggles, legal disputes, and ongoing financial conflict. And it’s not over.

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When Charlie and Brooke got together, he was the king of television thanks to “Two and a Half Men.” His work on the show made him the highest-paid television actor in the world. When you include backend syndication points, in the show’s later seasons, Charlie earned $2 million per episode. In a 24-episode season, that meant Charlie was earning around $48 million per year.

In March 2011, right around the time when Brooke reported that she was concerned that he was “currently insane,” Charlie was fired from “Two and a Half Men” after getting into a public spat with the show’s creator, Chuck Lorre.

Three months after his firing, Charlie and Brooke finalized their divorce. According to the terms of their settlement, Charlie paid Brooke a one-time fee of $750,000 and agreed to pay her $55,000 per month until their sons turned 18. At the time, their boys were two years old. The $55,000 monthly payments were supposed to last through March 2027.

Unfortunately, according to a court filing made by Brooke last week, Charlie apparently stopped making his $55,000 monthly payments shortly after their divorce agreement was signed. Brooke’s filing claims Charlie owes an amount “totaling $8,967,600” not including interest. If you divide $8,967,600 by $55,000, you get 163. As in, Charlie reportedly hasn’t paid support in 163 months. That roughly puts his last payment at roughly May 2012. As in, exactly one year after their divorce was finalized.

That’s not all.

Brooke’s court filing further claims that Charlie owes $6,418,643 in interest for the alleged unpaid child support. For a total debt of $15,386,243.

Denise Richards has had similar payment issues with Charlie over the years. In 2019, Denise filed documents alleging Charlie owed her $450,000 in unpaid child support. In a filing at the time, Denise further claimed that Charlie squandered a one-time windfall of $24 million from the sale of his ownership in “Two and a Half Men.” Money that was supposed to help him get squared on their debt.

Perhaps due to their financial woes, in 2022, Denise and Charlie’s eldest daughter, Sami Sheen, made headlines when she joined OnlyFans. Denise followed her daughter to OnlyFans soon thereafter. When Denise was going through a divorce in 2024, it was revealed that she makes around $250,000 per month, a large portion of which presumably comes from OnlyFans.

Charlie, who once boasted a net worth of $150 million, has claimed to be in a “dire financial crisis.” Charlie came very close to foreclosure on at least one occasion before finally selling a longtime mansion at a steep loss. He briefly moved in with his parents and now rents a condo in Malibu for $16,000 a month. It’s nearly impossible to peg his net worth today, especially given his reported massive debts. FYI. Child support can not be wiped out in bankruptcy. Charlie has not responded to Brooke’s filings as of this writing. If and when he does, we will report back.