Denise Richards And Charlie Sheen's Messiest Moments

Denise Richards and Charlie Sheen didn't immediately spark a romance when they co-starred in "Good Advice" in 2000. However, fate led their paths to cross again in 2001 when Richards guest-starred in Sheen's show "Spin City," and they started dating shortly after. Their relationship moved at breakneck speed as Sheen popped the question a mere three months after their courtship began. While speaking to People, Richards recalled that the proposal happened right before they were about to sleep on Boxing Day, so her beau was wearing pajamas.

The "Ferris Bueller's Day Off" actor tied the knot with his partner in June 2002 and went on to welcome their first child, Sami Sheen, in May 2004. During a 2023 appearance on "Just B With Bethenny," she shared that their lives were going well around the time because Sheen had joined "Two And A Half Men," which she had urged her husband to take on the part instead of going for another show like he had originally intended.

While the "Wild Things" actor was six months pregnant with their second baby in 2005, she abruptly filed for divorce, citing irreconcilable differences. However, the estranged couple was reportedly working towards fixing their marriage after welcoming their second daughter, Lola Rose Sheen, in June 2005. Ultimately, Richards and Sheen continued their legal proceedings and finalized their divorce in 2006. Despite their separation, the couple continued to stir up drama through the years, and it all seemed to start with the reason for their divorce.

Charlie Sheen's divorce from Denise Richards reportedly happened for several disturbing reasons. Court documents shared by People revealed that the model accused Sheen of physical and mental abuse. They also alleged that the "Wall Street" actor had been suffering from substance abuse issues after welcoming his first child. Richards claimed that Sheen hinted he would physically endanger her if she dared to go public about his drug abuse and even threatened to kill her.

One alleged instance of a death threat occurred when Richards caught her then-husband supposedly looking at "very young girls" on pornographic sites. According to Richards' account, when she brought up the topic, Sheen pushed her and warned her that if she told anyone what she witnessed, she "[wouldn't] lay [her] head down at night." She also alleged that a few days later, he pushed her while she was holding their infant daughter and told her that "he was going to have [Richards] killed." Sheen vehemently denied his estranged wife's claims.

The "Real Housewives of Beverly Hills" alum also spoke about their highly-publicized divorce during her appearance on the "Divorced Not Dead" podcast. "The behind-the-scenes stuff was way worse than what was out there," she admitted. Richards recalled trhing to keep herself together through the abuse for the sake of her daughters but later came to a realization, which she recalled: "I said to myself, would I want my daughters to be married to this man?" (via Today). 

If you or someone you know is dealing with domestic abuse, you can call the National Domestic Violence Hotline at 1−800−799−7233. You can also find more information, resources, and support at their website.

After Charlie Sheen and Denise Richards called it quits, they continued co-parenting their two daughters and spent some holidays together. However, even those small interactions proved to be problematic sometimes. During an episode of the "Real Housewives of Beverly Hills," Richards a particularly bizarre Thanksgiving get-together, "Charlie came over for Thanksgiving for dinner a few years ago, and he had a hooker in the car in the driveway," she confessed. 

"He was afraid to tell me. 'Uh, you know, well, she's in the driveway. Is it okay if she's in the driveway?' I said, 'Ugh. I'll set a f***ing plate,'" Richards explained. The former spouses shared another strange interaction when Sheen visited her home for dinner during a 2012 Rolling Stone interview. When Richards wasn't in the room, the actor started complimenting her looks and then alluded to them having sex on post-divorce family trips. Earlier in the night, Richards expressed that her ex-husband was a wonderful person at the start of their marriage because he was sober. 

Sheen didn't seem to take it as a compliment and repeatedly asserted that he was woefully uninteresting without drugs. At the start of the interview, "The World Is Not Enough" star stressed that she and Sheen were on great terms, but things didn't seem that way a few years later. For Father's Day 2015, Sheen took to X, formerly known as Twitter, to rant about his ex-wife, calling her a "terrorist" and a "heretic washed-up piglet Shame pile" and harshly criticized her acting (The Hollywood Reporter).

In January 2016, Denise Richards sued Charlie Sheen for $1.2 million. According to court documents obtained by People, the "Starship Troopers" star and her daughters had moved into a house close to Sheen upon his request. She alleged that her ex-husband had assured her he wouldn't leave them without a home if things went south, but that's exactly what happened. Richards claimed that after Sheen evicted her and their children, he didn't offer any financial support to help them find a new home. 

The $1.2 million Richards aimed to get from the lawsuit was reportedly for buying a new home. The model also shelled out a whopping $15,000 a month in rent because of Sheen's alleged decision to evict them. To make matters worse, "The Three Musketeers" star is also believed to have sent texts to his young daughter that used disgusting language to describe their mother and preach about his greatness. 

Things took a darker turn as Richards supposedly heard her ex threatening their 10-year-old, "I'm going to kill you and I'm going to kill your mom." Sheen's lawyer, Marty Singer, condemned the lawsuit to E! News, saying, "It is disappointing that Denise Richards always tries to use the children to get more money for her." He further alleged that the mother-of-three had previously bought a $7 million property from his client's money. 

Charlie Sheen allegedly failed to pay $450,000 in child support to Denise Richards, per court documents shared by Us Weekly in 2019. The records detailed, "[Charlie] has squandered over $24,000,000 from the sale of 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." While Sheen reportedly failed to financially support his kids, he had showered his other family members with $600,000 worth of assets.

A year before the filing came to light, Sheen had attempted to reduce the amount he had to pay in child support. Sheen seemed to be realistic about his Hollywood future after years of chaos as he claimed that he couldn't pay $75,000 a month and nearly 10% of his gross annual income to his ex-wives. The actor reasoned he wasn't frequently landing roles because of his tarnished image. He claimed that while his income dwindled, his million-dollar debts continued to mount.

In October 2021, the Los Angeles County Court ruled that the "Anger Management" actor wouldn't have to shell out any money towards child support from August 2018. A source claimed to Entertainment Tonight that Sheen hadn't produced a child support payment to Richards for about four years. They further alleged that Sheen had moved the court date around a handful of times before sneakily landing on a time when Richards was busy working, adding, "Denise was never served this court date."

Charlie Sheen and Denise Richards' eldest, Sami Sheen, is all grown-up and stunning. After she turned 18 in 2022, she started an OnlyFans account. Her choice has reportedly strained her parents' relationship even further. Charlie released a statement to E! News asserting that he didn't actively support his daughter's decision. He also seemed to have made a dig at Richards' parenting style as he wrote, "She is 18 years old now and living with her mother. This did not occur under my roof."

The "Love Actually" actor defended herself in a statement, writing, "This decision wasn't based on whose house she lives in," she noted. "All I can do as a parent is guide her and trust her judgment, but she makes her own choices." "The Bold and The Beautiful" alum later underlined her support for her daughter through an Instagram post. She stated that neither she nor Sheen should feel embarrassed by Sami expressing her sexuality because she had gone down a similar path by working with Playboy in her heyday. 

While speaking on the "Just B" podcast, she revealed that Charlie seemed to have warmed up to his daughter's choices after he saw the tremendous wealth she had accumulated from OnlyFans. Earlier in the year, a source told People that Sami's decision to label herself a "sex worker" had caused more familial problems, but Richards believed she was only doing it to get a rise out of her dad.