Charlie Sheen’s lawsuit history includes a $100 million wrongful termination case against Warner Bros. Television, two criminal domestic violence prosecutions, prolonged custody and child support fights with both of his ex-wives, and civil claims from former partners tied to his HIV-positive status. Some ended in guilty or no-contest pleas, some in confidential settlements, and at least one remains unresolved as of early 2026.
The Warner Bros. and Chuck Lorre Lawsuit
In January 2011, production of Two and a Half Men was halted after Sheen was ordered into rehab. Instead of entering a facility, he attempted at-home treatment and, in February, went on the Alex Jones Show to attack creator Chuck Lorre, calling him a “clown” and “a stupid, stupid little man” and directing anti-Semitic insults at him.1Us Magazine. Two and a Half Men’s Charlie Sheen and Chuck Lorre’s Ups and Downs2Variety. Two and a Half Men: Chuck Lorre and Charlie Sheen Make Amends In March 2011, CBS and Warner Bros. fired him, citing “dangerously self-destructive conduct” and set tensions.
On March 10, 2011, Sheen filed a $100 million suit in Los Angeles Superior Court against Warner Bros. Television and Lorre. The complaint alleged breach of contract, disability discrimination under California’s Fair Employment and Housing Act, and sought punitive damages. Sheen’s lawyers argued the studio had described him as “manic,” “bipolar,” or “hypomanic” and fired him rather than accommodating those alleged conditions.3The Hollywood Reporter. Charlie Sheen Files $100 Million Lawsuit Warner Bros. pointed to a felony-linked morals clause, a force majeure provision covering incapacity of a principal cast member, and a publicity clause giving the producer control over press.4The Hollywood Reporter. Charlie Sheen’s Contract Was Actually…
The case never reached a jury. In June 2011, a judge ruled the dispute had to go to arbitration under Sheen’s contract.5The Herald. Charlie Sheen Files $100 Million Lawsuit Against Producers On September 26, 2011, the parties announced a confidential settlement.6Deadline. Charlie Sheen, Warner Bros. TV, Chuck Lorre Announce Settlement Sources reported an initial payment of roughly $25 million tied largely to profit participation already owed.7CBS News. Report: Charlie Sheen to Get $25M Settlement Sheen kept his share of syndication profits from roughly 170 episodes, projected as high as $100 million over seven to ten years.8ABC News. Charlie Sheen to Win Settlement From Warner Brothers He later sold those rights for $26.7 million.9The Hollywood Reporter. Charlie Sheen Seeks to Cut $55,000 Child Support
Criminal Cases
1996 Battery of Brittany Ashland
Sheen was arrested at his Agoura Hills home on December 20, 1996, after an altercation with then-girlfriend Brittany Ashland, 24. She alleged he grabbed her by the hair and slammed her onto a marble floor, knocking her unconscious and leaving a split lip that required seven stitches. He was released on $20,000 bail.10CBS News. Charlie Sheen and His Abusive Past: The Case of Ex-Girlfriend Brittany Ashland11Los Angeles Times. Misdemeanor Battery Charge Filed Against Charlie Sheen Prosecutors filed a misdemeanor battery charge with serious injury in February 1997. Sheen pleaded no contest on June 6, 1997, and Judge Lawrence Mira imposed a suspended one-year prison term, two years of probation, $2,700 in fines, 300 hours of community service, and mandatory counseling.12UPI. Charlie Sheen Pleads No Contest
2009 Aspen Domestic Violence Case
Sheen was arrested in Aspen, Colorado, on Christmas Day 2009 after a domestic dispute with wife Brooke Mueller. He was charged with felony menacing, misdemeanor assault, and criminal mischief.13Los Angeles Times. Charlie Sheen’s Troubled History On August 2, 2010, he pleaded guilty to misdemeanor assault; prosecutors dropped the felony and the mischief count. He received 30 days in a rehabilitation center, 30 days of probation, 36 hours of anger management, and a permanent bar on firearm possession.14ABC News. Charlie Sheen Pleads Guilty to Misdemeanor Assault
2010 Plaza Hotel Incident
On October 26, 2010, Sheen was ejected from the Plaza Hotel in New York after causing thousands of dollars in damage to a room. Capri Anderson, whose legal name is Christina Walsh, filed a criminal harassment complaint accusing him of threatening to kill her.15ABC News. Capri Anderson Tells ABC Charlie Sheen Threatened to Kill Her Whether the Manhattan district attorney pursued formal charges is not established in available reporting. Sheen sued Anderson himself, alleging attempted extortion of a seven-figure sum and theft of a Patek Philippe watch valued at $165,000.16CNN. Charlie Sheen Lawsuits
Custody and Child Support Fights
Denise Richards
Denise Richards filed for divorce in March 2005 while pregnant with the couple’s second daughter. In April 2006, she obtained a temporary restraining order alleging Sheen had pushed her and threatened her life; a judge ordered him to stay at least 300 feet from Richards and daughters Sami and Lola, with limited supervised visitation. The divorce was finalized in November 2006.17E! Online. Charlie Sheen and Denise Richards’ Messy History18ABC News. Charlie Sheen and Denise Richards Timeline
In January 2016, Richards filed a $1.2 million claim alleging Sheen had not honored the terms of a trust for their children. In October 2021, a judge granted Sheen’s request to eliminate his child support payments to Richards entirely, effective retroactively to August 2018. By that point, both daughters had moved in with Sheen after a reported falling out with their mother.19People. Denise Richards Blindsided by Charlie Sheen Child Support Ruling
Brooke Mueller
Sheen and Mueller married in 2008 and had twin sons, Bob and Max. In March 2011, Mueller filed for a restraining order and emergency custody, alleging Sheen had threatened to “cut your head off, put it in a box and send it to your mom.”20CNN. Charlie Sheen Custody Dispute A judge removed the twins from Sheen’s home and ordered him to stay at least 100 feet away.21ABC News. Charlie Sheen’s Long List of Legal Woes The following month, the parties reached an agreement giving Sheen the twins every other weekend, with a nanny required at all times initially and three random monthly drug tests for both parents.22Today. Charlie Sheen and Brooke Mueller’s Custody Agreement
In 2016, Sheen petitioned to reduce his $55,000 monthly child support to Mueller, citing a drop in monthly income from more than $600,000 to about $167,000 after the sale of his profit participation rights, and reporting over $12 million in debt.9The Hollywood Reporter. Charlie Sheen Seeks to Cut $55,000 Child Support He then unilaterally cut his payments to $10,000 per month; Mueller froze some of his accounts to recoup $88,000 in arrears, and a court temporarily set support at $10,000 per month for each ex-wife pending further hearings.23San Francisco Bar Association. Charlie Sheen Needs Two and a Half Men to Pay His Child Support
In January 2024, Sheen obtained an emergency order granting him immediate sole custody if Mueller failed or missed a drug or alcohol test. The order also required Sheen to pay Mueller’s rent, subject to termination if she relapsed.24NBC News. Charlie Sheen Granted Sole Custody of Twin Sons25People. Charlie Sheen Granted Emergency Order for Sole Custody
In December 2025, Mueller filed court documents accusing Sheen of owing more than $15 million in unpaid child support and accrued interest, alleging he paid in full only through June 2011 and made no payments during 2012–2015 and 2019–2022.26Cleveland.com. Popular TV Star Owes More Than $15M in Child Support Interest In January 2026, the parties agreed to pause court proceedings to pursue a private settlement, with Sheen committing to provide a detailed financial accounting.27Yahoo Entertainment. Charlie Sheen and Ex to Resolve $15M Dispute
HIV Nondisclosure Lawsuits
Sheen was diagnosed as HIV positive around 2011 and disclosed his status publicly on NBC’s Today show on November 17, 2015, saying he had paid “upwards of $10 million” to people who had threatened to reveal it.28Today. Charlie Sheen Reveals He’s HIV Positive Two civil lawsuits from former partners followed.
Scottine Ross (Brett Rossi)
On December 3, 2015, ex-fiancée Scottine Ross, also known as Brett Rossi, sued Sheen in Los Angeles Superior Court, alleging assault, battery, false imprisonment, and failure to disclose his HIV status during their November 2013 to October 2014 relationship.29CNN. Charlie Sheen’s Former Fiancee Files Lawsuit30Fox 40. Charlie Sheen’s Ex-Fiancee Sues, Alleges Assault, Battery, Failure to Disclose HIV31People. Charlie Sheen: Brett Rossi Sues Him After HIV Revelation32Los Angeles Times. Charlie Sheen Responds to Scottine Ross Lawsuit33Variety. Charlie Sheen Sued for HIV Exposure by Girlfriend The ultimate resolution has not been publicly reported.
Jane Doe
In June 2017, a second ex-girlfriend, identified in court papers only as “Jane Doe” and described as a Russian émigré, sued in Los Angeles County Superior Court. She alleged that when she asked about sexually transmitted infections, Sheen told her he was “fine,” and did not disclose his HIV status until after they had unprotected sex on October 26, 2015.34HuffPost. Charlie Sheen Settles HIV Lawsuit The case settled for $120,000, with resolution papers filed on January 13, 2022, before Judge Theresa M. Traber.35NBC Los Angeles. Suit Against Charlie Sheen Regarding Alleged HIV Exposure Settles
2014 Dental Office Assault Suit
In October 2014, dental technician Margarita Palestino sued Sheen in Los Angeles Superior Court, alleging assault, sexual battery, and intentional infliction of emotional distress. She said that during a September 2014 appointment, Sheen ripped off his nitrous oxide mask, yelled death threats, grabbed her chest area, tried to remove her bra, and threatened a dentist with a knife, allegedly while under the influence of crack cocaine, Theradol, and alcohol.36The Hollywood Reporter. Charlie Sheen Sued for Assault, Sexual Battery Sheen’s attorney called the suit “ridiculous and fictional,” saying Palestino had been fired for disclosing Sheen’s presence to her son, and attributed his behavior to a bad reaction to nitrous oxide.37Courthouse News Service. Woman Claims Charlie Sheen Assaulted Her The plaintiff filed for dismissal, and the case was dismissed in November 2015.38Yahoo News. Lawsuit Dropped: Charlie Sheen Can Now Go Back To…