Charlie’s Craziest Controversies

Credit: Vianney Le Caer/Invision/AP/Shutterstock

Charlie's Craziest Controversies

A look back at the highest-paid TV actor's troubled past

Credit: Ron Galella/WireImage.com

1990

His engagement to actress Kelly Preston is called off after he accidentally shoots her in the arm.

Credit: Jordan Strauss/WireImage.com; Mark Sullivan/WireImage.com

1995

He admits dropping $50,000 on call girls working for famous Hollywood Madam Heidi Fleiss.

Credit: AP Photo/Bob Marshak/JBPR

1995

Two months after wedding model Donna Peele (above), he is sued by a UCLA student who accused him of striking her after she refused him sex. The case is settled out of court.

Credit: James Aylott/Getty Images

1997

He pleads no contest to a charge of battery with serious bodily injury after model Brittany Ashland alleges he smashed her face on the kitchen floor.

Credit: AP Photo/Nick Ut

1998

He is sent to rehab after his father, West Wing star Martin Sheen, tells the court his son has overdosed on cocaine.

Credit: Eric Charbonneau/BEI

2002

Mere months after wedding Denise Richards, she alleges that he is gambling and abusing prescription drugs. She claims he even spray painted "the dumbest day of my life" on their wedding pic and pushed her around. Their marriage ends in 2006.

Credit: MAVRIXONLINE.COM

2009

Less than two years after wedding Brooke Mueller, he is arrested for roughing her up during a Christmas Day spat, in which he threatened her with a knife: "If you tell anybody, I'll kill you."

Credit: Alexandra Wyman/WireImage.com

2010

He is ordered to 30 days in rehab after pleading guilty to a misdemeanor assault charge in his domestic violence case involving Mueller.

Credit: Jeff Rayner/Coleman-Rayner

2010

Reports claim he donned sunglasses and a 'stache to hide from photographers because he's having an affair with a lingerie model. His reps says he was just joking around.

Credit: Shutterstock (3)

2018

The actor claimed that he could no longer afford his child support payments to ex-wives Denise Richards and Brooke Mueller after claiming he was “blacklisted” by Hollywood in court documents obtained by Us Weekly at the time. Sheen noted that his “income has changed significantly” since 2016, when he was ordered to pay a total of $20,000 to Richards for their children Sam and Lola, and $55,000 to Mueller for their kids Max and Bob.

Credit: Shutterstock (2)

2018

After Roseanne Barr came under fire for her controversial tweet about Valerie Jarrett that led her to be fired from the Roseanne revival, Sheen said he understood what she was feeling. “I can relate to that tone of absolute despair because it’s not just about herself, it’s about the people that she knows she affected as well,” he said during an interview on Australia’s Kyle and Jackie O show. “What I hear in her voice, trying not to focus on the words but the emotion, is I hear the frustration, pain. There’s a sadness there.”

Credit: PENNY STEPHENS/EPA-EFE/Shutterstock

2019

Years after Sheen’s character was killed off of Two and a Half Men, he told Us exclusively that he’d love to get closure. “I would do it today,” he said, before explaining he thinks he would be well-received by fans. “Just what I hear in the street, how much people would embrace that. I haven’t been in touch with anybody [from the show].” Sheen was fired in March 2011 after he made derogatory comments about the series' creator Chuck Lorre.