- 1Sheen and real estate agent Brooke Mueller married in 2008 and welcomed twin sons a year later. But in December 2009, Sheen was arrested for domestic violence before both he and Mueller entered rehab for substance abuse. They tried to make it work for a few more months, before ultimately divorcing in late 2010.
Brooke Jaye Mueller is an American actress. moremore ABOUT
- Age: 38
- Birthplace: Albany, New York, United States of America
- Profession: Real Estate Broker, Actor
- Credits: A Love Song for Bobby Long, Witchouse, Strictly Sexual, The Possessed
- 2Sheen's tumultuous relationship with his second wife was tabloid fodder for years. The two married in 2002, and welcomed their daughter Sam in 2004. But when Richards was six months pregnant with their second daughter, Lola, in 2006, she filed for divorce and asked for a restraining order. Richards claimed that Sheen brought prostitutes to their home, gambled illegally, and created an unstable environment for their children.
Denise Lee Richards is an American actress and former fashion model. She has appeared in films, including Starship Troopers, Wild Things, Drop Dead Gorgeous, The World Is Not Enough as a Bond girl, and in Valentine. She played Monica and Ross Geller's cousin on Friends. From 2008 to 2009, she starred on ...moremore ABOUT
- Age: 44
- Birthplace: Downers Grove, Illinois, United States of America
- Profession: Television producer, Model, Actor
- Credits: Starship Troopers, The World Is Not Enough, Wild Things, Valentine
- 3Before she went on to marry John Travolta, Kelly Preston was engaged to Charlie Sheen. The two got together after divorce from Kevin Gage in 1987. They stayed together until 1990, when Sheen accidentally shot (!) Preston in the arm with a loaded shot gun he had in his pocket.
Kelly Preston is an American actress and former model. She has appeared in more than 60 television and film productions, most notably including Mischief, Twins and Jerry Maguire. She is married to John Travolta. moremore ABOUT
- Age: 53
- Birthplace: Honolulu, Hawaii, USA
- Profession: Model, Actor
- Credits: Jerry Maguire, Twins, Death Sentence, For Love of the Game
- 4Robin Wright was one of Charlie Sheen's first girlfriends. The two dated as teenagers from 1981 t0 1982, when they were both breaking into the business.
Robin Gayle Wright is an American actress and television director. She was previously credited as Robin Wright Penn. Wright first gained attention when starring in the NBC soap opera Santa Barbara as Kelly Capwell from 1984 to 1988, for which she received three Daytime Emmy nominations. She made the ...moremore ABOUT
- Age: 49
- Birthplace: Texas, USA, Dallas
- Profession: Spokesperson, Businessperson, Film Producer, Model, Actor, + more
- Credits: The Princess Bride, Forrest Gump, House of Cards, Santa Barbara
- 5Sheen dated actress Brittany Ashland in the late '90s, but the couple's relationship ended violently in 1997. Sheen pleaded no contest to misdemeanor battery charges after grabbing Ashland by the hair and slamming her head into their marble floor during an argument at home. Ashland was hurt so badly that her split lip required seven stitches. Sheen was sentenced to a a one-year suspended prison term and two years probation.
- 7Sheen may have briefly dated the most famous madam in Hollywood history in 1988. He famously testified against her at her 1995 trial for tax evasion and pandering. He admitted to spending more than $50,000 on her prostitutes.
Heidi Lynne Fleiss is an American former madam, and also a columnist and television personality regularly featured in the 1990s in American media. She ran a prostitution ring based in Los Angeles, California, and is often referred to as the "Hollywood Madam". moremore ABOUT
- Age: 50
- Birthplace: Los Feliz, Los Angeles, California, United States of America
- Profession: Pimp, Journalist, Author, Actor, TV Personality
- Credits: The Doom Generation, Celebrity Rehab with Dr. Drew, Celebrity Rehab Presents Sober House, Celebrity Big Brother, Porndogs: The Adventures of Sadie, + more
- 8Sheen and Ryder dated in the late '80s after starring together in the 1986 movie Lucas. Soon afterward, Ryder hit the big time with 1988's Heathers.
Winona Ryder is an American actress. She made her film debut in the 1986 film Lucas. As Lydia Deetz, a goth teenager in Tim Burton's Beetlejuice, she won critical and popular recognition. After various appearances in film and on television, Ryder continued her acting career with the cult film Heathers, ...moremore ABOUT
- Age: 44
- Birthplace: Minnesota, United States of America
- Profession: Actor, Voice acting
- Credits: Edward Scissorhands, Black Swan, Girl, Interrupted, Dracula
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