Bad Boy Charlie Sheen

1 Ginger Lynn Charlie Sheen — Personal Photo

Well before Charlie Sheen's latest tangle with trouble -- allegedly threatening to kill his wife - the movie star had a long bad boy history that included domestic violence, substance abuse, escorts and porn stars. In the 1990s, he had a long love affair with pornography icon Ginger Lynn, seen here.

2 Heather Hunter Charlie Sheen — Personal Photo

Sheen, born Carlos Irwin Est

03 heidi fleiss Charlie Sheen — Personal Photo

Charlie Sheen's dalliances with women have not always been with long-term girlfriends or wives. In 1993, Sheen utilized the services of Heidi Fleiss, also known as the Hollywood Madam, seen here. Fleiss provided call girls to Sheen at least 27 times costing the actor more than $50,000, Sheen admitted in videotaped testimony.

brittany ashland Charlie Sheen — Personal Photo

In the late 90s, Sheen dated another porn star, Brittany Ashland, seen here. But their relationship went south fast. After Ashland filed a lawsuit claiming Sheen beat her up, threatened to keep her quiet and knocked her unconscious, prosecutors charged him with misdemeanor battery with serious injury. Sheen pleaded no contest and got a one-year suspended prison term and two years probation.

05 kelly preston Charlie Sheen — Personal Photo

Charlie Sheen also dated and intended to wed actress Kelly Preston, seen here. But in 1990, Sheen accidentally shot Preston in the arm. The wound was stitched up. The relationship was not. Preston is currently married to John Travolta.

06 denise richards Charlie Sheen — Personal Photo

Perhaps Charlie Sheen's most talked-about relationship was his 4-year marriage to actress Denise Richards, seen here. After Sheen's Dec. 25, 2009 arrest for allegedly threatening to kill his current wife Brooke Mueller, Richards tweeted "one day..I will spill my guts about EVERYTHING." Richards and Sheen had two kids together. Their bitter divorce played out in the tabloids for years.

SLIDESHOW Brooke Mueller Charlie Sheen — Personal Photo

On Dec. 25, 2009, Charlie Sheen was arrested in Aspen, Colo., for allegedly threatening to kill his current wife, Brooke Mueller, seen here. She told police the "Two and a Half Men" actor pinned her on a bed, put a knife to her throat and threatened to kill her because she wanted a divorce.

08 mugshot Charlie Sheen — Personal Photo

Charlie Sheen, seen here in a booking photo, faces charges of felony menacing, domestic violence, second-degree assault and criminal mischief after he allegedly attacked his wife Brooke Mueller and threatened to kill her with a knife. He was freed on $8,500 bond.

09 ginger lynn facebook 3 Charlie Sheen — Personal Photo

Well before Charlie Sheen's latest tangle with trouble -- allegedly threatening to kill his wife, the movie star had a long bad boy history that included domestic violence, substance abuse, escorts and porn stars. In the 1990s, he had a long love affair with pornography icon Ginger Lynn, seen here

10 ginger lynn facebook Charlie Sheen — Personal Photo

Over the years, Charlie Sheen has battled numerous drug and alcohol problems. On May 20, 1998, Sheen tried injecting cocaine, accidentally giving himself an overdose. He was hospitalized, but discharged from the hospital soon afterward. Martin Sheen issued a statement saying, "This is not an easy moment in our lives, but it's a necessary one." Seen here is Ginger Lynn, a porn star who a relationship with Sheen.

11 heather hunter Charlie Sheen — Personal Photo

Sheen, born Carlos Irwin Est

12 kelly preston Charlie Sheen — Personal Photo

Charlie Sheen also dated and intended to wed actress Kelly Preston, seen here. But in 1990, Sheen accidentally shot Preston in the arm. The wound was stitched up. The relationship was not. Preston is currently married to John Travolta.

Perhaps Charlie Sheen's most talked-about relationship was his 4-year marriage to actress Denise Richards, seen here. After Sheen's Dec. 25, 2009 arrest for allegedly threatening to kill his current wife Brooke Mueller, Richards tweeted "one day..I will spill my guts about EVERYTHING." Richards and Sheen had two kids together. Their bitter divorce played out in the tabloids for years.

14 sheen+wife Charlie Sheen — Personal Photo

Despite telling police that her husband Charlie Sheen threatened to kill her on Christmas Day 2009 in Aspen, Colo., Brooke Mueller, seen here, said she wanted to patch things up. Mueller's lawyer, Yale Galanter, said her client didn't understand that her statement to police would lead to her husband's arrest.

15 ginger lynn Charlie Sheen — Personal Photo

Over the years, Charlie Sheen has battled numerous drug and alcohol problems. On May 20, 1998, Sheen tried injecting cocaine, accidentally giving himself an overdose. He was hospitalized, but discharged from the hospital soon afterward. Martin Sheen issued a statement saying, "This is not an easy moment in our lives, but it's a necessary one." Seen here is Ginger Lynn, a porn star who a relationship with Sheen.

Charlie Sheen's dalliances with women have not always been with long-term girlfriends or wives. In 1993, Sheen utilized the services of Heidi Fleiss, also known as the Hollywood Madam, seen here in a booking photo. Fleiss provided call girls to Sheen at least 27 times costing the actor more than $50,000, Sheen admitted in videotaped testimony.

17 kelly preston Charlie Sheen — Personal Photo

Charlie Sheen also dated and intended to wed actress Kelly Preston, seen here. But in 1990, Sheen accidentally shot Preston in the arm. The wound was stitched up. The relationship was not. Preston is currently married to John Travolta.

18 ginger lynn Charlie Sheen — Personal Photo

Well before Charlie Sheen's latest tangle with trouble -- allegedly threatening to kill his wife - the movie star had a long bad boy history that included domestic violence, substance abuse, escorts and porn stars. In the 1990s, he had a long love affair with pornography icon Ginger Lynn, seen here.

19 denise richards Charlie Sheen — Personal Photo

Perhaps Charlie Sheen's most talked-about relationship was his 4-year marriage to actress Denise Richards, seen here. After Sheen Dec. 25, 2009 arrest for allegedly threatening to kill his current wife Brooke Mueller, Richards tweeted "one day..I will spill my guts about EVERYTHING." Richards and Sheen had two kids together. Their bitter divorce played out in the tabloids for years.

20 Brooke Mueller Charlie Sheen — Personal Photo

Despite telling police that her husband Charlie Sheen threatened to kill her on Christmas Day 2009 in Aspen, Colo., Brooke Mueller, seen here, said she wanted to patch things up. Mueller's lawyer, Yale Galanter, said her client didn't understand that her statement to police would lead to her husband's arrest.