Sheen reprised his role as Bud Fox in 2010’s Wall Street: Money Never Sleeps, which earned $130 million at the box office. (credit: Ron Galella/Getty Images)
WINNING: GODDESSES
Sheen lives with two women, adult film star Rachel Oberlin “Bree Olson” and Natalie Kenly (right), who seem to adore him. (credit: Jean Baptiste Lacroix/Getty Images)
WINNING: BEAUTIFUL BROOD
Sheen has five beautiful children including a daughter with his high school girlfriend, daughters Sam and Lola with ex-wife Denise Richards and twin sons, Bob and Max, with ex Brooke Mueller. (credit: Donato Sardella/Getty Images)
WINNING: TWO AND A HALF MEN
Although Warner Bros. fired Sheen from top-rated sitcom “Two and a Half Men” on March 7, 2011, he held the Guinness record for “Highest Paid TV Actor Per Episode,” raking in a cool $1.24 million per episode. (credit: CBS/Getty Images)
WINNING: ALWAYS CHARLIE
Sheen is apparently such a winner that his sitcom characters have borrowed his own name. (credit: Michael Caulfield/Getty Images)
LOSING: CUSTODY BATTLES
Sheen and Brooke Mueller are currently battling for custody of their twin sons, Max and Bob. The boys were removed from Sheen’s home in early March. Denise Richards and Sheen had a custody dispute over their two daughters, Sam and Lola, after their divorce in 2006. She is reportedly keeping them away from him due to his erratic behavior. (credit: Ethan Miller/Getty Images)
LOSING: TROUBLE WITH THE LAW
Sheen was arrested in Aspen, Colo., for felony menacing, third-degree assault and criminal mischief in 2010. He pleaded guilty to the assault charge as part of a plea deal. (credit: Aspen Police Department via Getty Images)
LOSING: SHOOTING KELLY PRESTON
In 1990, Sheen accidentally shot his fiancée, Kelly Preston, in the arm. The couple’s engagement was subsequently broken off. (credit: Gabriel Bouys/Getty Images)
LOSING: THREE FAILED MARRIAGES
Charlie Sheen recently split from his wife, Brooke Mueller. He also divorced his first wife, model Donna Peele, as well as his second wife, actress Denise Richards. (credit: Carlo Allegri/Getty Images)
WINNING: HE’S SOBER
In late January, Charlie Sheen announced that he would be undergoing a substance rehabilitation program at his home, a.k.a. Sober Valley Lodge, in Sherman Oaks. (credit: Kevork Djansezian/Getty Images)
WINNING: SPIN CITY
Sheen won the Golden Globe Award for Best Actor in 2002 for his portrayal of Charlie Crawford after he replaced Michael J. Fox on Spin City. (credit: K. Mazur/Getty Images)
WINNING: HE GETS PAID TO TWEET
One of Sheen’s recent tweets advertising an intern position (yes, assisting him) was a paid-for endorsement from internships.com (credit: twitter.com)
WINNING: 2.27 MILLION TWITTER FOLLOWERS
Sheen had one million followers in a little more than a day (a new record) and is steadily gaining more followers. (credit: twitter.com)
LOSING: FIRED FROM “TWO AND A HALF MEN
On March 7, 2011, Warner Bros. Television terminated Sheen’s Services on “Two and a Half Men.” (credit: Chris Polk/Getty Images)
