1980s

Malibu Prince

Sheen, the third of actor Martin Sheen and Janet Estevez's four children, grows up in Malibu, Calif., where he excels in baseball at Santa Monica High School. Though he shows talent on the field, "I just couldn't get it together," he tells PEOPLE of his lackluster academic performance. "The problem is my parents bought me a car when I was 16, and L.A. was at my feet." Sheen soon drops out and follows his dad and older brother Emilio into acting.

1984

Charlie Sheen

August 10

Breaking 'Dawn'

Sheen battles for his big break as Patrick Swayze's younger brother in the war film Red Dawn, which tops the box office during its opening weekend. That December, the 19-year-old actor becomes a father when high school girlfriend Paula Profitt welcomes daughter Cassandra.

1986

Charlie Sheen

Going to Battle

After a string of lighthearted teen movies (Lucas, Ferris Bueller's Day Off), Sheen ships off for Oliver Stone's Oscar-winning Vietnam War drama, Platoon. "When he arrived for filming, Charlie was still a nerd," the director says of his star, whom he put through two weeks of boot camp in the Philippines. "Then each week there was a perceptible change as he became a soldier." Sheen reunites with Stone in 1987 for Wall Street, opposite Oscar winner Michael Douglas. ''Those movies were so hard to make," Sheen tells USA Today. "You age a certain amount in a Stone movie.''

1989

Charlie Sheen

April 07

A Winning Pitch

Now a box office draw, Sheen plays a hard-living, hard-throwing pitcher (dubbed "Wild Thing") in the highly successful baseball comedy Major League. The film, which tops the box office two weeks in a row, spawns the 1994 hit sequel Major League II, with Sheen reprising his blockbuster role.

1990

Charlie Sheen

Parting Shot

Sheen proposes to actress Kelly Preston, but the pink sapphire diamond engagement ring can't hold the couple together when the actress is bizarrely hit with shrapnel in her wrist and ankle by a loaded gun left in one of Sheen's pants. "It was just one of those stupid accidents," he tells Movieline. "It should've happened to me. She was an innocent bystander.'' That same year, he briefly checks into rehab for "extreme exhaustion" and moves on with adult film actress Ginger Lynn Allen. "When he's drinking and using," Allen says, "he's out of control."

1995

Charlie Sheen

July

Heidi's Client List

Tales of the actor's hard-partying ways are solidified when he testifies during Heidi Fleiss's tax-evasion trial. In a videotaped deposition, Sheen – who earned the nickname "The Machine" for his insatiable appetite for drugs, alcohol and women – admits that he spent $53,000 for "sexual services" from the famed Hollywood madam's prostitutes over a 15-month period between 1991 and 1993.

Charlie Sheen

September 03

Charlie Gets Groomed

After meeting on the set of a Japanese commercial in the spring, Sheen, 30, marries model Donna Peele, 25. "She's an angel sent from heaven to take me through the rest of my journey," he says. Over a year later, Peele and Sheen divorce in November 1996, with the troubled actor saying, "You buy a bad car, it breaks down."

1997-1998

Charlie Sheen

Troubled Times

Sheen pleads no contest to a charge of battery after girlfriend, model Brittany Ashland, accuses him of smashing her face on the kitchen floor. "I hope that for his good and everybody else's, he decides to change his behavior," Ashland tells the court through her attorney. The following year, he's hospitalized for a drug overdose, which is in violation of his parole. The actor is given an added year's probation and sent to lock-down detox followed by treatment at Promises rehabilitation center in Malibu. "Pray for my boy, he has appetites that get him into trouble," his father Martin pleads on his behalf.

2000

Charlie Sheen

October 18

Spin City

When Michael J. Fox resigns from the sitcom Spin City to battle Parkinson's disease, a sober Sheen, 35, steps in during the fifth season as deputy mayor Charlie Crawford, opposite Heather Locklear. "To get a shot at getting back in the game with something at this level of exposure, this level of quality, with this amount of talent, is really a blessing," the actor says of his "second chance," which earns him a Golden Globe for best comedic actor in television in 2002.

2002

Charlie Sheen

June 15

Hello, Denise

After meeting on the set of the indie flick Good Advice in 2000, Sheen, 36, and Denise Richards, 31, – who begin dating after the actress makes an appearance on Spin City in 2001 – marry in an outdoor wedding at the Brentwood, Calif., estate of Spin City creator Gary David Goldberg. "I respect him for who he is," the bride tells PEOPLE of her groom's troubled past. "I admire him for where he's come from."

Photo Credits

BIOGRAPHY (top to bottom): Everett; Everett; Diamond Images/Getty; Globe; Ron Galella/WireImage, Jim Smeal/WireImage; Bob Marshak; Jim Ruymen/Landov; Everett; Eric Charbonneau/BEI

Name
Charlie Sheen
Real Name
Carlos Irwin Estevez
Date of Birth
September 03, 1965
Birth Place
New York, N.Y.
Relationships
Brett Rossi, fiancée (2013 to present)
Natalie Kenly, ex-girlfriend (2011)
Rachel Oberlin, ex-girlfriend (2011)
Brooke Mueller, ex-wife (2008 to 2011)
Denise Richards, ex-wife (2002 to 2006)
Brittany Ashland, ex-girlfriend (1996)
Donna Peele, ex-wife (1995 to 1996)
Stephanie Seymour (briefly dated in 1992)
Ginger Lynn Allen, ex-girlfriend (1990 to 1995, on and off)
Kelly Preston (1990, engaged)
Dolly Fox, ex-girlfriend (dated in mid-1980s)
Paula Profitt, ex-girlfriend (1983 to 1984)
Children
Cassandra, daughter (12/12/1984)
Sam, daughter (3/9/2004)
Lola, daughter (6/1/2005)
Max, twin son (3/14/2009)
Bob, twin son (3/14/2009)
Advertisement
Edited by Julia Wang

Charlie Sheen

Celebrity Central / Top 25 Celebs

 

From Our Partners



Sign up for our daily newsletter and other special offers.
    Choose your newsletters
Thank you for signing up! Your request may take up to one week to be processed.
    see all newsletters