As the third of actor Martin Sheen’s children and brother of brat packer Emilio Estevez, the king of second chances grew up living the charmed life in Malibu. His first film appearances were alongside dad in “Badlands” and “Apocalypse Now” before he could legally drive. It wasn’t long before he dropped out, became a teen dad with to daughter Cassandra and starred in a string of blockbusters including Red Dawn (1984), Platoon (‘86), Wall Street (’87), Young Guns (’88), Major League (’89), Hot Shots (’91) and The Three Musketeers (’93). It didn’t take long for “The Machine” to deadfall from the top. The ‘90s were a blur of porn star girlfriends and prostitutes (He spent $53,000 in 15 months with Madam Heidi Fleiss.), epic partying, failed engagements (Kelly Preston ended things after being accidentally shot.) and marriages, legal troubles (no contest to battery of model Brittany Ashland), and stints in rehab (including a court-ordered lockdown detox after a drug overdose). His first comeback came in 2000 when he took over for Michael J. Fox on Spin City, a gig that earned him a Golden Globe in 2002, the same year he married Denise Richards. In 2003, he moved on to Two and a Half Men, becoming the highest-paid TV actor by season 8. After having two daughters, Richards divorced Sheen in 2005 claiming he gambled and abused pills. By 2009, he was remarried to Brooke Mueller and father to twin boys, but that relationship ends in misdemeanor assault charges, a return to partying and hookers and another bitter custody battle. By 2011, the personal troubles seeped into the professional, resulting in public attacks on his Men bosses, his firing, lawsuits and a tour to capitalize on his Twitter notoriety and “winning” catchphrases. Claiming to be cured again, Sheen returned to TV in 2012 with Anger Management.
Charlie Sheen Search Results
Birthday BoyA natural born "Hotshot," Charlie Sheen turns 46 on Sept. 3, so in his honor we go from A to Z on all things Charlie.
winning 'doCharlie Sheen compliments Miley Cyrus' new look on Twitter.
Sin City SinnersWhose out-of-control antics in Las Vegas got them in big trouble? Find out!
Friendly ExesDenise Richards hosts a birthday party for Brooke Mueller that is attended by Charlie Sheen.
Poetic or Not?In honor of Bad Poetry day, click through to cast your vote on whether stars like Beyonce and Ed Westwick are poetic or not at all.
Halle's MoveHalle Berry tries to move to Paris and more celeb news in The Shortlist.
Oops!Take a look back at some of the most memorable celeb mistakes and mishaps.
Over It?Do these stars deserve second chances after their slipups? Vote now!
New SuitA police captain who was demoted for providing Charlie Sheen with an escort has sued his department.
Major PledgeCharlie Sheen commits to donating $1 million to the USO.