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Charlie Sheen turns 50: 5 times his movie characters were 'winning'

Off the set, Sheen has had his troubles and oddities, but some of his cinematic characters have had their share of "winning" moments.
/ Source: TODAY

Celebrating his 50th birthday Thursday, Charlie Sheen has played quite a few film characters who were "winning" — long before his 2011 utterance of that word became a brief cultural phenomenon. breaks down five of his most "winning" characters from the movies, in chronological order of their release.

1. Boy In Police Station in "Ferris Bueller's Day Off" (1986)

Charlie SheenParamount Pictures

On the surface, Sheen's Boy In Police Station (yes, that's how the character's listed in the credits) is losing: He's there because of "drugs." He's making misogynistic assumptions about his own sister and Ferris Bueller's sister Jeanie (played by Jennifer Grey), based solely on their use of eye makeup. If he weren't wearing a black leather jacket, it might as well be a well-tailored red flag. And yet, by the time Mrs. Bueller returns from her discussion with local law-enforcement authorities, Jeanie and BIPS can't keep their hands off each other. Confidence for the win.

2. Bud Fox in "Wall Street" (1987)

Charlie Sheen plays Bud Fox in "Wall Street."20th Century Fox

Bud Fox is destined for a downfall in "Wall Street," but not before he lives the high life and turns the tables on his former idol, Gordon Gekko (Michael Douglas). "Greed is good," Gecko claims. And if that's the case, both he and Fox are winning … until they aren't.

3. Ricky "Wild Thing" Vaughn in "Major League" (1989)

Charlie Sheen plays Ricky "Wild Thing" Vaughn in the movie "Major League."Paramount Pictures via Everett Collection

Given his odd disposition, criminal past and tendency to throw pitches that are "juuuust a bit outside," Ricky Vaughn earns the nickname Wild Thing, which becomes a term of endearment as the Indians start to change their losing ways en route to winning the American League pennant. (Sheen also played a real-life pennant winner, Oscar "Hap" Felsch, in 1988's "Eight Men Out," but that story doesn't have a happy ending for the 1919 Chicago White Sox players accused of fixing the World Series.)

4. Topper Harley in "Hot Shots!" (1991)

Charlie Sheen plays Topper Harley in the "Top Gun" spoof "Hot Shots!"20th Century Fox

Many of Sheen's characters have depended on firearms to defend freedom overseas (1986's "Platoon"), freedom in their own backyard (1984's "Red Dawn") and a Wild West posse (1988's "Young Guns"), but few did so with the broad humor and overall ridiculousness of fighter pilot Topper Harley in this slapstick parody of 1986's "Top Gun." Making people laugh, for the right reasons? Win.

5. Aramis in "The Three Musketeers" (1993)

Charlie Sheen plays Aramis in Walt Disney Studios' "The Three Musketeers."Walt Disney Studios

"All for one, and one for all!" Sheen dropped the gun in favor of an épée in his portrayal of the legendary Aramis, one of three chivalrous swordsmen who vow to protect and serve the king of France. Selfless behavior isn't always easy, but it doesn't get more winning than that.

Follow writer Chris Serico on Twitter.