'Killing Them Softly' Star Brad Pitt: Review His Movie Career in 10 Clicks (GALLERY)

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For the last 20-plus years, Brad Pitt has defined himself as one of the most reliable and successful leading men in Hollywood.

Beginning in 1991, when he quite literally charmed the pants off of Geena Davis in Thelma and Louise, Pitt has made us laugh, cry and, in the case of Fight Club, a little scared, with roles in movies that are sometimes blockbusters, sometimes comedies -- but always unique.

This Friday, he'll do it all over again in Killing Them Softly, in which he plays an enforcer who tries to stop three men from destroying a Mob-run card game.

So, in honor of that, Celebuzz is taking a look back at 10 key moments in Pitt's Oscar-nominated career, from his high notes (Seven; Moneyball) to his hook-up with wife-to-be Angelina Jolie (Mr. & Mrs. Smith) and his, uh, let's just say that Troy happened and leave it at that.

Check it out now in the gallery, above.

Killing Them Softly is now playing in theaters nationwide.

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