9 Milestones in the Evolution of Brad Pitt

Meet Joe Black (1998)

Following a gruesome role opposite his then-girlfriend Gwyneth Paltrow in David Fincher's Seven, his first Oscar nomination (for Terry Gilliam's 12 Monkeys) and his banishment from China (because of Seven Years in Tibet), Pitt reunited with Anthony Hopkins in Martin Brest's Meet Joe Black. Boldly playing the role of Death in the most expensive non-special effects movie ever made, Pitt and the three-hour film both received mixed reviews.

Fight Club (1999)

A year later, Pitt reunited with David Fincher for the controversial adaptation of Chuck Palahniuk's novel. Like in 12 Monkeys, the actor explored the psychologically disturbed with his portrayal of Tyler Durden, Edward Norton's uber-violent onscreen alter ego. Pitt flexed his muscles again two years later as a bare-knuckle boxing champ in Guy Ritchie's crime film Snatch.

Mr. & Mrs. Smith (2005)

Six years and one (literally) epic $175 million misfire (Troy) later, Brad Pitt was back in theaters with his most successful romantic comedy to date. After failing to generate much heat with his Mexican co-star Julia Roberts in 2001, Pitt's off-screen chemistry with Angelina Jolie (and the tabloid's interest in his deteriorating marriage) buoyed the film's worldwide box office gross to nearly $500 million.

The Assassination of Jesse James by the Coward Robert Ford (2007)

The previous year, Pitt launched his producing career with the documentary God Grew Tired of Us. A year later, Pitt would enjoy dual credits for the first time as he produced and starred in this limited release Western thriller. Since The Assassination of Jesse James, Pitt's Plan B production company has gained momentum with projects including The Time Traveler's Wife, Kick-Ass and Eat Pray Love.

The Curious Case of Benjamin Button (2008)

For the third time in his 24 year (and counting) career, Pitt reteamed with David Fincher for this effects-heavy drama about a a man who ages in reverse. The actor, who spent his career raising speculation that he would never receive the actor-ly praise he deserves because of his good looks, was finally able to shed the bone structure and body that both boosted his career and detracted from his credibility. Perhaps after this project -- which nullified his good thanks to generous CGI and make-up -- and over three decades worth of improving performances, Brad Pitt will finally be able to win the Oscar that some believe he deserves.

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