7 Milestones in the Evolution of Robert Downey Jr.

Chaplin (1992)

Downey's earned his first Oscar nomination for his portrayal of the legendary silent-film actor and director. Of course, he had no chance of winning against Al Pacino for Scent of a Woman, Denzel Washington for Malcolm X and Clint Eastwood for Unforgiven (Downey did win the BAFTA award for Best Actor), but the film marked the crest of the first half of Downey's career. Unfortunately, he was about to take a huge step off a cliff into addiction, numerous jail stints and borderline unemployability. He vented his frustration to Toback in a 1997 Movieline interview: "I thought The Pick-Up Artist would give me a chance to have a real career, and it didn't turn out that way. When I did Chaplin I thought, 'Well, this has got to do it!' But it still didn't happen. It still hasn't happened. It really pisses me off. But I have to say, I haven't been in a film that's been a ... a hit. And I guess that's the game."

Kiss Kiss Bang Bang (2005)

After a roughly 10-year period marked with minor ups (Wonder Boys, The Singing Detective) and bitter downs (losing his Ally McBeal gig after a 2001 drug arrest), Downey climbed back for good in Shane Black's indie Kiss Kiss Bang Bang. Produced by Downey's eventual wife Susan (they met on the Gothika set in 2003), the dark crime comedy reinvigorated critical and commercial interest in Downey, opening the door for his higher-profile turns in The Shaggy Dog, Good Night and Good Luck, Zodiac and... well, you know.

Iron Man (2008)

Two films and $1.2 billion in worldwide grosses into the Marvel franchise, Downey is the superstar leading man he envisioned to Toback over a decade ago. Hard to believe that status rests squarely on the shoulders of a billionaire weapons scion named Tony Stark. (Not to mention, to a not-very-lesser degree, a downmarket, Golden Globe-nominated private eye named Sherlock Holmes.)

Tropic Thunder (2008)

Downey earned his second Oscar nomination playing Kirk Lazarus, the Method actor-gone-mad whose full-body transformations earned him a mantel full of industry awards -- providing the meta material for Downey to earn his own nomination as a white actor playing a black military grunt. Were it not for Heath Ledger, he might have even won. Asked about one interviewer about the model for the role, Downey replied, "Sadly, my sorry-ass self." Here's how he did it (clip NSFW):

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