Tropic Thunder (2008)

Tropic Thunder allowed Downey to take a major creative risk — playing a daffy Australian actor, Kirk Lazarus, who undergoes surgery to play an African-American character in a war movie.

Downey joked at his Santa Barbara International Film Festival career retrospective that he knew either he would get in trouble for the role, or Ben Stiller — who wrote, directed and starred — would get in trouble for playing an actor who becomes “Simple Jack,” a mentally challenged man, in desperate pursuit of an Oscar. Downey joked in Santa Barbara that he emerged unscathed, and that Stiller took the bigger hit.

Oscar voters seem to have gotten what Downey was doing: He was nomiated for Best Supporting Actor.