Downey told the New York Times. The Oscar nominated actor starred as Iron Man between 2008 and 2019, ultimately becoming the world’s top earning actor. It was a dramatic turn around for the formerly incarcerated actor, sentenced to three years in prison in 1999 for cocaine possession charges. He was granted an early release in 2000. ““You could just feel the evil in the air,” he said in another recent interview, referring to his time in prison.