History Lesson: Stars Who Played Historical Characters
Benicio del Toro in Che (2008)
The Puerto Rican actor played iconic Argentine revolutionary Che Guevara in the four-hour film. The accomplished actor won rave reviews for his role as the Marxist leader, but didn't receive an Oscar nod. Sean Penn famously said, "I don't understand. That is such a sensational movie, Che. Benicio is f-----g good in it. And the fact that I'm not running into these people on this awards-party circuit, it's crazy." Regardless of getting no love from the Academy Awards, Del Toro's Che is considered one of the best portrayals of the icon to date.