5. Sean Penn
One of the most outspoken and controversial actors out there, Sean Penn also happens to be one of the most talented. Sean Penn broke out in the early 1980's with his role in Fast Times at Ridgemont High but he became one of the world's most respected actors later in the 90's with his Oscar nominated role in Dead Man Walking. After two more nominations for Sweet and Lowdown and I am Sam, he went on to win his first Oscar for his dazzling performance in Mystic River, where he played a reformed gangster who's daughter is murdered. A few years later, Penn again won Best Actor for his portrayal of real life politician Harvey Milk. Penn is known best for his fiery, intense acting roles but is capable of playing a variety or roles as he showed in Carlito's Way, the Thin Red Line and the Tree of Life. In addition to his acting ability. Penn has also proved to be an extremely capable director making such acclaimed films as the Indian Runner, the Crossing Guard, The Pledge, and Into the Wild. While he currently has no films in production right now, Penn is clearly one of the most intense, versatile, and talented actors in Hollywood.