Ranking The 30 Best Actors of All-Time

26. Sean Penn

Image Source: Independent

From his breakout performance as beloved stoner Jeff Spicoli in Fast Times at Ridgemont High to his award-winning efforts as a dramatic actor, Sean Penn has had a remarkable journey. For over 35 years on screen, Penn has acted in more than 50 films (and directed four others). Considered one of the finest actors of his generation, Penn’s streetwise simmer and wounded-animal core evoke the best of Brando and De Niro. He creates a character with infinite attention to detail. Penn won the Academy Award for Best Actor in a Leading Role for Mystic River (2003) and Milk (2008).