Sean Penn is unquestionably one of the greatest living actors, and someone who Hollywood has been keen to reward for his contributions to the industry. Penn already has two Academy Award wins on his resume thanks to his victories in the Best Actor category for Clint Eastwood’s grizzly crime thriller Mystic River and Gus Van Sant’s heartbreaking historical drama Milk; the stark differences in the two films’ tones speak to Penn’s versatility as an actor.
From Gangster Squad to Racing with the Moon to At Close Range, these 10 Sean Penn movies are arguably his most underrated.