Top 10 Best Sean Penn Movies

Not as an actor but as director, Sean Penn shows what drives him: idealism, freedom and rebellion. His adaptation of the true story of Christopher McCandless is raw, poetic and full of zest for life. A film that feels like Penn himself: uncompromising, spiritual and full of heart.

Penn won his second Oscar for his portrayal of Harvey Milk, the first openly gay elected official in California. He plays with charm, vulnerability and conviction, without caricature. Politically relevant and emotionally disarming, lifted far above the standard biopic by Penn's empathy.

Clint Eastwood directed this heavy crime thriller about childhood trauma and loss. Penn plays Jimmy, a father who loses his daughter and is consumed by revenge. His raw, painful performance won him his first Oscar. A film that gets under your skin.

With Susan Sarandon, Penn brings one of the most powerful anti-death penalty stories ever to the screen. He plays a condemned man who slowly rediscovers his humanity. The role earned him an Oscar nomination and proved he could do more than explosive anger.

A collaboration with Terrence Malick in a war film that's anything but conventional. Penn plays First Sergeant Welsh, a man who seems cynical but is deeply affected by the absurdity of war. A film full of poetry, moral questions and gorgeous cinematography.

In Alejandro González Iñárritu's mosaic of grief and chance, Penn plays a man struggling with mortality. The film is raw and fragmented, but Penn gives it heart with acting that's as vulnerable as it is intense.

Terrence Malick's meditative masterpiece about life, loss and memory. Penn plays the adult Jack, looking back on his childhood and his brother's death. A role small in dialogue but big in feeling: Penn at his most restrained, searching and melancholic.

As slick lawyer David Kleinfeld, Penn is almost unrecognizable with curly hair and nervous energy. He faces Al Pacino in Brian De Palma's stylish crime drama, playing not the hero but the rotten core of the story, with visible enjoyment.

In David Fincher's dark psychological thriller, Penn plays Michael Douglas' younger brother. The film plays with paranoia, power and illusion, and Penn's supporting role gives the story exactly the emotional edge it needs.

A role that earned Penn both praise and criticism. He plays Sam, a man with an intellectual disability fighting for custody of his daughter. The sentiment is sometimes thick, but Penn's sincere acting and his chemistry with young Dakota Fanning make the film work.

Penn plays the feared adversary of Leonardo DiCaprio's character in Paul Thomas Anderson's widely acclaimed action drama.

Penn's breakout role as the eternal surfer-stoner Jeff Spicoli in this influential teen comedy.

Penn plays a drug dealer who, with a childhood friend, sells secret documents to the Soviet Union, based on a true story.

Penn plays an arrogant but brilliant jazz guitarist in Woody Allen's fictional biography.

Penn plays a sergeant who drags his platoon into a war crime during the Vietnam War, alongside Michael J. Fox.

Penn plays an aggressive cop who, with his experienced partner (Robert Duvall), tries to curb gang violence in Los Angeles.