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Happy Birthday Sean Penn: Some of the actor-director’s finest works worth watching
Shilpa S
Aug 17, 2021
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To say that Sean Penn has made waves in Hollywood would be an understatement. In his stunning career over four decades on the silver screen, Penn has essayed different roles across genres, making him one of the finest actors in Hollywood. But not one to limit himself, he has also donned the role of a director, screenwriter and producer, replicating his success on screen while behind the camera as well.

As the Academy Award-winning Hollywood heavyweight turns 61, let’s take a look back at some of the highlights of his career

1
Mystic River
8.3OTTplay Rating
Directed by the legendary Clint Eastwood, Mystic River is based on a novel of the same name. It tells the story of three men, former childhood friends, who drift apart over the years, but cross paths once again when one of their daughters is killed. Sean Penn’s gut-wrenching performance as a grieving father out to settle scores with the man responsible for his irrevocable loss is haunting. He won the Academy Award for Best Actor for his role.
2
Dead Man Walking
8OTTplay Rating
Inspired by a non-fiction book of the same name, Dead Man Walking narrates the story of a Roman Catholic nun who develops a bond with a death row convict played by Sean Penn. It is never easy to essay the role of a real person, let alone someone as vile as a real-life murderer and rapist, but Penn manages to portray the character in a way that makes the viewer feel sorry for the remorseful criminal. His dynamic with co-star Susan Sarandon also earned him accolades.
3
I Am Sam
8.1OTTplay Rating
I am Sam is a touching tale of an intellectually disabled single father Sam who struggles to gain custody of his young daughter. Although Sam’s life is hard, he has support from his friends. The film earned negative reviews but Sean Penn’s performance as the disabled man who strives against all odds for his child was commended. His portrayal of the character, in a sensitive way, is what makes the film worth watching.
4
Into the Wild
8.5OTTplay Rating
Featuring Sean Penn in the director’s chair, Into the Wild is the story of a young man who, after becoming disillusioned with the way of the world, decides to hike across the wilderness, living off the land. It is based on the true story of hiker Christopher McCandless. Penn’s assertive directional style leads to a poignant rendition of the real-life story, one that is worthy of the praise and acclaim it received. He was lauded for managing to convert the true story into a movie that left its audience spellbound.
5
Carlito's Way
8.2OTTplay Rating
This crime drama is based on a series of novels by Judge Edwin Torres, a former Supreme Court judge in the US. Set in 1975, Carlito’s Way tells the story of a convicted criminal who, upon being released from prison, vows to lead a life free of crime. But it is easier said than done. Sean Penn gives a compelling performance in the role of the criminal’s close friend and lawyer who tries to free his friend from prison. His performance as the hot-headed lawyer, revealed to be as sketchy as his friend, is definitely something that stands out in the film.
6
Fair Game
7.1OTTplay Rating
Based on real events, this political drama tells the story of an agent of the Central Intelligence Agency, whose identity is kept a secret from everyone outside the agency except her husband and parents. When her diplomat husband writes an article against the reigning government, her cover gets leaked to the media, by the possible hands of the administration itself. Sean Penn’s performance as the husband, lacking the understanding and empathy to be there for his wife, gained critics’ approval and left fans seething.

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