Top 5 Sean Penn Films

In celebration of Sean Penn’s 54th birthday this month, here’s a look back at his greatest films.

Sean Penn cemented himself as a household name very early on in his career in the 1980s, however, this was more on account of his marriage to Madonna, rather than this acting ability. Some of his early films include Taps (1981) and Fast Times At Ridgemont High (1982), but he did not reach critical acclaim until the late nineties when he received his first academy award nomination for his role in Dead Man Walking (1996). The next decade saw Penn land multiple powerful roles that earned him further nominations as well as fame in his own right, separate to his now ex wife. Unlike other actors around his vintage,  such as Robert De Niro and Sylvester Stallone, he has never really been typecast, and he continues to bring all sorts of colourful characters to life. He has certainly had an eclectic career with performances in a variety of genres, and involvement in projects of varying success. He started to try his hand at directing in the 1990s, but never really received much recognition in this area until his 2007 film Into The Wild. Some of his more recent works, such as Gangster Squad (2013) have been a little disappointing, but hopefully he will redeem himself in The Gunman, in which he stars opposite Javier Bardem, Idris Elba and Ray Winstone. The Gunman is due to hit cinemas early next year.


Top 5 films in chronological order:
1. 2001. I Am Sam.
Directed by Jessie Nelson.
Starring Sean Penn, Dakota Fanning and Michelle Pfeiffer


It’s an obvious choice, but nevertheless I Am Sam certainly deserves to be in the top 5. Penn plays Sam Dawson, a man with a mental disability that has left him incapable of developing intelligence any higher than that of the average seven year old. When a homeless woman gives birth to his child, and abandons both him and their newly born daughter, Sam is forced to look after this baby as a single parent. So named Lucy after a Beatles’ song, Sam’s daughter (Dakota Fanning) struggles to grow up under his care, particularly when her mental capacity begins to outgrow his own. Eventually protective services become aware of the situation and step in, separating father and daughter. Cold and callous lawyer Rita Harrison (Michelle Pfeiffer) agrees to take on Sam’s case, at first only to prove to others that she is not completely heartless, but as she becomes further acquainted with Sam she becomes genuinely motivated to help him. Jessie Nelson’s direction is beautiful in the way she presents the world of the film through Sam’s perspective. Not only is the story incredibly moving, but the performances from both Penn and Fanning are also astonishingly good.

2. 2003. Mystic River
Directed by Clint Eastwood
Starring Sean Penn, Kevin Bacon, Tim Robbins, Laurence Fishburne and Marcia Gay Harden


Chilling from start to finish, Mystic River explores how one tiny twist of fate can completely alter the course of a person’s life. The film opens in a neighbourhood street in Brooklyn in 1975 where three young boys are causing mischief, when a man claiming to be a police officer threatens to discipline them. Under the pretext of taking him home to his mother, the man convinces one of the boys to enter his car. For four days the boy is locked up and abused, and although he manages to escape, he is forever altered by this horrifying experience. This boy, Dave Boyle (Tim Robbins) grows up to be a husband and a father estranged from his boyhood friends; Jimmy Markum (Sean Penn), who is now an ex con and general store owner, and Sean Devine (Kevin Bacon) who has gone on to be a police officer. The three of them still live in the same town in Boston, and whilst tragedy drew them apart as kids, it brings them together again all these years later, when someone close to them is mysteriously murdered.

3. 2003. 21 grams
Directed by Alejandro Gonzalez Inarritu
Starring Sean Penn, Naomi watts and Benecio Del Toro

21 GRAMS.png

In 21 Grams, screenwriter Guillermo Arriaga employs a truly innovative style of storytelling in which he presents the interconnected lives of 3 characters in non-linear fragments, hence leaving the viewer to piece the puzzle together, and independently learn how these characters became involved with one another. Sean Penn plays Paul Rivers, a mathematician with a fatal heart condition that has caused his health to significantly deteriorate. Through a series of unexpected events, his world becomes intertwined with married mother of two, Cristina Peck (Naomi Watts), as a result of the actions of Jack Jordan (Benecio Del Toro), an ex con turned born again Christian. The performances from all three of the main actors are outstanding, as is the shadowy and grainy handheld cinematography.

Special Mention:
The Assassination of Richard Nixon (2004)
Sean Penn also shares the screen with Naomi Watts in The Assassination of Richard Nixon, which contrary to its title, is not actually a political thriller. Don Cheadle and Jack Thompson also feature in this poignant film about how the little people are top often downtrodden by the wealthy and powerful in America. Penn delivers a performance that will resonate with you long after the film has ended, but the film as a whole is not quite as strong as 21 Grams.

4. 2008. Milk.
Directed by Gus Van Sant
Starring Sean Penn, James Franco, Josh Brolin and Emile Hirsch


Many were surprised when Sean Penn took home the Oscar for his portrayal of homosexual politician Harvey Milk over that of Mickey Rourke for his role in The Wrestler, but nevertheless, Penn delivers once again in this biographical drama. In the 1970s Harvey Milk was a gay activist, who later became California’s first openly gay elected official. The film follows his struggles to stand up for gay rights during such a homophobic time period as well as his relationships with his followers and partners. This film will resonate with you long after it has ended, and will leave you horrified by how society behaved only a few short decades ago. Whilst a lot has changed since then, we certainly still have a long way to go.
5. 2011. This Must Be The Place.
Directed by Paolo Sorrentino
Starring Sean Penn and Frances McDormand


Quirky and fabulous, This Must Be The Place revolves around retired rock star Cheyenne (Sean Penn) who is living his days out in Dublin, when he learns that his father, with whom he has been estranged for many years, is close to death. Cheyenne takes off to New York to reconcile with his father, but unfortunately he is too late. His trip is far from fruitless, however, as he learns how his father was mistreated by a particular SS Officer during his time at a camp in Auschwitz. Before returning home, Cheyenne makes it his mission to track down this officer, and find justice for his father. Penn is eerily convincing as Cheyenne, who is this bizarre blend of femininity and punk rock, and has a very interesting way of perceiving the world around him. He also has a knack for making profound, yet humorous statements, and the film as a whole is both an oddity and a hilarity that is most definitely worth watching.


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