14 Best Sean Penn Movies You Must See

There are a very few actors with the talent and charisma of Sean Penn. There are even fewer with the kind of filmography that he has. In career spanning more than three decades, Sean Penn has done a variety of roles: from a funky teenager to an aging rockstar, from a man on death row to a gay politician. He has played it all.

While some may argue that he may not be in same form as he was in the 90s or even a few years back. The counter-argument to that is his talent is still there and it will takes only one film to bring him into conversation again. In any case, it is not that Penn has vanished into oblivion. He is still there, contributing in fields other than acting. He recently directed a film starring Charlize Theron called The Last Face. He is always involved in humanitarian work. He also recently wrote a book called Bob Honey Who Do Stuff.

Till we wait for his next acting masterpiece to come out, here is the list of top Sean Penn movies. Which is your favorite?


14. This Must Be The Place (2011)

This Must Be the Place

This 2011 Indie Comedy took Sean Penn in a new Direction. Portraying a retired Rock Star (getting by off royalties) living in Ireland. ‘Cheyanne’ played by Penn, travels to the States to enact revenge upon the Nazi officer who humiliated his father during World War 2. ‘This Must Be the Place is very touching and shows you just what it is to be misunderstood and to find yourself anew even as a retiree. Penn delivers each line with courage and humility that just makes the androgynous ‘Cheyanne’ that much easier to identify with.


13. She’s So Lovely (1997)

She is so lovely

This film is more of a hidden gem for Penn fans. In ‘She’s so Lovely’ Penn portrays Psychotic Eddie Quinn, a recently released mental patient come home to reclaim his newly remarried ex-wife. What ensues is a psychological thriller of a battle (Eddie V Eddie), and a physical battle (Eddie V Joey), Joey (the new husband) played by John Travolta. This film is highly entertaining, and again Penn shows us the human behind the mental illness.


12. Fast Times at Ridgemont High (1982)


This 1982 teen comedy is a highlight of Sean Penn’s career. Sean Penn portrays slacker surfer ‘Jeff Spicoli’, delivering some of the most quotable lines of the film and of 80’s cinema. This was the first glimpse of the performance genius to come, and already Penn displayed a magnetic quality to his characterization.


11. At Close Range (1986)

Sean Penn At Close Range

Sean Penn plays a young man in a world of poverty who sees a chance at easy money, stealing farm equipments, with his estranged father, never knowing he is being drawn into a circle which includes murder. When he discovers his father’s true nature he turns informer for the government and it costs him his lady-love and very nearly his life. He goes toe to toe with no less than Christopher Walken in the film and comes out on top.


10. Sweet and Lowdown (1999)

Fast and lowdown

For Woody Allen, Penn learned to play the guitar and then gave an Oscar nominated performance in one of Allens more curious films. As a womanizing musician he is superb, though not a nice guy who routinely breaks the hearts of the women he encounters, including deaf Samantha Morton. This one happens to be one of the underrated Sean Penn movies.


9. Casualties of War (1989)


We see the disconnect when it happens, that moment when Sgt. Meserve has had enough of Vietnam and roars back in rage, committing an act of violence that is so against anything human we are stunned. Responsible for kidnapping a young Viet Cong for rape and murder, he does something repellant, and more frightening feels justified in doing it. Only few people have seen this dark brilliant drama based on a true story. A courageous performance from Sean Penn.


8. The Assassination of Richard Nixon (2004)


As Bick, a divorced little man who sees himself as so much more, Penn is remarkable, shrinking in size to portray this pathetic character. Angered and lonely after his divorce, thinking they are working things out, troubled by the corruption at his job, he decides to kill President Nixon, and actually makes the attempt before dying in a hail of bullets. Based on a true story, the comparisons to Taxi Driver (1976) were inevitable. Though Bick is not nearly as insane as Travis Bickle. Just a very sad man.

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