Top 10 Sean Penn Performances

This Academy Award winning actor has starred in countless memorable roles. Showcasing his skill in front of the camera, he has given a wide range of gripping performances, playing everything from teen stoner, to crooked lawyer, to mentally handicapped father and even a convicted killer. Join as we count down our top 10 favorite Sean Penn performances.

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Top 10 Sean Penn Performances

He’s been everything from a teenage stoner to stone-cold killer! Welcome to, and today we’ll be counting down our top 10 favorite Sean Penn performances.

#10 – Cheyenne: “This Must Be the Place” (2011)

Kicking off our list is Penn’s mesmerizing role as a retired Goth rock star. Bored of living off royalties, he journeys to America and tries to realize his dead father’s unfulfilled desire to kill the Nazi war criminal who tortured him. Penn owns the role by completely transforming into the soft-spoken, straight-faced and jaded rocker who slowly rediscovers himself, while also finding a new sense of maturity.

#9 – Eddie Quinn: “She’s So Lovely” (1997)

In this tear-jerking drama about the dark side of love, Penn stars opposite his real-life wife at the time, Robin Wright. Playing an irrational psychotic with violent tendencies, he ends up in a mental institution and loses his wife to another man. Penn uses this set-up to give us a depressingly bleak and convincing portrayal of the descent into madness.

#8 – Paul Rivers: “21 Grams” (2003)

Playing a college professor with a terminal heart problem, Penn takes his place at the center of this non-linear story. He hooks up with the widow of a deceased heart donor following a tragic car crash, and soon agrees to help her exact her revenge. This premise allows Penn to deliver a powerful, conflicted, yet reserved performance that helps the story unfold brilliantly.

#7 – David Kleinfeld: “Carlito’s Way” (1993)

It’s hard to recognize him, isn’t it? In a role that’s unlike any of his others, Penn morphs into Al Pacino’s sleazy, curly haired lawyer, and earned a Golden Globe nomination for his work. His character is an immoral gangster wannabe who’s more than a little addicted to cocaine and is in way over his head, but it also shows his emotional breakdown in the face of underworld cross-dealings and betrayals, making him a complex character.

#6 – Emmett Ray: “Sweet and Lowdown” (1999)

This Woody Allen comedy sees Penn take on the fictional role of a gifted 1930s jazz guitarist who ruins his one chance at true love. Penn uses the larger-than-life part to play up the deadpan comedy, but it was his transformation into the vein, crude and egotistical womanizer that wooed critics and earned him a Best Actor Oscar nomination.

#5 – Matthew Poncelet: “Dead Man Walking” (1995)

This is another Academy Award-nominated performance. Penn plays a man who’s comforted by a nun while on death row for the rape and murder of two teens. To portray this complicated character, Penn doesn’t just put on an accent and goatee: he uses each scene to humanize his flawed persona by adding relatable idiosyncrasies and by showcasing a mounting fear of death. His impressive performance fills us with empathy, despite his horrific past.

#4 – Sam Dawson: “I Am Sam” (2001)

In this Oscar-nominated tour-de-force; Penn plays a developmentally disabled man who is raising his daughter with the help of his other disabled friends. However, he ends up in a legal battle when the state removes her from his custody. A believable and bittersweet role, it allows Penn to tug at our heartstrings, raise moral issues, and demonstrate that a person’s heart can trump their other limitations.

#3 – Jimmy Markum: “Mystic River” (2003)

Penn won both a Golden Globe and an Academy Award for his tumultuous performance as a devastated man who’s unable to deal with the brutal slaying of his daughter. As the movie is centered on that character’s search for vengeance, the narrative owes much of its success to Penn’s ability to leave us breathless and move us to tears – especially when he lets out his haunting cries…

#2 – Jeff Spicoli: “Fast Times at Ridgemont High” (1982)

This role may not have won Penn any love with the Academy, but it remains one of his most legendary performances. Penn functions as the movie’s greatest source of comic relief as the jobless surfer. He regularly brings the laughs by clashing with his teacher Mr. Hand, by spouting outrageous one-liners, and by sharing his own bizarre brand of uninspired wisdom.

#1 – Harvey Milk: “Milk” (2008)

Taking the top spot on our list is Penn’s cheerfully optimistic Oscar-winning portrayal of America’s first openly gay elected official. An inspiring, captivating and passionate depiction, Penn expertly helps us get to know the once-closeted Republican, and shows us his courage in the face of the prejudice and hatred that ultimately cost him his life.

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