The 10 Best Sean Penn Movies You Need To Watch

5. At Close Range (1986)

At Close Range

This is the role the put Sean Penn on the map as a serious, brilliant actor in his early career in the 80’s. The film and the performance started comparisons to Brando, DeNiro, James Dean, and just about every other iconic great actor of past generations. It was the expert precision of how Penn handled the arc of his character that put him in the category of the greats before him.

Penn starts off as a naïve, small town kid. Maybe a little bit of a hellraiser, but overall a good kid. He meets a pretty girl, falls in love, and wants to start a life with her. It’s the American Dream, young love, and whimsy captured beautifully complete with an 80’s score (which is pretty much a single riff on a Madonna song that accompanies the movie played over and over again).

Penn is the beautiful, troubled kid with a heart of gold, and he captured the “Little Boy Lost” act with perfection that nobody had nailed since James Dean thirty years earlier.

Then the movie shifts, and so goes Penn’s performance with it. Penn’s criminal father shows up (played with great sleaze by Christopher Walken), sucks Penn into his world, uses him up, and everything goes to hell. Depth is all over Penn’s performance as the movie progresses. In a scene in which his father publicly humiliates him, Penn is able to exhibit a kind of pain everyone can relate to without saying a single word.

When Penn finally stands up to his father and tells him he’s done dealing with him, you see so much thought and growth behind his eyes, it’s almost magical.

The defining moment of At Close Range, however, is the explosive set piece of the entire film. It is the scene that officially made Sean Penn a bona fide actor and movie star: after being left for dead at his father’s hand, Penn returns to this father’s home. Both actors play it cool until the scene becomes what it has to be: an utter eruption of emotion, pain, and confrontation.

Penn exhibits the kind of intensity and commitment Brando showcased in A Streetcar Named Desire, and delivers one of the most emotionally volatile scenes ever accomplished by an actor under thirty (Penn was shockingly only twenty four when he filmed this movie). Penn screams, cries, jams a gun in his father’s face, then comes to peace with himself in a matter of two minutes of screen time.

It’s amazing ride, and of course credit is also due to director James Foley and editor Howard Smith for it’s smoothness. It is Penn’s emotional commitment to the scene, however, and the depths of which he shows us that cannot be faked or indicated which make it so captivating and painful to watch. It is a scene, as much as any other, that epitomizes the true strengths of Sean Penn’s acting career.


4. Fast Times at Ridgemont High (1982)

Fast Times at Ridgemont High (1982)

Penn’s comparisons to Dean, Brando, and De Niro are always going to follow him, but he will always have one major attribute over every singe one of them: Sean Penn has the ability to be a comedic genius if he truly wanted to be.

Given his career choices over that last few decades, it’s pretty safe to say that’s not high on his list of ambitions, but we can never forget that, once upon a time when Sean Penn was an up and coming actor, he played one of the most iconic comedic roles ever put on film: Jeff Spiccoli.

Much like Steve Martin in The Jerk, Bill Murray in Ghostbusters, or John Belushi in Animal House, Penn owns his iconic screen comedic idol. He throws the same obsessive commitment into playing this doofish stoner as he does in playing a war veteran.

When he pounds his head with his shoe after taking a huge hit out of a bong, then exclaims to his friend on the phone, “That’s my skull!”, Sean Penn proves he is an actor capable of pulling off anything. Literally anything.


3. Milk (2008)


For all the attention and awards this performance mustered (and rightfully so), it should be stated that Sean Penn’s portrayal of Harvey Milk is, in many ways, the quietest, most introspective, and subtle performance he’s ever given. That’s not exactly the type of roles the powers that be give so much praise towards around awards season, so good for them that time around.

What makes Penn’s performance spectacular is that it’s so seamless it’s almost invisible. Penn lives and breathes Milk’s compassion, empathy, and humanity with so much ease you truly forget you’re watching an Oscar-winning actor’s performance.

You love this man, you feel how much he cares for what he’s fighting for, you believe every word he says and every step he takes, and your heart breaks when he is ultimately punished for his attributions to the world. Penn achieves these emotions because he’s not simply acting them, he’s living them on camera.


2. Mystic River (2003)

Mystic River (2003)

Sean Penn’s performance as a grieving father who will do just about anything to solve the murder of his teenage daughter is a performance that, quite simply, has Sean Penn doing what Sean Penn does: he owns the screen, he owns the movie, and he, of course, owns the character.

Penn’s character is essentially Boston’s hidden godfather. The lines on Penn’s face, the violence in his eyes, and the stories behind his gaze make him an intimidating and believable choice for the character. He has a past, he has a present, and you can somehow feel it all without him saying a word. This is one of many gifts Penn has as an actor: every character he plays somehow feels lived in.

The gravity of his character’s personality and presence feed into the next step of it’s bravado when Penn’s strong, brutish, and intimidating force is overtaken with grief by the loss of his daughter. When the two sides of the character (the grieving father and the hidden gangster) finally connect, the audience gets to see Penn pull off one of the most successful and complicated roles of his career: a man who is equally dangerous and sympathetic.

Penn’s role in Mystic River is a breathtakingly bold, painful, and skillfully empathizing orchestration of loss and pain. A major underlying theme in both his work in general and his character in Mystic River is just that: pain. And Sean Penn goes through so much hell so the he not only makes you think it’s real for him, he makes it feel real for us, too.


1. Dead Man Walking (1995)


If there is a singular defining work for any actor, it is usually one that somehow culminates and showcases all their strengths and abilities into one role. Very few actors get the opportunity to play such a role, and, when they do, very few of them are able to entirely pull it off.

Brando in A Streetcar Named Desire, DeNiro in Taxi Driver, James Dean in Rebel Without A Cause, Heath Ledger in Brokeback Mountain… Those actors own those roles, those actors perfected those roles, those actors are their roles.

Sean Penn’s work in Dead Man Walking not only belongs in that pantheon, it quite possibly tops it. Penn has the ultimate challenge of an actor in this role. He plays a death row inmate nearing the final days of his life. Everyone knows he’s guilty of rape and murder, yet he keeps fighting for his innocence and refusing the help of a nun (Susan Sarandon) trying to get him to repent for his crimes.

Once again, Penn’s performance is a roller coaster of emotions. He’s belligerent, violent, and sleazy, then he’s childlike, endearing, and even funny. As the film progresses, he showcases fear, guilt, and ultimately unbearable agony over having to face the reality of what he’s done. We hate him as much as he hates himself, and we eventually feel sorry for him as much as he does so for himself.

As per usual, as an audience to Penn’s work, we don’t just sit back and watch him go through his actions. Penn’s power as an actor and as a human being is that he makes you feel all of it, too. Every agonizing second of it.

Sean Penn’s work in Dead Man Walking transcends performance. It is a complete immersion into character, into emotion, and into the suffering of consequence. Penn wasn’t only robbed of an Oscar for this masterwork, he was robbed of a Pulitzer Prize. His work is that important in this film.

It is as much of a brutal, honest, and empathetic screen performance as any actor has ever given. And there is no other actor who could have pulled it off the same way. I don’t know who Sean Penn is, I don’t know where he came from, but I am forever glad he is here doing the work he is doing. Seriously, who gave this son of a bitch his green card?

Author Bio: Matt Hendricks is an independent filmmaker with several projects currently in development.