5 Roles That Prove Sean Penn Is Either A Great Actor, Or The Greatest Actor

This Must Be The Place 5 Roles That Prove Sean Penn Is Either A Great Actor, Or The Greatest Actor

Sean Penn is a serious man. Every now and again we’ll get a glimpse of how serious he can be even in the midst of comedic settings, like that year at the Oscars when he condescendingly mansplained to host Chris Rock who Jude Law is. His seriousness can make him hard to be publicly at times. But it’s also likely the primary contributing factor to just how devastatingly good he is at acting.

He was first introduced to a large audience in the 1982 comedy Fast Times at Ridgemont High as the iconic character Spicoli, but since then he has evolved into an actor who can play a variety of characters ranging from stoned surfer to hardened death row inmate. He’s also shown a propensity for picking interesting projects to be a part of, a sign of an actor who’s as sharp as he is talented. His contributions to movies of Terence Malick is particularly admirable, even if he isn’t always happy with the end results. More recently, he’s shown his talent behind the camera, directing the critically beloved Into the Wild. Unlike Ben Affleck though, he’s too good of an actor for anyone hopes he gives that up in favor of directing.

There are 5 pivotal roles that transformed Sean Penn from solid supporting actor to one of the most reliable and electric leads of his generation. It’s interesting to see how he’s progressed as an actor, seeming to improve with each performance, right up to his best work in his most recent Oscar-recognized film.

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1) Dead Man Walking

Dead Man Walking 5 Roles That Prove Sean Penn Is Either A Great Actor, Or The Greatest Actor

He had some notable roles here and there, and he had a bit of a bad boy image in the public eye, but in 1995’s Dead Man Walking, Sean Penn finally got to show a serious amount of depth. He starts out early in the movie fairly subdued, acting tough and guarded. We’re used to seeing a fair amount of expression in his eyes, but here he’s got them lowered at all times, eyebrows in a perma-scowl and lip sneering without remorse. It’s a hardened exterior that Penn pulls out so magnificently that the transformation and eventual redemption of his character is that much more effective; we have to believe that he’s someone who has truly changed his ways, and so a contrast is essential between the Matthew Poncelet we meet at the beginning of the film and the one we see at the end.

By the film’s end, in the scene leading up to Poncelet’s execution, we see this change coming to fruition before our eyes. Penn’s eyes at this point have cast away all defenses and he’s fully engage with the Susan Sarandon character, accepting the philosophy she’s instilled in him and finally reaching out to the parents of his victims just moments before he’s lethally injected. It’s a big acting moment but Penn doesn’t take it too far. He keeps it real, restrained, refrains from speechifying too much, and delivers a final scene that brings the movie together emotionally in the end.

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2) Sweet and Lowdown

Sweet and Lowdown1 5 Roles That Prove Sean Penn Is Either A Great Actor, Or The Greatest Actor

If it was just a move to show off his range, Sean Penn’s turn as jazz guitarist Emmet Ray in Woody Allen’s Sweet and Lowdown would have been a resounding success, but of course reducing it to a simple career move would be cynical. At this point in his career, post-Dead Man Walking, Penn did not veer into comedic territory very often, which is a shame because in Sweet and Lowdown we see what incredible comedic effect a typically serious actor can have when they play an oddball character completely straight. It’s mesmerizing. So Penn’s role as the second greatest jazz guitar player of all time is a funny premise, but the fact that he makes everything about him mildly believable, right down to the trance he appears to go into when he’s making music, makes it a spectacular performance.

It’s hard to not talk about Samantha Morton in this movie because for pretty much every scene she’s in, we can’t take our eyes off of her. Much of this is because she doesn’t speak, and so every gesture is heightened and our attention is more focused. Silence has a way of doing that. But balancing this out is Penn’s logorrheic performance that is occasionally interrupted when he speaks with his guitar. If his Matthew Poncelet face was grave and mean, his Emmet Ray face is tense and energetic and eccentric. It’s hard to imagine that the same guy is playing both these parts.

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3) I Am Sam

I Am Sam 5 Roles That Prove Sean Penn Is Either A Great Actor, Or The Greatest Actor

So at this point we’ve seen, among a bunch of other roles, Penn goes from a violent racist dude to an eccentric and ambitious musician, and now, to a developmentally delayed father fighting to retain custody of his daughter. My own memory of the first time I watched this movie is hazy; I think I was far less discerning at the time. Penn’s performance in it, however, is hard to deny. Unlike Roger Ebert, I don’t think playing a role this involving is that much easier on an actor—although I’d leave it to the actor to have the final say on the issue. There’s more going on in Penn’s manner here than his labored speech, movements and facial expressions. It’s that element that makes the performance every bit as good as Penn is in Sweet and Lowdown, that even when you concentrate really closely on his acting, it’s incredibly hard to find much of Sean Penn as we know him in this character. The quality of the movie notwithstanding, when people wonder what folks mean when they speak about an actor disappearing into a role, I Am Sam is a film they could be directed to.

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4) Mystic River

Mystic River1 5 Roles That Prove Sean Penn Is Either A Great Actor, Or The Greatest Actor

In 2003 Sean Penn reunited with Dead Man Walking director Tim Robbins, who is in front of the camera this time, in a role similar to his death row killer character in terms of toughness, and perhaps could be the same guy if he existed in an alternate timeline where he had a daughter and reformed himself to a degree. Penn adapts his performance appropriately: in addition to taking on the proper Massachusetts accent, he once again dons the kind of vulnerability-masking hardness that we saw him put on as Matthew Poncelet. In Mystic River, he’s shown how much he has matured as an actor, giving perhaps the most nuanced performance of his career at the time. He’s feeling so many mixed emotions throughout the film, mournful sadness and vengeful anger, powerlessness and an obsessive desire for retribution. Often we see him express these emotions all at the same time. It’s a testament to the character’s inability to process emotions he’s never been exposed to in his complicated life. The one scene where we see him at his rawest is especially powerful and heartwrenching, and it’s important to keep those raw emotions in mind as we witness his actions throughout the movie. It’s such a rich performance, and even more so for its time. It’s hard to believe this was a movie released ten years ago until you rewatch it.

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5) Milk

Milk 5 Roles That Prove Sean Penn Is Either A Great Actor, Or The Greatest Actor

There’s this perception that if an actor portrays a real life figure that they’re pretty much guaranteed to garner awards so long as they don’t screw it up royally. I think it’s becoming more and more apparent that this is not necessarily the case. There have been so many instances of actors nailing real historical people who exist in the realm of audio and video archives that it’s not much of a novelty anymore; actors need to bring something extra, tap into a certain truth or depth of a character, making them movie real in addition to reality real. That is, fleshing them out so that they seem real as opposed to leaving them as two-dimensional news footage figures.

This is why Sean Penn won over critics and audiences alike for his work in Milk. The assumption from everyone who had seen The Wrestler was that Mickey Rourke had given the performance of the year in that movie by Darren Aronofsky. And then Milk came out, and Sean Penn gave the performance of his career. We see him again completely become Harvey Milk, and transform every detail of his movement to that of this unique figure. He dictates the emotion of each scene with power and grace, from the intimate moments to the massive speeches. The fact that he was playing such a heroic figure helped, but Penn was able to capture someone who had many dimensions, some less admirable than others, and still harness precisely what made him such a transformative figure all the same.

This is but a sample of Sean Penn’s work—probably the cream of the crop, granted, but he has so many smaller roles that he’s made more out of than perhaps was expected of them. There’s a certain element of risk to each role he takes on as well that tends to be particularly thrilling. They could very easily go bad, but very few of them do. Among his generation of actors, there can’t be any doubt that he belongs at the top end of the list, can there? As far as I’m concerned, he can be as serious as he damn well pleases.

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  • RushLimbaughsFatAss

    Great article. Sean Penn is a great actor. However, I think that I would swap either the character he played in Falcon and the Snowman or Casualties of War in place of I Am Sam, that’s probably my least favorite role of his.