Sean Penn turned 52 on August 17th. I remember seeing a 26-year-old Sean Penn star opposite Madonna in Shanghai Surprise. Boy has he come a long way since then. When I think about his body of films, I am so impressed by the diversity of his choices. No role has been the same; no film the same. He makes films that he wants to make and doesn’t think about commercial appeal or critical acclaim. In fact, he’s known for wanting nothing to do with the whole Hollywood hullabaloo, yet he is one of Hollywood’s biggest guns. He’s got a reputation as a bit of a bad boy, too, thanks perhaps to his outspoken nonchalance towards mainstream Hollywood and his 36-hour stint in anger management classes for blowing up on a photographer in 2009. He’s also a devoted and active humanitarian. He’s a complex character, just like those he portrays in his movies. Perhaps that’s why he’s so compelling to watch and why his performances are always so enthralling and layered, because he brings so much of his own nuances to his roles so that they’re informed by the complexities of his own interesting persona. He transforms from the inside out and literally slips behind the veil of the characters he portrays. Here are a few of my picks for Penn’s most powerful, memorable, impactful and unexpected performances.
These two films required Penn to play vastly different characters, proof of his incredible range as an actor and his ability to transform completely into character. Penn’s portrayal of a grieved father turned monster with the best of intentions was a fine line to walk, but Penn hit it out of the ball park in Mystic River. In Milk, Penn shed the dark, tortured tones to play upbeat, openly gay politician Harvey Milk. Penn turns Milk into more than an inspirational figure. He makes him a true character with heart and substance. Not having heard much about Harvey Milk before the film, I truly felt as though I was watching a docu-style biopic thanks to Penn’s absolutely believable and uncanny portrayal of the late historical figure.
For me, the role that immediately comes to mind when I think of Penn’s filmography has got to be Fast Times at Ridgemont High. Before his dramatic roles and Oscars, a young Penn played high school burnout and California dude Jeff Spicoli. He lives in a cloud of marijuana smoke, talks like a surfer and orders pizza in class. It’s a classic movie with a great and unforgettable performance by Penn. It’s a great film to watch because it never grows tired and it serves as a wonderful reminder of Penn’s early films and the way he was able to stand out in a film while just playing a high school stoner.
I think Penn’s role in Dead Man Walking was the most impactful role of his career. I think that Penn’s performance in the film helped to establish him as the most powerful actor of his generation. He wholly becomes the character and never relinquishes, not for one single moment, his absolute and total commitment to the role. He plays a convicted killer on death row, and yes, he’s really guilty. He’s deeply flawed, tortured and without faith. He doesn’t go to his death praising Jesus. He believes in “taking things like a man,” a clichéd philosophy he lives by because he’s never developed a cultural background of any kind.
In Woody Allen’s Sweet and Lowdown, Penn delivered a brilliantly deadpan comedic performance. As the second-best jazz guitarist in the world, his musical talent somehow overcompensates for his exasperating mischievousness. When he plays jazz, all of his sins and misdeeds are forgiven. He looks like a gypsy, drinks a lot, runs a string of hookers on the side, is a bit of a doofus, lacks emotion, is vain but with an inferiority complex, yet is sweet and strangely innocent; qualities that shine through when he plays music. As only a master character actor could do, Penn embodies all of these layers to create a truly unique and memorable character.
What are your favourite Sean Penn performances? Let us know in the comments section.