Hollywood and film enthusiasts alike have had a tumultuous relationship with Sean Penn over the years. In the 80’s, he was the ultimate “Hollywood Bad Boy”: drinking like a fish and smoking like a chimney all over the press, punching his way through photographers, and marrying his way through Madonnas. That image has quelled slightly with time, though it still remains fairly well in tact.
Penn has garnered many detractors during his years in the limelight for various public and brash political statements, exhibitions of hypersensitivity and anger towards the press, and his overall “fuck you, don’t look at me because you’re not Sean Penn and I am” attitude.
No one quite knows what to make of him. Is he an ignorant, spoiled Hollywood brat who takes all his success for granted and loves to talk about things he knows nothing about, or is he a mystical artist who has walked the earth and experienced life in a way our little brains will never understand?
Whatever your opinion may be of the man (and you more than likely have one), the one unifying force that keeps us coming back to him (and keeps him employed as one of the most successful actors in the world) is that he is truly one of the most gifted, interesting, versatile, committed, emotionally vulnerable, and just downright brilliant cinematic actors of all time.
When you watch Sean Penn onscreen, you are focused entirely on his emotional believability and the immersion in his character. You fall right into his shoes and feel the movie along with him every step of the way, and you very quickly forget that he may or may not be the world’s biggest asshole in reality.
The following ten films best represent the shocking range, talent, sensitivity, and raw reality he’s brought to his work time and time again throughout the years.
10. Casualties Of War (1989)
Brian De Palma’s operatic take on the Vietnam War is a flawed and uneven mess, but it also has more moments of brilliance and power than most of the collective films released in the timespan of a month of these days. Much of this is due to Penn’s committed, horrifying, and ultimately grossly empathetic portrayal of an American soldier who leads his platoon in the kidnapping, raping, and murder of a young Vietnamese girl.
Penn is a charismatic charmer and a war hero, so we understand why the others follow him, but he’s also a sadistic bully at the turn of a dime when one member of his platoon (a very miscast Michael J. Fox) refuses to go along with his plan.
Penn plays his instrument with expert finesse, hitting every nuanced note in a seamless, fascinating performance. He is so filled with hatred towards his enemy, so overtaken by the pain the war has caused him that he truly believes his character is doing the right thing. Sean Penn makes this monstrous, horrifying reality believable, relatable, and disturbing to your core. If only the film itself entirely lived up to his performance…
9. I Am Sam (2001)
Penn’s praise (and subsequent Oscar nomination) for his work as a mentally handicapped man trying to win custody of his daughter is the subject of much scorn and ridicule. Just see Tropic Thunder.
That being said, when you view Penn’s performance and the film itself with fresh eyes, Penn is actually quite charming and heartbreaking as a man who just isn’t capable of doing most of the things “normal” people can do and take for granted every day. We see him try, we see him suffer, and we see his heart break.
Penn guides us every step of the way with an empathetic, revealing, sweet and sensitive performance. It’s a side and a color of him that is very real, very easy to forget, and very important to remember in his cannon of work.
8. The Thin Red Line (1998)
Penn gives one of his most subdued performances in Terrence Malick’s lyrical war drama. Penn’s Sergeant Edward Welsh is a stoic, emotionless, and cynical man. He pretends not to care, and makes every effort to blow off Jim Caviezel’s whimsical optimism every chance he can get.
Penn’s character has built a wall around himself, and forces himself to cease from caring about anything so he can stop feeling the loss of the war going on around him. When this wall cracks, however, the character’s (and Penn’s) enormous heart shows through just enough at the right moments (administering morphine to a dying young soldier, standing over Caviezel’s premature grave) to make for a fascinating, layered, informed, and fully realized character.
7. This Must Be The Place (2011)
Sean Penn’s answer to Edward Scissorhands and Robert Smith. His character of an aging 80’s glam rocker misfit displays vulnerability, shyness, good intentions, and just plain weirdness. His voice is unrecognizable, he moves like he’s stuck in tar, and his eyes are constantly locked in the scared innocence of a puppy dog who is looking directly in the eyes of a tornado that is about to take it off this planet forever.
Penn’s Cheyenne is a truly unique character that is unlike anything he’s ever played before… Or unlike anything just about any other actor has played before. Also, did I forget to mention that the film revolves around Penn’s journey to find a Nazi war criminal who tormented his father in WWII? Yeah, it’s that kind of movie. You just have to see it for yourself.
6. Sweet & Lowdown (1999)
If there’s an over riding theme or strength to Penn’s work as an actor, it can be boiled down to one simple word: layers. Penn’s performances are roller coasters. He is one mood one moment, and can turn on a dime the next. His characters are living, breathing, complicated, and contradictory messes of emotions.
This is exhibited wholly in Sweet & Lowdown, which happens to be Penn’s ultimate slimy little prick role (sorry Hurylyburly, Carlito’s Way, and Falcoln and the Snowman, you all came close).
Penn plays a brilliant jazz guitarist who is also a raging alcoholic and a kleptomaniac. He takes girls on dates to dumpsters so they can watch him shoot rats and impress them (or so he thinks). He also has a habit of verbally abusing his mute girlfriend on a regular basis. The character is so despicable that he is actually joyous to watch.
When his self-doubt takes over, however, and he realizes his faults and the losses he eventually suffers as a result of them, Penn’s performance takes a shattering, heart-breaking turn. What starts out as an almost a caricature-like performance turns into something very real, very ugly, and very painful. It’s the kind of turn and surprise that only Sean Penn can do.