(Credit: Sachyn Mital)

From Brian De Palma to Clint Eastwood: The 10 Greatest Sean Penn Film Performances

So if we have anything original to offer, it’s to speak from our own life about the society we’re in.
– Sean Penn

American actor, producer and director Sean Penn has established himself as one of the best actors with critically acclaimed performances in films like Mystic River and Milk among others. He has two Academy Awards to his name and several nominations. Apart from his brilliant film career, Penn has been engaged in political social activism, including humanitarian work in the aftermath of Hurricane Katrina in 2005 and the 2010 Haiti earthquake.

Penn acting career started with humble beginnings with a cameo in Little House On The Prairie. He soon garnered critical success for his performance in At Close Range (1986), before quitting acting for a few years after growing disillusioned with the industry. He then returned emphatically with an Academy Award-nominated performance in Dead Man Walking (1995).

On his 60th birthday, we take a look at some of the best performances in Penn’s illustrious career.

The 10 Greatest Sean Penn Film Performances:

10. The Falcon And The Snowman (John Schlesinger – 1985)

John Schlesinger’s “truth is stranger than fiction” thriller is based on a very real and bizarre story about a disillusioned defence contractor (played by Timothy Hutton) and his coke dealer friend (played by Sean Penn) who become spies for the Soviet Union at the height of the Cold War. Penn puts in a compelling performance as Andrew Daulton Lee, a drifter whose life has taken a strange turn.

Speaking about the subject matter, Schlesinger once said, “I think when you are dealing with real people, the one concern you have is you have a responsibility to them to play fair. So you’re more concerned with accuracy and how something could have happened but at the same time you’re dealing with a film, so you have got to feel free to condense time, amalgamate characters and take some liberties.


9. Carlito’s Way (Brian De Palma – 1993)

Often viewed as the spiritual sequel to Scarface, this 1993 crime drama stars Al Pacino as a Puerto Rican ex-con who vows to turn his life around after getting out of jail. However, his lawyer (played by Penn) pulls him back into the dark underworld of drugs and crime. Sean Penn earned a Golden Globe nomination for Best Supporting Actor, thanks to his wonderful and almost unrecognisable portrayal of the role.

Carlito’s Way was again, treated like another Al Pacino gangster movie kind of business. But it was really a great script, based on two novels written by Edwin Torres. Again, at the time it came out, not much attention was paid to it, though I thought it was a very skillfully made movie from a very good script,” said director Brian De Palma.


8. The Thin Red Line (Terrence Malick – 1998)

Terrence Malick’s World War II epic boasts a star-studded cast which features Penn alongside the likes of Adrien Brody, Jim Caviezel, Ben Chaplin, George Clooney, John Cusack and Woody Harrelson. Penn is brilliant as 1st Sgt. Welsh, a cynical soldier who doesn’t believe in the war he is fighting in. Pvt. Bell (played by Jim Caviezel) is the perfect antithetical element as an optimistic soldier in Malick’s philosophical work.

“It took me a little bit of time to adjust to it, it took me a couple of weeks and some heart to heart conversations with Terry (Malick) about what contribution I could make because I had never been involved in something [so big],” Penn recalled.

“There was a time where I was having a bit of a crisis with [the picture and my role] where I felt that my understanding of it was that it was getting a little too black and white for me. I explained this with a lot of energy and emotion to Terry and his answer — after I’d been up all night worrying about this two weeks into shooting – he just said, ‘Oh, I think we’re just fine’,” he added.


7. 21 Grams (Alejandro González Iñárritu – 2003)

Sean Penn plays the role of Paul Rivers, a critically ill maths professor in desperate need of a heart transplant in Iñárritu’s wonderful film, which investigates how one accident can impact so many different people. The director uses non-linear narrative styles to highlight how our lives intersect. Penn ended up receiving a BAFTA nomination for Best Actor for his portrayal of Rivers.

Iñárritu explained the sentiment behind his masterpiece, “For me, basically it’s a film about loss and about hope. How we can find hope experiencing such extraordinary losses, how we can survive that. That’s what I love about these characters, about their weaknesses and strengths. And in the end, it’s a love story. Watching Naomi and Sean, I was really moved by the raw circumstances, and how these lonely people need each other.”


6. At Close Range (James Foley – 1986)

Based upon the true story of Bruce Johnston Sr., his son, and his brothers, Foley’s gritty crime thriller presents a dysfunctional family who is also one of suburban Philadelphia’s most notorious crime families during the 1970s. Their crimes start off petty with burglaries before escalating to murder as they get lured in deeper into the murky world of crime.

One of Penn’s best early roles, he plays the character of Brad Whitewood Jr. whose role model is his father, a supreme criminal. Foley launches a moving investigation of how important the role of a father is as well as how disastrous things can get if he is negligent and reckless.


5. Sweet and Lowdown (Woody Allen – 1999)

Set in the 1930s, Allen’s film sees Penn play jazz guitarist Emmett Ray who idolises the famous musician Django Reinhardt. Ray falls in love with a mute girl (played by Samantha Morton) who is a continuous source of support for him despite his run-ins with the mob and adultery with Uma Thurman’s character. Both Penn and Morton were nominated at the Oscars in Best Actor and Best Supporting Actress, respectively.

Woody Allen praised Penn’s performance, saying, “You hire someone like Sean. He’s been great for years before I met him. The thing that you want is not to mess him up. I want him to do that thing that Sean Penn does that he’s always been great at. So I hardly had to do anything at all with him. People think that I’m joking when I say that 90% of my direction is either ‘Faster!’ or ‘Louder.’ They think that I’m joking but I’m not joking.”


4. Fast Times At Ridgemont High (Amy Heckerling – 1982)

This is the film that was Penn’s breakout moment as a movie star. He plays the role of Jeff Spicoli, a stoner who only indulges in surfing and women. The high school comedy conducts honest discussions about sexuality and personal identities, despite the light subject matter. Penn is memorable as Spicoli, putting on an on-screen persona much like The Dude in The Big Lebowski.

Director Amy Heckerling spoke about the film’s authentic nature, “I read the script and it was wonderful, but it had a lot of studio-ish-ness in it. I found out it was based on other material and I asked to read [Cameron Crowe’s] book. The book is amazing. Every single thing, you go “Yeah, yeah, yeah,” because they’re all real.

“I liked that aspect of young people having to deal with a world that’s not going to be as good. Their dreams are being squashed down a bit,” she added.


3. Dead Man Walking (Tim Robbins – 1995)

Tim Robbins’ 1995 crime drama is a searing work which explores the morality of capital punishment and insists that murder cannot be solved with murder. The film stars Sean Penn as a death row inmate Matthew Poncelet who forms a special bond with a nun (played by Susan Sarandon). Sarandon won the Oscar as Best Actress, while Penn finally got his first Best Actor nomination.

“Sean Penn was my first choice, and I think he’s the best actor of his generation, and I just wanted to go to the best first. And I had heard he had stopped acting, but he responded immediately to the script and said yes right away,” Robbins declared.

“He said that when he read it, he, he cried, and he, he just felt that it was a, a good script, and he wanted to do it,” he added.


2. Mystic River (Clint Eastwood – 2003)

Based on a novel by Dennis Lehane, Eastwood’s haunting film investigates how childhood trauma causes irreparable damage to the adult psyche with Penn on brilliant form as former convict, Jimmy Marcus. He and his friends were subjected to child abuse when they were young and those wounds never really healed. For his powerful performance, Penn won his first Academy Award for Best Actor.

While speaking about his motivation to make the film, Eastwood said, “It’s very difficult to say what attracts you to the project, but I’ve always been very curious about victims of crime, victims of child abuse, one of the most hideous crimes we have on the planet. There’s a certain father’s nightmare in the drama of this film, how one [terrible] tiny incident affects so many people.

“It’s a kind of fate-driven story, a train you can’t get off, like it or not. Kevin has a speech at the end of the movie: ‘Maybe we all got in that car that day.’ It’s baggage these characters carry from when they are little boys.”


1. Milk (Gus Van Sant – 2008)

Penn’s portrayal of Harvey Milk, California’s first openly gay elected official, sees him deliver the best performance of his career. The biographical drama presents the flawed society we live in and the prejudices that are omnipresent. Penn won his second Academy Award for Best Actor, his performance is a wonderful tribute to the pioneering LGBTQ rights activist.

“I was graduating high school the year Harvey Milk was killed, so I was in California, and I was certainly aware of it — it was national news, anyway,” Penn recalled. “I didn’t know anything more than this openly gay politician was murdered alongside the mayor of San Francisco. I think it was only a month after the Peoples Temple [Jonestown mass murder] thing had happened, which was mostly San Francisco people, so it was kind of a crazy moment in Northern California.”

“The main problem was that normally, to tell a whole life in two hours, you want to get somebody more charismatic than the real person. And in this case, one could only aspire to that,” he added.

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