Sean Penn is one of, if not the best, actor of his generation. He might be a grumpy, outdated "homophobe" (according to Mickey Rourke) and "fool" (according to Thandiwe Newton), but there's no denying that he's a great actor, one of the best to completely inhabit their roles until they become their character (who knows, maybe Penn is preparing to play a transphobic person?).
How else do you explain how Penn so deftly played stoner Jeff Spicoli in Fast Times at Ridgemont High, Jimmy Markum in Mystic River, and Harvey Milk in Milk? In each of those three roles, Penn’s performances were pure art, and yet they couldn't be more different. All of his roles are a master class in what it takes to be a truly exceptional and remarkable actor.
Many actors tend to gravitate to the same type of character movie after movie, few of them having the range of talent and ambition to take on wildly different characters time and time again. Penn’s acting career started with an episode of Little House on the Prairie in 1974. He was actually an extra for an episode that his father Leo directed. His first film role was in 1981’s Taps, in which he played a cadet at a military high school. His very next role was the brief but iconic performance as Jeff Spicoli in 1982’s Fast Times at Ridgemont High.
Penn has been nominated for five Oscars and won two for Best Actor, for Mystic River and Milk. Those were hardly his only brilliant performances, though, so let's take a look at some of the best movies and parts from Sean Penn.
8 This Must Be the Place
This Must Be the Place paired Sean Penn with Frances McDormand for a powerful and bizarre look at an aging rock star who takes up his dead father’s quest to hunt down a Nazi war criminal. As Cheyenne, Sean Penn embodied the visage of a goth rocker, following in The Cure’s Robert Smith’s fashion (and hair and makeup) footsteps. He is unrecognizable, both in the way he looks and in the soft, quiet mumbles and characterstics he relies on for the role. Say what you will about the weirdness in the movie around him, but Penn’s performance is classic.
7 The Game
In The Game, Sean Penn plays Conrad Van Orton, the brother to Michael Douglas’ Nicholas Van Orton; Conrad presents him with the bizarre, titular gift that is at the center of the plot. Director David Fincher infused the film with psychological terror as only he can. Penn was pitch-perfect as the brother with a grudge he takes out on his older sibling.
6 21 Grams
The title of 21 Grams refers to the weight a person allegedly loses automatically upon death, with some calling this the departed soul. Sean Penn plays a critically ill mathematician who receives a heart transplant, and his story is interwoven with that of the family of his donor and a reformed criminal. Like several earlier films from Alejandro Inarritu, 21 Grams was a 'hypertext' film which linked a large ensemble of characters through an intricate narrative. Penn’s performance, however, stands out in this critically acclaimed film, and was understated, quiet, and nuanced.
5 Fast Times at Ridgemont High
Fast Times at Ridgemont High has become a classic in the decades since its 1982 release, with Sean Penn’s portrayal of the slacker Jeff Spicoli being most iconic; he nailed the stereotypical California surfer/stoner dude. Remarkably, this was just Penn’s second film role and his first major film role. In an interview with Jimmy Fallon on The Tonight Show, Penn admitted that he blew the audition for the role of Spicoli on purpose because he had an attitude about auditioning back then. One of the casting department staff followed him out to his car and told him to drop the attitude and try again-- the rest is history.
4 I Am Sam
Sean Penn was nominated for an Academy Award for Best Actor for his role as the developmentally different Sam Dawson in I Am Sam. Sam is raising his daughter (played by Dakota Fanning), but once she turns seven and mentally surpasses her father, their life together is threatened. Penn absolutely embodied his character in this film in an astounding performance, though since its release it has garnered a lot of backlash, and the director now regrets casting someone outside the disability community.
3 Dead Man Walking
Dead Man Walking garnered Sean Penn his first Academy Award nomination for Best Actor. In the 1996 film, Penn plays Matthew Poncelet, a prisoner on death row who is an admitted white supremacist and an attempted terrorist bomber. Once again, Penn infused his character, a despicable human being, with real heart, forcing audiences to see the point of view of a man who is, in hopefully many cases, the complete opposite of us. Penn's humanity and gravitas elevated the drama into something truly serious.
2 Milk
As Harvey Milk, Sean Penn once again transformed himself into his character, the LBGTQ+ activist who created a Mecca for gay and lesbian people in the Castro District of San Francisco in the early 1970s. Director Gus Van Sant's playful, intimate film follows Penn in nearly every scene, winning him the Oscar for Best Actor for this role in one of the best LGBTQ+ films of the 2000s. He gave such a tour de force, powerful performance as the gay icon in Milk, that it's unfortunate he would later say things like "men have become quite feminized" and that there are "cowardly genes that lead to people surrendering their jeans and putting on a skirt.”
1 Mystic River
In Mystic River, Sean Penn plays Jimmy Markum, an ex-con whose daughter is murdered, forcing him to look into the roles his childhood friends (who suffered a tragedy in their youth, themselves) may have played in her death. Penn’s performance in this film is so powerful, he literally leaves the audience feeling as if they're going through everything he’s going through, leading to him winning the Academy Award for Best Actor for the role. He inhabits an ethically ambivalent, tortured, suspicious psyche, and is both victim and perpetrator in this heavy, heartbreaking film.