Actors inevitably change as they age, sometimes altering their screen personas dramatically in the process. After spending much of their early careers exuding restless energy, Tom Cruise and Brad Pitt became comfortable with stillness. Others, like Daniel Day-Lewis and Al Pacino, became bigger hams—which is not, in their cases, a bad thing, as anyone who’s seen There Will Be Blood (2007) and Heat (1995) can attest. But Sean Penn is a rare case—an actor who has always vacillated between delivering relatively naturalistic work and more expressionistic performances his whole career, with slight emphasis on the former in the 1980s and the latter in the 1990s. In the past decade or so, however, Penn has had a difficult time keeping track of which approach would fit better in which movies, with many of his larger-than-life performances feeling too mannered and his heaviest roles showing more fatigue than inspiration.
He’s an odd choice, then, to star in the soon-to-be-released action spectacular The Gunman from the French director of Taken, Pierre Morel. It’s the latest attempt to give a first-rate actor a chance to become a vigilante action star, but Penn has neither Liam Neeson’s gravitas nor Denzel Washington’s galvanic charisma. Penn the tough guy isn’t unbelievable, but it has come to a point where he’s never less interesting than when brooding.
This was not always the case. In some of his earliest roles from the 1980s and early ’90s, Penn made a name for himself as one of the most intense, committed young actors of his generation. He played a juvenile delinquent in Bad Boys (1983);a paranoid, coked-up drug dealer-turned-spy in The Falcon and the Snowman (1985); a young man turned against his criminal father in At Close Range (1986); a reckless police officer in Colors (1988); and an ethically conflicted undercover cop in State of Grace (1990). In these early roles, Penn is an exposed nerve—a troubled and volatile young man being pulled from all sides and barely holding himself together. He displayed angst with grace, yet always appeared ready to lash out. Penn’s violent encounters with the paparazzi and, more troubling, his reported physical abuse of then-wife Madonna suggested that this wasn’t that far removed from his own troubles. Whatever the case, Penn tapped into a level of fury in himself that rarely felt forced.
But Penn displayed a wider range in his first two performances alone. Immediately after a memorable debut as an irresolute and sarcastic, but highly moral, military school cadet in Taps, Penn turned to Amy Heckerling’s Fast Times at Ridgemont High (1982), where he gave one of the decade’s most indelible comic turns as stoner and surfer dude Jeff Spicoli. It’s as far removed from the majority of his work around it as can be, yet Penn never feels like he’s forcing an archetype. Rather, he plays every interaction with Ray Walston’s stern authoritarian teacher with total sincerity, as if coming to class late because the food line was too long or ordering a pizza in class was part of the syllabus. There’s a sense of discovery and play in each moment, suggesting that he could have been one of the great comic actors had he not gone down the serious route.
Penn occasionally punctuated this period of solemnity in the ’80s with more comic turns, but without the same level of success. His attempt to recapture the Spicoli magic as a dim-witted Southern crook in Louis Malle’s stillborn comedy Crackers (1984) feels as labored as his earlier creation felt organic. His one film with Madonna, Shanghai Surprise (1986), feels like an uneven blend of comedy and method straining, earning unfavorable comparisons from The Los Angeles Times to Dustin Hoffman’s Ratso Rizzo. And while Penn has moments in Neil Jordan’s convicts-pose-as-priests comedy We’re No Angels (1989)—his sermon on being kind to strangers is one of the few laughs in the film—he mostly resorts to mugging.
The one film that successfully taps into Penn’s skill at playing heightened characters is not, oddly enough, a comedy. Brian De Palma’s Casualties of War (1989) might be the grimmest Sean Penn film of the period—a harrowing look at the wartime rape of a Vietnamese girl by a group of soldiers (Penn, John Leguizamo, and John C. Reilly) as one G.I. (Michael J. Fox) watches helplessly. As Sgt. Meserve, Penn starts out as a soulful, charismatic soldier and mercurially cranks up the macho bullshit, wildly swinging weapons and repeatedly calling Fox’s character a “faggot.” It’s an intimidation tactic, not an actor losing control, and it’s the first sign of what Penn could do when bringing wild man theatrics to graver material.
He showed his aptitude for duality again in 1993 after a three-year break from acting when he teamed up with De Palma again for Carlito’s Way. Shaving part of his head and giving himself a perm that makes him look vaguely like Larry Fine, Penn plays the sleazy mob lawyer Dave Kleinfeld as a more outrageous character than any of the gangsters surrounding him. His character possesses multiple faces—Dave the respectable lawyer, Dave the liar, Dave the nervy cokehead—and he pulls off each shade of by making every scene a negotiation, some more successfully than others. It’s a big character, but Penn imbues Dave with a certain level of desperation that makes it simultaneously one of his biggest and most human performances.
That became Penn’s specialty in the 90s: portraying Capital-C Characters as human. It earned him his first Oscar nomination as the convicted murderer and rapist Matthew Poncelet in Tim Robbins’ gripping death row drama Dead Man Walking (1995). Penn organically projects a macho façade that gradually falls away as Matthew accepts his guilt and his fate. He was a repeat Oscar nominee 4 years later as idiot savant guitarist Emmett Ray in Woody Allen’s fine comedy Sweet and Lowdown (1999). Penn taps deep into Ray’s exaggerated masculinity and wild man behavior while slowly revealing a sense of melancholy once he realizes he’s lost his true love.
His biggest high-wire performance of the era, in 1998’s Hurlyburly, suggests an even more wigged-out version of his Dalton from 1985’s The Falcon and the Snowman. But for all of his lunatic screaming and jittery mannerisms, Penn still finds a sense of play and humanity in his work. Not all of Penn’s bigger performances in the ’90s worked—She’s So Lovely (1997) won him the award for Best Actor at Cannes but his approach seems too over-the-top when paired with Nick Cassavetes’ flat visual style—but Penn was always daring. Plus, there was always a more grounded role (1997’s The Game and 1998’s The Thin Red Line) around the corner to help balance things out. Or, in the case of Oliver Stone’s underrated U Turn, his more sensible presence made all of the nutzoid supporting players seem all the more insane.
Then, around 2000, something broke. Penn started blending naturalism and theatrics together, with highly inconsistent results. His Oscar-winning performance as Jimmy Markum in Mystic River (2003) is impressive in its quietest moments, when he’s stewing over the loss of his daughter or shooting side-eyed shade to a neighborhood kid he doesn’t like much. But Penn likely won the Oscar for the handful of scenes where his character either breaks down or loses control and starts screaming, placing way too much emphasis on emoting rather than being. At its most benign, like in a scene where he cries for his daughter in front of an old friend, it’s merely annoying—with Penn signaling that the waterworks are coming long before the tears start to flow. At its worst, it turns him into a bad James Cagney knockoff, which shatters director Clint Eastwood’s measured, mournful mood.
This has become a constant problem with Penn’s recent work, where he’s started playing bigger characters as caricatures instead of plausible people. His Willie Stark in Steve Zaillian’s disastrous adaptation of All the King’s Men (2006) is less a Southern politician and more a surly creep who’s mush-mouthed and uncharismatic behind the scenes and a raving lunatic in the spotlight. His Mickey Cohen in Gangster Squad (2013) shoots for the kind of glorious cartoon Al Pacino played in Dick Tracy, but it lacks the playfulness that Pacino brought or that Penn might have displayed earlier in his career.
The nadir, no doubt, is his Oscar-nominated role in I Am Sam (2001). As Sam Dawson, a mentally disabled father with an IQ lower than his 7-year old daughter, Penn remains one-note and delivers a performance that’s not just bad but offensive. It’s his first role that shows signs of an actor begging for sympathy while drawing attention to his own transformative virtuosity rather than trying to get inside the head of a character. Penn isn’t helped by a script that treats Sam more like a magical, whimsical creature than as a person (not to mention the films set of straw man villains, who are unequivocally correct about Sam’s abilities to take care of a child). But Penn’s badly misjudged choice to play each of Sam’s tics at maximum volume is what reeks the most in this intellectually and emotionally dishonest film.
It’d be less frustrating if not for the fact that around the same time, Penn’s more low-key performances started to feel strained as well. Kathryn Bigelow’s bizarre arthouse misfire The Weight of Water (2000) shows Penn returning to the type of disaffected cynic he played so memorably in The Thin Red Line, but without the same fervor. Penn is far more engaged in the melodrama of Alejandro Gonzalez Inarritu’s misery-fest 21 Grams (2003), but he still can’t quite overcome the film’s oppressive portentousness.
He lapsed further into self-parody in Thomas Vinterberg’s disastrous It’s All About Love (2003), and by the time he co-starred with Naomi Watts in the ripped-from-the-headlines drama Fair Game (2010), Penn’s own bullying self-righteousness and self-seriousness seemed inseparable from his characters, making his speechifying self-consciously virtuous and insufferable. His only truly great serious performance of the new millennium, as an increasingly unhinged sad-sack salesman in The Assassination of Richard Nixon, now feels less like another winner from Penn and more like an uncharacteristically great performance. From the ’80s onward, Penn specialized at playing characters who were spiritually and emotionally exhausted, but by the early 2000s he mostly just seemed exhausted, with his cameo in The Tree of Life (2011) being a prime (if reasonably effective) example.
Some of this makes perfect sense given Penn’s public persona. In a 2001 interview, Penn expressed distaste for the actual process of acting and he’s hardly the only performer whose hit-to-miss ratio got wonky after he hit middle age. But Penn grew less interested in getting under the skin of his characters and became more reliant on shallow disaffection, and it’s dispiriting to see most of his work drained of the vitality that made him such an exciting presence for the first two decades of his career. Something needs to be jump-started in him, lest he succumb to an eternal late-career crying and yelling jag.
The answer may be easier than it seems. Penn’s initial shift from angry young man roles to big characters showed a new sign of his talents in the ’90s, and a similar shift is evident in two recent performances. While Penn’s outwardly frustrated routine has become just that—routine—he’s positively inspired in roles that allow him to be lighter and more humorous. Although it sounds like a bait-y biopic performance on paper, his work as Harvey Milk in Gus Van Sant’s Milk (2008) saw him chucking out the tortured method antics and playing a funny, sweet, empathetic, and slightly mischievous man—which kept his portrait of Milk from feeling like an impersonation or a righteously embalmed hero. For the first time in years, Penn acted in the moment again.
He’s equally strong in Paolo Sorrentino’s oddball road trip movie This Must Be the Place (2011), which sees him playing a Robert Smith-haired rock star who’s hilarious precisely because he’s so depressive. His effeminate, soft-spoken monotone and half-hearted giggle hides someone who’s masking real pain, and its essentially comic nature makes his character’s angst far more compelling than that of his recent dramatic counterparts. Both of these performances saw Penn return to the charm and good humor he exhibited in Fast Times at Ridgemont High, and, not coincidentally, they’re his most inspired performances in years. Odd as it may seem considering his general humorlessness in real life—and, in the case of his recent green-card remark at the 2015 Oscars to friend Alejandro Gonzalez Inarritu, his poor delivery of a questionably-timed joke—Penn might be best served by comic performances now.
Or, alternatively, Penn could take a break altogether and commit to the other thing he’s good at: directing. In the early 90s, Penn claimed he was retiring from acting to turn to directing, and he made an impressive debut with 1991’s The Indian Runner. Based on the Bruce Springsteen song “Highway Patrolman,” the film displayed Penn’s remarkable sense of place and skill with actors. Even as the film laid on the macho poetics a bit thick, it still showed a distinctive personality of someone wrestling with human nature—conflicted by the need to conform and the need to break free. Roger Ebert, in his review of the The Indian Runner, suggested, not implausibly, that the film displayed the two sides of Penn: the hothead and the soulful young man.
At any rate, he seemed reenergized when he returned to acting with Carlito’s Way. His sophomore effort, The Crossing Guard (1995), further showed his directorial chops and vision. And even when his acting track record became spottier in the 2000s, he managed to direct two first-rate films with the underrated thriller The Pledge (2001) and the acclaimed Into the Wild (2007). His films showcase his contemplative nature and his view of violence as both an affront to nature and an inseparable element of it (shades of Malick’s influence). The films he directed demonstrate his interest in men trying and failing to prove themselves in a harsh world. They also show how Penn brings out the best in actors: Jack Nicholson’s meditative performance in The Pledge is his best post-’80s performance, while Into the Wild shows, long before she won a Cesar award for Olivier Assayas’ The Clouds of Sils Maria this year, that Kristen Stewart is one hell of an actress when paired with the right material.
Penn’s fifth film as a director, The Last Face, comes out this year. Although its plot, which focuses on aid workers in Africa, sounds more prestige-y and issue-driven than his past efforts, Penn’s track record so far is so strong and his cast (current partner Charlize Theron, as well as Javier Bardem, Adele Exarchopoulos, Jean Reno, and Jared Harris) is so impressive that it’s difficult not to be a little excited by its potential. If it pushes Penn to direct more and keep better focus on what he wants to achieve as an artist, all the better. His voice—whether comedic, quarrelsome, or acutely psychological—is a distinct one, and the world deserves more of it—as long as he doesn’t feel the need to shout it.