Oscar Actors: Penn, Sean–Hollywood’s Most Talented Star?

I am not sure that there is such a thing as America’s Best Actor, but if there is, it must be Sean Penn.

Right now, Penn is getting the best reviews of his career for portraying Harvey Milk, the first openly gay man elected to political office, in Gus Van Sant’s exuberant biopic “Milk.”  He has already won acting kudos from the New York, the Los Angeles, the San Francisco, and other critic groups across the country.   Which means, he’s guaranteed to get another Best Actor Oscar nomination–his fifth–on January 22, when the nominations are announced.  Whether he wins or not is another question.  In this column, I would like to explore what makes Penn our most accomplished and versatile actor.


In style and approach, Penn is the kind of Method actor who brings to mind our trio of rebel actors, Brando, Dean, Clift, with a touch of the young Jack Nicholson.  However, unlike them, Penn is a “purer” actor, unburdened by an established screen image and a set of mannerisms.  This also distinguishes Penn (who was born in 1960) from other stars of his generation, such as Tom Cruise (born in 1962) or Brad Pitt (1963).


Early on, Penn’s career suffered from his hostility towards the press; in 1987, he got a six-month jail sentence for assault.  His short marriage to Madonna, and the one film they made together (“Shanghai Express” in 1986), also didn’t generate much positive publicity.  For better or worse, Penn has developed the reputation of a real-life anti-hero, an angry, politicized actor with a chip-on-his-shoulder and penchant for speaking his mind freely on any topic, including the Iraq War.


But let’s not confuse private with public life, off screen conduct and on screen work, personal politics with a more serious career consideration.  I would also like to leave aside Penn’s career as a director, which I have discussed in my book Cinema of Outsiders: The Rise of American Independent Film.

Screen Debut: Taps

From the beginning, Penn’s screen career has been marked by two factors, sheer brilliance, and the ability to immerse himself completely in the particular role he plays.  Penn made a striking movie debut in Harold Becker’s “Taps” (1981), a film in which a bunch of young actors, such as Tom Cruise and Timothy Hutton, also made an appearance.  But the film that put him on the movie and pop culture maps was Amy Heckerling’s “Fast Times as Ridgemont High” (1982), which became a cult item.  As Jeff Spicolli, the perpetually stoned surfer, he played the film’s most memorable character and registerd strongly in every scene.


Penn continued to develop and to impress as the shy, inarticulate boy in Richard Benjamin’s small-town melodrama, “Racing With the Moon” (1984), opposite Elizabeth McGovern.  In the mid to late 1980s, Penn gave three great performances, which flaunted a remarkable range.  As Daulton Lee, the drug-addict, directionless youth convicted of selling documents to the Soviet Union, in John Schlesinger’s fact-inspired “The Falcon and the Snowman” (1985), he stole every scene from co-star Timothy Hutton (also a member of his cohort).


He was touching and haunting as Christopher Walken’s troubled son in James Foley’s neo-noir “At Close Range” (1986), and again excelled as the rogue sergeant in Brian De Palma’s Vietnam War drama, “Casualties of War” (1989), in which his turn was both riveting and scary.


First Oscar Nomination: Convicted Killer


Though he had won a number of acting kudos, Penn began to get the Academy’s attention in the mid-1990s.  He received the first Best Actor nomination for his bone-chilling performance as the condemned man in Tim Robbins’ “Dead Man Walking” (1995), bringing commendable skill, authority, and even a slight touch of humanity to an unsympathetic role, a death-row convict charged with brutal sexual offences.


Penn was also good in Nick Cassavetes’s “She’s So Lovely,” which world-premiered at the 1997 Cannes Film Fest, a film that was a tribute to John Cassavetes (who wrote the scenario) as well as to the instinctive talent of Penn, who won the jury acting award.


The late 1990s brought several rewarding roles: He played Michael Douglas’ brother in David Fincher’s “The Game” (1997), registered strongly in Terrence Malick’s WWII drama, “The Thin Red Line” (1998), which was ensemble driven, and as coke-addict sleaze ball in Anthony Drazan’s “Hurly Burly” (also 1998), for which he won the Venice Film Fest prize.


Penn’s Second Oscar Nomination


Penn displayed immense charm as the jazz guitarist Emmet Ray, in Woody Allen’s period piece “Sweet and Lowdown” (1999), opposite Samantha Morton.  As the flawed musical genius, he showed Ray to be an egotistical cad, an emotionally crippled guy whose idea of a cool date is taking his girl to the garbage dump to watch him shoot rats.  That Penn succeeded in making viewers care about his unsympathetic character was a testament to his gifts; reportedly, he spent months studying jazz guitar to prepare for the role. 


Third Oscar Nomination: Mentally Challenged Father


Unfazed by any challenge, Penn has continued to choose courageously only demanding roles.  In Jessie Nelson’s “I Am Sam” (2001), for which he received his third Best Actor nomination, Penn rendered a towering performance, as a mentally challenged (autistic) father trying to hold on to his daughter against the courts and society’s norms, which elevated the film way above his sentimental manipulation.


Fourth Nomination–Winning the Oscar


In 2003, Penn gave not one but two outstanding performances.  In Clint Eastwood’s “Mystic River,” he shined as a bereaved, enraged avenging father (an ex-con) in a role that was both touching and threatening.  In the same year, Innaritu cast him as a dying university professor in his moving melodrama “21 Grams,” in which he shared the screen with Naomi Watts.


Milk: Fifth Oscar Nomination


And now comes “Milk,” a refreshing change of pace for Penn, after playing so many angry, troubled, violent and damaged men.  As the real-life politico, he succeeds in showing the happy side of a man, whose existence was defined by many tragedies in his personal life, stressing Milk’s desire for self as well as social acceptance, his wish to feel proud (or at least not ashamed because of his sexual orientation).  There’s charismatic magnetism and soft sweetness to Penn as Milk, which come across in his interactions with his lovers (James Franco and Diego Luna among them) as well as in his communication with his political entourage and co-workers. David Denby has astutely observed in the New Yorker: “Penn takes an actor’s craft and dedication to soulful heights, making a demand for dignity that becomes universal.”


Greatly assisted by director Gus Van Sant, Penn elevates “Milk” way above the story of one man’s life and death to the point where it becomes a timely statement about the uniquely American political process, a call to arms to ordinary people to get involved because they can make a difference, an invigorating reminder of what freedom and rights really mean in our society.


Perhaps the secret to Penn’s bravura work is that he doesn’t act like a leading man, but approaches his roles as characters actors.  He creates in minutia detail lived-in men, with all the physical and emotional baggage that comes along.   Even Penn’s detractors have to admit that he has become an astonishingly gifted actor, specializing in bringing complex and troubled anti-heroes to the big screen.  Penn has achieved an iconic status as an actor, without ever trying hard.


We would like to know your opinion.  Does Sean Penn deserve an Oscar nomination for “Milk”  Who do you think is America’s best actor