Spanning the 1990s through late 2000s Sean Penn has continued to work regularly as an actor, but during this era audiences were also reintroduced to him as a director and sometime screenwriter. His four films, The Indian Runner, The Crossing Guard, The Pledge and Into The Wild all further explored the personal, life conflicting stories he’s made the backbone of his career. The movie quartet, all Penn directed, is an organically creative extension of his performance work.
And it’s what Penn’s been able to do with each portrayal that has made him so arresting. Sean easily morphs into the flawed everyman, the lone outsider, the societal outcast, the flippant conscienceless badass, the perennial screw-up and the man-child from the wrong side of the tracks with easy aplomb. Each persona, gingerly cloaked in and bearing the paralyzing weight of their own sin-specific weighted bloody crown of thorns. But it’s their shared exposed nerve of vulnerability that makes you need them, love them, and empathize with them desperately each time they surface. Many of his various career characters collectively represent some of the shortcomings of the human race, but like a mirror Penn’s passionate performances regularly keep reflecting back to us that personally, we are all each a little bit of them. Compared to other leading man roles by the Toms: Cruise and Hanks (Penn’s Hollywood peers similar in clout, years in the business and popularity) Sean doesn’t care whether you ‘like’ his characters or not (and sometimes you shouldn’t) because as audiences, our attraction to them runs a little heavier, deeper and oft-times darker. We are hypnotically seduced by both their wrongs and charms and come back each time we are beckoned.
That’s what so fascinating about Penn’s performance as Harvey Milk. As the title character, Sean is the anti on-screen Penn. He’s sunshine personified with giggly eyes and a playful sense of humor. You not only love him, you like him a whole lot. The historical tale of the country’s first openly gay politician, Harvey Milk was the earnest and rare of politico. He was an equal parts combo of public servant—he rose to prominence eventually becoming an elected San Francisco Supervisor and gay rights activist—championing the mission personally and professionally to get homosexuals to live closet-free, equal lifestyles during the cause nomadic seventies.
Penn plays Milk quietly reflective, and earnestly loyal to his friends, lovers and colleagues united for his groundbreaking Mecca. His effeminate physical movements never betray homosexuals in stereotypical parody, but almost possess a dancer’s grace. And under director Gus Van Sant’s poetic tutelage, Penn all but freefalls from any heterosexual actor’s comfort zone to give the film’s gay love scenes a universal sensuality and purity. You’ve heard the legend that Denzel Washington warned Will Smith not to do any gay mouth kissing scenes in Six Degrees of Separation? Well, Sean never got that memo. His performance in Milk is the most valorous portrayal of a homosexual character by a straight actor in recent years. With each film he pushes boundaries, with each performance he outdoes his canvas of work and in the process he always reinvents himself. Milk earned Penn his second Oscar win because he was just that good. And that is why as long as Sean Penn is acting and directing, my eyes will continue to be cast upward, transfixed onto the big screen.
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