Sean Penn is an Award-winning actor with a long history of celebrated performances that have made him one of the most successful actors in the industry. An intense, often highly-charged personality, Penn has created a number of very influential and iconic characters that have help shaped the very definition of the craft. But his talents lie well beyond what he does in front of the camera. Occasionally, over the past twenty-five years, he steps behind it and produces films that challenge and inspire. Here are three that deserve closer examination.
The Crossing Guard (1995)
Jack Nicholson plays Freddie Gale, a once devoted father who now suffers from deepening alcoholism while passing nights away at strip clubs, sleeping with prostitutes. Five years earlier, his daughter was killed by a drunk driver named John Booth (David Morse). Gale has been biding his time, waiting for Booth to be released from prison, slowly spiraling into worsening depression and obsession. When Booth is finally freed, Gale clumsily breaks into Booth’s trailer, intent on murdering him, but as fate would have it, the gun is not loaded properly and misfires.
Booth is a solemn man, riddled with unbearable guilt and decides not to call the police, and instead tells Gale he will allow him to kill him, but to please give him a few days to reflect on his life and enjoy a short time in freedom. Gale agrees to three days, and Booth takes the time to savor all he can, even meeting a woman named JoJo (Robin Wright), to whom he confesses a terrible secret about the accident that weighs heavily.
The film hinges on its performances and the manner in which these complex characters are played out, revealing a much deeper layer to these people than what might first appear. That’s a especially true with the relationship between Gale and his ex-wife Mary, played exceptionally well by Angelica Houston. Theirs is a embattled history that explains more about Gale than simply the fate of his daughter. And this is really the heart of the story, which Penn also wrote.
Penn’s second feature film is a little unstructured and perhaps concentrates a bit too much in what should have been more peripheral, but he shows a confidence in his storytelling abilities, giving his decidedly world-class cast room to find themselves. He has a sharp eye for the smaller details and wisely lets the action do the talking, judging us intelligent enough to connect the right dots. It pays off, and what we get is a tense, troubling story that works as both a character study and a gripping thriller.
The Pledge (2001)
Jack Nicholson joins Penn again, starring as Jerry Black, a Nevada police detective celebrating his retirement when a call comes in about the murder of a young girl in the woods. While not needing to go to the crime scene, he heads over anyway and is overcome by the harrowing death, but more so by the mistakes his fellow investigators are making. He speaks with the mother of the girl and pledges a promise that he will not rest until the real killer of her daughter is caught, even after police make an arrest of a mentally challenged Native American man named Toby (Beneico Del Toro), who it turns out, takes drastic action at the accusation.
Dissatisfied by his colleagues efforts to find the real murderer, he takes it upon himself to work alone, and eventually settles upon an area where he is sure the killer lives. He takes an apartment above a country store and gas station (making a comfy offer to the owner) at the center of a spree where girls that seem similar to the case have been killed. And from there, he isolates himself, soon befriending a woman named Lori (Robin Wright), a barmaid with her own issues. She has a young daughter, and the three become close, drawing Jerry into distraction though soon enough, questions arise as to whether Jerry will make a dangerous decision using the little girl to lure out the killer.
Nicholson is at his absolute best, a performance that is restrained yet tortured, marked by a sympathy that wholly pulls us in. He’s matched by Wright, who is desperately good as a mother in need of intimacy and security. Penn achieves a remarkable level of tension while never completely giving all the details, once again allowing the audience to make conclusions on their own but with a far more confident hand. His direction never overpowers the performances, but still maintains a strong presence. It’s a sensational entry and yet, still not his best.
Into The Wild (2007)
Based on the real life story of Christopher McCandless (played by Emile Hirsch), it follows a young man recently graduated from college who decides to wholesale drop out of society, donating all his money and burning his credit cards and identification. He then sets off in a beat-up car without telling his family, and drives across the country to experience the wild, his eyes always on Alaska. Along the way, taking the name Alexander Supertramp, he has impact on a few people’s lives, most notably Tracy Tatro (Kristen Stewart) who shows great interest him but is underage, and more importantly, Ron Franz (Hal Holbrook), a retired man who teaches him the craft of leatherwork and comes to care for the boy, offering him a permanent place to stay, though to no avail. McCandles eventually takes off on his own again, straight to the snows of Alaska and once there, faces his greatest challenge.
Without a doubt, Hirsch commands our attention as the troubled McCandles, a young man of great spirit and determination that never found his true place in this world, yet left behind an emotional trail of meaningful encounters. Holbrook too is incredibly effective, his performance one of immense power that feels deeply personal. But it is Penn’s vibrant and chilling adaptation of the Jon Krakauer book that grips most feircely. The writing is sharp and genuine, and his direction filled with breathtaking wide open vistas that give great weight to the land and nature all around the traveling man. It is that constant presence of the untamed world that always lingers, and Penn treats it like a character, giving it a dangerous beauty that we all know will hold the real fate of McCandles. Yet it is clear, despite the great work of the actors, that this is a film of urgent, passionate need for Penn, who embraces this with tempered, regretful hands, it all lasting with great impression. It’s a remarkable experience that puts Penn among some of the best directors in the business.