A Look at the Career of Sean Penn

Today we revisit the first installment of Friday Film-O-Rama, and deconstruct the stellar career of Sean Penn. He burst onto the scene in 1982 as Jeff Spicoli in Fast Times at Ridgemont High and his portrayal of the ultimate California surfer-stoner dude became a part of our pop culture lexicon, and remains so to this day. We'll look at pivotal moments in Penn's career, at what he's got coming out soon, and finally, we'll wrap up this Penn Retrospective with a list of DVDs for you to go out and rent to complete your Pennucation.

Spicoli may be Penn's first breakout role but it also signaled the beginning of a Penn mythology - his complete transformation from character to character. In 1981, Penn played the role of Cadet Alex Dwyer in Taps. His character was a military school student involved in a movement to stop his school from being torn down to build condos. Can you imagine Spicoli being so motivated? This was just the first of many transformations this versatile actor has made in his career.

In fact directly after doing the Military school cadet to Spicoli transformation, Penn again did an about face, playing Mick O'Brien in Bad Boys. Mick's character is in prison for murder, albeit accidental murder. Penn played this role with such a perfect intensity that you could really believe he was Mick O'Brien, murderer.

This three film 1981 to 1983 period in Penn's early career set a mark for him to follow for years after. He sought out roles that were challenging, characters with depth, often, as in the case of Spicoli, hidden depth; and roles that were diversely different. He went from being a military school cadet to Spicoli to a murderer. And his commitment to each character was absolute.

In the mid-80s Penn had a famous penchant for getting punchy with the paparazzi that stalked him and then wife Madonna. This bad boy image would stick with him for eons, long after he'd settled down with Robin Wright Penn and channeled his anger towards political activism.

From 1986 to 1989 Penn again took on a three-film character arc that showcased his talent and his agility with dark subject matters.

In 1986, Penn tackled the role of Brad Whitewood, Jr. in At Close Range. This film tackled a troubled relationship between a father and son who were members of the same gang. Penn's performance showed the steely determination of a young man who in running from his father ends up following in his exact footsteps. Christopher Walken played Penn's dad, and the intensity coming off these two actors as they play off of one another is haunting.

Then, to borrow a term from the recent elections, Penn flip-flopped into the role of Officer Danny McGavin in the 1988 film Colors. He was the rookie cop to Robert Duvall's veteran. He was the one who was convinced he could make the difference in L.A.'s gang wars. And he was, once again, walking on the opposite side of the line from his character in At Close Range.

In the 1989 Brian De Palma film, Casualties of War, Penn played Sgt. Tony Meserve, the ringleader of a quartet of soldiers in Vietnam who kidnap and repeatedly rape a young girl from the village. They have at her until she is senseless and broken. In this choice of roles, Penn has combined facets of previous roles. You have his signature penchant for darker subject matters, and you have a blending together of the cop from Colors and the bad boy from At Close Range.

From 1995 to 1998 Penn's performances took on a more layered aspect. This was when we started to hear the word "Oscar" mentioned in regards to his roles. And he was, in fact, nominated for an Academy Award for his portrayal of a convicted serial killer on death row in 1995's Dead Man Walking.

This film starred Susan Sarandon as a nun offering solace to a serial killer and working with him to receive a stay of execution from the governor. The nun begins to sympathize with the killer as well as with his victims and their families. Penn's killer's calm and composed façade belie the violence of his crimes, shown in flashback. The film was directed by Tim Robbins , who also wrote the adapted screenplay based on the Nun's true life experiences. What Robbins showed and Sarandon and Penn delivered, was a haunting paradox. The nun could care for Penn while abhorring what he did.

n 1997 Penn took the role of Conrad Van Orton in The Game. He was the supporting player to Michael Douglas (MDOUG), but also the antagonist. His gift to his brother was the live action game that consumed and almost destroyed his life. Penn's screen presence is so strong, that even in this supporting role, he was commanding.

In 1998, he starred in Hurlyburly - the adaptation of the David Rabe play - about a group of Hollywood players and wannabes whose lives intersect in a tragedy more interesting than any screenplay. Penn's Hollywood dealmaker was pitch perfect and I had to laugh at various points in this drama. Between Penn's well known real-life intensity, and my own background working at his talent agency, I had to wonder if his interpretation was true or if he was playing for comedic excess.

There are similarities between his characters in The Game and in Hurlyburly. Both have a cold arrogance to them that counteracts the depth of emotion in his Dead Man Walking serial killer.

In the most recent era of his career he has snagged the Oscar he has so richly deserved for years. From 2001-2003, Penn again took on a wide spectrum of roles. He was a retarded single father, a man whose daughter was killed, and a critically ill professor.

In 2001's I Am Sam, Penn gave a mesmerizing performance as Sam, the mentally retarded man fighting for custody of his 7 year old daughter. Penn was heartbreaking, and funny, and sad, and so completely became Sam that you never for a moment thought he was not actually retarded.

In Mystic River, Penn plays one of a trio of childhood friends reunited as adults after Penn's teenage daughter is brutally murdered. His character of Jimmy feels the extreme rage any parent would feel in this situation, but the criminal, Mafioso-type side of him seeks cold hearted retribution. Jimmy is not a good guy, but he is a compellingly sympathetic character in this drama from director Clint Eastwood. And Penn won the Academy Award.

Released almost at the same time as 2003's Mystic River was 21 Grams, in which Penn played a college professor dying of heart failure who is drawn to a woman, played by Naomi Watts, coming to terms with the death of her husband and daughters. Penn's character Paul is in a loveless marriage and Watt's character Christina has just had the love brutally ripped out of her life. They are the same, yet also a study in contrasts. The two come together when Penn receives the heart of Watt's dead husband and seeks her out, not telling her his reasons. A dark and sad tale without redemption, 21 Grams showed the bleaker side of life.

Sean Penn has made his mark in Hollywood through his choices and the unique talent he possesses. He is one of the finest actors of our generation. Following is the Penn filmography, your homework. Rent them to see what I am talking about. His intensity seeps into you and pulls you into the story.