A Look at the Career of Sean Penn

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.