The Changing Roles of Sean Penn

by Helen Earnshaw | 9 March 2011

Fair Game

Sean Penn is widely recognised as one of the finest actors of his generation with two Best Actor Oscars under his belt - as well as a whole host of other performances that could have easily added to that tally.

He is back on the big screen this week as he reunites with Naomi Watts for Doug Liman's political thriller Fair Game.

So to celebrate the release of the movie we take a look at some of the best performances from one of the industry's greatest actors.

Dead Man Walking (1995)

Directed by Tim Robbins and also starring Susan Sarandon, Dead Man Walking is a fascinating and powerful drama explores the relationship between a condemned young convict and the nun who counsels him in the days leading up to his execution.

Only one film before Dead Man Walking, A Short Film About Killing by Krzysztof Kieslowski, and almost non since have tackled the issue of capital punishment so well.

It looks at the pain on both sides of the crime and Robbins, who also penned the script, highlights that there are no clear cut answers surrounding this tricky subject of if somebody takes a life should they in return lose theirs?

It's one of those very rare films that leaves an audience with issues and beliefs to discuss between themselves and question what they believe and why.

Sean Penn gives a powerful performance as the condemned Matthew Poncelet showing him as a disoriented character moving from arrogant to showing his fear and the remorse that he has hid.

The Thin Red Line (1999)

1999 saw Penn return to the war movie, after starring in Casualties of War back in 1989, when he teamed up with Terrence Malick for the Thin Red Line.

A World War II tale which focuses on a squad of American troops battling against the Japanese during the hellish battle of Guadalcanal Island.

There is a great philosophical aspect that hangs over the whole film as the characters question reasons behind the war and in particular life, as they potentially walk so close to death, leaving many issues unresolved when the credits role, much like life itself.

Malick's main theme behind the movie was to delve into the experience and psyche of soldiers at war looking at how they cope, or not, with what they see and how they band together under the most testing circumstances.

There's also an interesting relationship between Witt (Caveizel), who sees beauty and hope in life but doesn't want to serve in the army compared to First Sergeant Welsh (Penn) who has lost hope in everything and now just follows orders as a way to survive.

Mystic River (2003)

But it was 2003 and his role as grieving father Jimmy Markum that Penn was to finally gets his hands on an Oscar.

The movie, which was directed by Clint Eastwood, saw Penn teams up with Tim Robbins and Kevin Bacon.

With a childhood tragedy that overshadowed their lives, three men are reunited by circumstance when one loses a daughter.

Penn, as well as Bacon and Robbins, give haunted performances in this movie as they are plagued by the past and now destroyed by the present.

Penn's grief is so powerful as his eldest daughter is murdered and it's just the sad existence that really gets under your skin.

21 Grams (2003)

Penn was destined to win an Oscar in 2003 as he produced as equally worthy performance with 21 Grams, which would have won if he hadn't have been nominated for Mystic River.

The Alejandro González Iñárritu directed project may not be the most cheery movie that you will ever see... but boy is it good!

A freak accident brings together a critically ill mathematician (Penn), a grieving mother (Watts) and a born-again ex-con (Del Toro). A freak accident brings together a critically ill mathematician (Penn), a grieving mother (Watts) and a born-again ex-con (Del Toro).

21 Grams is a very intelligent and well written movie that boasts some of the finest acting that you are likely to see.

The movie dissects the ideas of life and death as well as re-birth and second chances that will leave you asking you own questions.

Milk

The Gus Van Sant movie was the last time that we saw Penn on the big screen, back at the beginning of 2009, in the biographical movie Milk.

The story of Harvey Milk, and his struggles as an American gay activist who fought for gay rights and became California's first openly gay elected official.

This movie looks at the equal treatment of people and one man's brave quest to stand up against hatred.

Penn picked up his second Best Actor Oscar for his riveting central performance.

Other great performances by Penn include Casualties of War, I Am Sam, The Assassination of Richard Nixon and Sweet and Lowdown.