Top 10 Penn Moments

film reviews | movies | features | BRWC Five Serious Actors With Ridiculous Early Roles

By Kate Voss.

Sean Penn is a remarkable actor, capable of portraying everyone from a mentally handicapped father, to a teenage stoner, to a homosexual politician. His versatility and ability to create distinct personas in each role is unmatched. To celebrate Mr. Penn’s 53rd birthday, we take a look at 10 of his best on-screen transformations into the lives of very unique characters.

Fast Times at Ridgemont High (1982)



This was Penn’s breakout role which, in effect, helped bring the word “dude” to popular culture. He played a perma-stoned teenager who loved “tasty waves, a cool buzz.” While preparing for the role and to better understand the Jeff Spicoli character, Penn extinguished a cigarette in his palm. He got so into his character that he would only respond to Spicoli on set.

I Am Sam (2001)

In this heart-wrenching film, Penn plays the role of the mentally-handicapped father of Lucy (played by a young Dakota Fanning) who loves The Beatles and works at Starbucks. Penn, along with DiCaprio and Hanks, artfully showcased the struggles and issues that arise with mentally handicapped, and in I Am Sam, the extra struggles of being a parent.

Milk (2008)

In this film, Penn plays the role of Harvey Milk in a true story about the first elected openly homosexual politician in America. For this role, he won an Oscar for Best Actor in a Leading Role.

Dead Man Walking (1995)

Penn had a vocal and cosmetic transformation in this film to portray an inmate on death row for killing two teenagers who falls in love with a nun (played by Susan Sarandon). The Los Angeles Times said, “For this kind of straight-ahead movie to work, the acting must be strong without even a breath of theatricality, and in Penn and Sarandon, ‘Dead Man Walking’ has performers capable of making that happen.”

Mystic River (2003)

Penn plays Jimmy, an ex-convict living in Boston whose daughter is murdered. For the scene where Jimmy is crying hysterically over the death of his daughter, Penn requested that a tank of oxygen be standing by after he finished the take. For this role, Penn won the Oscar for Best Actor in a Leading Role.

The Assassination of Richard Nixon (2004)

In this film, Penn plays Samuel Joseph Byck, a used-furniture salesman who feels wronged by the world and attempts to hijack a plane to kill President Nixon. While the plot was not originally supposed to be a true story, while researching for the script, writers found a eerily similar story which they let influence the film. Penn agreed to star in the film six years before it was actually produced while still waiting for the film to be financed.

21 Grams (2003)

Penn plays the role of Paul Rivers, a critically ill math teacher whose life is told in non-linear fashion centered around a tragic car accident. Penn once again plays a grief-stricken man, similar to his Mystic River and I Am Sam performances.

Carlito’s Way (1993)

Penn is barely recognizable in this film where he plays David Kleinfeld, a Jewish lawyer and best friend to criminal Carlito. For the film, Penn shaved the hair on the front of his forehead to make it appear that he had a receding hairline and permed the rest of his hair.

Sweet and Lowdown (1999)

Penn plays a 1930’s jazz guitarist named Emmet Ray who falls in love with a mute in this film directed by Woody Allen. Penn was nominated for an Oscar for Best Actor in a Leading Role for this film.

This Must Be the Place (2011)

One of Penn’s more recent performances, he gets all dressed up to play the role of the soft-spoken wealthy former rock-star named Cheyenne. Jay Weissberg of Variety said, “Penn’s flawless performance has none of the mannered intensity that can mar his work, transcending the masklike qualities of eyeliner and lipstick with deadpan, childlike candor.”

Author Bio: 

Kate is a freelance entertainment and film writer for getdirecttv.org where she covers everything from new movie and TV releases to retrospectives on lost cinema classics. She loves creative writing, baking anything sweet and cooking vegetarian meals. She lives and works in Chicago.

By Kate Voss.

Kate is a freelance entertainment and film writer for getdirecttv.org where she covers everything from new movie and TV releases to retrospectives on lost cinema classics. She loves creative writing, baking anything sweet and cooking vegetarian meals. She lives and works in Chicago.


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Alton loves film. He is founder and Editor In Chief of BRWC.  Some of the films he loves are Rear Window, Superman 2, The Man With The Two Brains, Clockwise, Eternal Sunshine Of The Spotless Mind, Trading Places, Stir Crazy and Punch-Drunk Love.

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