Oscar Justice: Sean Penn

Welcome to Oscar Justice, a weekly feature at Ice Creams for Freaks.  It’s a simple concept: I give an Oscar to someone who rightfully deserved it, then I follow the repercussions down the line until I am satisfied.

This week on Oscar Justice: Sean Penn in Dead Man Walking


1995 Best Actor, Dead Man Walking – Lost toNicholas Cage, Dead Man Walking
1999 Best Actor, Sweet and Lowdown – Lost to Kevin Spacey, American Beauty
2001 Best Actor, I Am Sam – Lost to Denzel Washington, Training Day
2003 Best Actor, Mystic River – WINNER
2008 Best Actor, Milk – WINNER


Sean Penn was not initially seen as an acclaimed actor.  After a few bit parts, his first prominent role was alongside Tom Cruise and Oscar winners George C. Scott and Timothy Hutton in Taps.  He followed it up with his most famous role, as the stoner icon Jeff Spicoli in Fast Times at Ridgemont High.  He ascended to a young hearthrob in films like Bad Boys, The Falcon and the Snowman, Colors and Casulties of War.  

For a time, it seemed that his personal life would be more prominent than his acting work until 1993 when he won critical acclaim and critic’s prizes for his role in Carlito’s Way.  He earned his first Oscar nomination in 1995 for the lead role as a death row inmate in Dead Man Walking.  Despite a number of critical accolades, Penn came up empty on Oscar night.

Penn would rack up Oscar losses three more times before his first win in 2003, which he followed up with another victory in 2008.


Sean Penn defeats Nicholas Cage at the 1995 Oscars for Best Actor in a Leading Role.


Never before and never since has a Sean Penn role been more suited than his role as Matthew Poncelet.  Penn keeps his hardened exterior while able to peel back the layers of sensitivity and regret under that veneer.  Additionally, his platonic chemistry with co-star Susan Sarandon is the lynchpin on which the entire film relies.  Sarandon attempts to cut to the core while Penn stays steely until his walls are broken down and everything comes rushing to the surface.

Penn is such an enigmatic actor, the trick of containing him in a cell for the majority of the film is the true wonder.  He is bursting with energy, but is forced to keep it all together.  The lasting impact of the film has diminished as the years have gone by, but Penn’s performacne has continued to endure.  I just wish he could have the real Oscar to pair with Sarandon’s Oscar night victory.


This is where things get hairy.  I am by no means giving Penn three Oscars, so let’s take away the 2003 victory and give it to the man that everyone saw as the runner-up in Bill Murray for Lost in Translation. As much as I like Penn’s performance in Milk, he beat another powerhouse performance in Mickey Rourke in The Wrestler.  That performance is a bolt of lightning in an otherwise middling career, so I am willing to give the statue to Rourke.

The question then becomes: does Nicholas Cage need an Oscar?  I would argue that despite all the financial misgivings aside, his two Oscar nominations were very well deserved and should not be counted against him.  Is he a kook?  Maybe, but his performance in Adaptation is a masterclass in how to play two distinct characters in the same film.  Cage gets the Oscar in 2002 over Adrien Brody.  Brody has only the one nomination and win, so he leaves Oscar-less.  Brody has his own personal demons and his career has stalled a bit, but he is still working and may show back up in the Academy’s good graces one day.


Sean Penn wins Best Actor in 1995 over Nicholas Cage
Nicholas Cage wins Best Actor in 2002 over Adrien Brody
Bill Murray wins Best Actor in 2003 over Sean Penn
Mickey Rourke wins Best Actor in 2008 over Sean Penn

All Oscar Justice category fixes

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