Shoulda Been Oscar Contenders: Sean Penn in Carlito’s Way

Continuing with my new series covering performances that could have warranted some Oscar attention, I move to my second post in the Supporting Actor race of 1993. The first one centered on Val Kilmer as Doc Holiday in Tombstone. As a reminder, the actual five nominees were a strong grouping with Tommy Lee Jones emerging victorious for The Fugitive. The other nominees: Leonardo DiCaprio in What’s Eating Gilbert Grape, Ralph Fiennes for Schindler’s List, John Malkovich for In the Line of Fire, and Pete Postlethwaite for In the Name of the Father. 

Another notable performance for that derby: Sean Penn in Brian De Palma’s Carlito’s Way. Almost unrecognizable as a sleazy coked up lawyer with an unforgettable hairdo, Penn managed to steal scenes from Al Pacino’s title character. Had his work been included here, it would have marked his first nod. Two years later, he achieved that with Dead Man Walking. Four more nominations (all in Best Actor) would follow with two victories in 2003’s Mystic River and 2008’s Milk as well as 1999’s Sweet and Lowdown and 2001’s I Am Sam. 

Yet his rare supporting turn alongside Pacino would have been fine with me for a sixth mention – even with the solid competition nearly three decades ago.

My Should Been Contenders posts will continue with another sturdy supporting turn from 1993…

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