5 Matthew Poncelet, “œDead Man Walking”(1995)
Considered by many to be Penn’s quintessential role, this classic 90s drama from director Tim Robbins chronicles the relationship between Susan Sarandon’s nun Sister Helen, and soul patch-sporting, innocence-claiming death row inmate Matthew. Penn’s despair and sorrow, eventually revealed to be deep regret over deeds he actually did commit, are affecting beyond words.
4 Harvey Milk, “œMilk”(2008)
Penn effortlessly embodies the charm and bravery of openly gay 1970s San Francisco politician Harvey Milk, “œThe Mayor Of Castro Street,”in this stirring biopic. Penn puts on a persona that is superficially brighter than his more dour roles, but projects all of the strength and more of those typically tough characters, in one of 2008’s best films.
3 David Kleinfeld, “œCarlito’s Way”(1993)
When hitman/druglord Carlito Brigante left prison, he ultimately discovered his lawyer, Kleinfeld, had not only become a bigger crook then he, but was also a major cokehead, steadily losing his grip on sanity. Penn is at his absolute weaseliest here, alternating between frightened nerd and jumpy, impulsive psychopath, as he reaps the consequences of his swindling and manipulating. The Jewfro wig is a good fit.
2 Emmet Ray, “œSweet and Lowdown”(1999)
Pimp. Klepto. Gun lover. Train enthusiast. Greatest jazz guitarist in the world. Emmett Ray is all of these things and more in Woody Allen’s accounting of the misadventures of a hilariously arrogant and dysfunctional 1930s musician whose ego is his own greatest enemy. This sleazy blowhard is played off against Samantha Morton’s equally brilliant turn as his sweet deaf/mute girlfriend, Hattie.
1 Jeff Spicoli, “œFast Times at Ridgemont High”(1982)
The quintessential California surfer dude was idealized for all of America to see with this brilliantly spaced out performance that would prove to be one of a kind in Penn’s resume, making it that much better. Though one of many classic archetypes presented in this seminal teen film, none proved as enduring or hilarious as this chronically tardy stoner that everyone remembers from high school.