What is the best Sean Penn acting performance of all time?

Two Academy Awards, multiple nominations, and a fearless refusal to play it safe — Sean Penn is one of the most demanding and transformative actors of his generation. He's played stoners, saints, killers, and politicians with equal conviction. Which of these performances is his greatest?

1

Harvey Milk

The pioneering gay rights activist and San Francisco city supervisor in Gus Van Sant's biopic Milk (2008), earning Penn his second Oscar.

2

Jimmy Markum

A volatile ex-convict whose childhood trauma explodes after his daughter is murdered in Mystic River (2003), earning Penn his first Oscar.

3

Sam Dawson

A developmentally disabled father fighting the legal system to keep custody of his young daughter in I Am Sam (2001).

4

Matthew Poncelet

A death row inmate finding spiritual guidance from a nun in the final days before his execution in Dead Man Walking (1995).

5

Emmett Ray

A deluded, self-proclaimed jazz guitarist who idolizes Django Reinhardt in Woody Allen's Sweet and Lowdown (1999).

6

Jeff Spicoli

The eternally stoned, pizza-ordering surfer dude who became one of cinema's most beloved comic characters in Fast Times at Ridgemont High (1982).

7

David Kleinfeld

A corrupt, cocaine-fueled lawyer whose greed destroys everything in Brian De Palma's crime epic Carlito's Way (1993).

8

Sgt. Edward Welsh

A nihilistic platoon sergeant questioning the meaning of war in Terrence Malick's WWII epic The Thin Red Line (1998).

9

Cheyenne

A retired goth rock star embarking on a quest across America to find his late father's Nazi torturer in This Must Be the Place (2011).

10

Mick O'Brien

A young delinquent sent to juvenile detention who must face a brutal rival he wronged on the outside in Bad Boys (1983).

11

Samuel Bicke

A failing salesman and disillusioned everyman planning a shocking act of political violence in The Assassination of Richard Nixon (2004).

12

Sgt. Tony Meserve

A ruthless, morally bankrupt sergeant leading his squad in a Vietnam war crime in Casualties of War (1989).

13

Frank Buckley

A charming con artist seen through the eyes of his devoted daughter in Flag Day (2021), a film Penn also directed.