Since the 1980s, Sean Penn has been an American symbol of the cool, cigarette-smoking masculinity that peaked in the 1950s. His early films established him as a dedicated actor of brooding intensity, and he has spent the last forty years building a catalog of directorial work and gritty characters, mostly in dark trauma dramas: Dead Man Walking, Mystic River, The Tree of Life, Milk, The Thin Red Line, and I Am Sam. 

At sixty years old, Penn considers himself a “difficult person,” and over time he’s perfected the off-screen role of the artist-provocateur. In 2015, he dropped his famous and vexatious “Who gave this son of a bitch his green card?” joke at the Oscars, when presenting an award to Alejandro González Iñárritu, who directed Penn on 21 Grams, and incidentally, found the comment amusing. That same year he conducted a controversial Rolling Stone interview with El Chapo, a man the US DEA has referred to as the “godfather of the drug world.” Penn wrote a long-form essay that he hoped would develop the public’s thinking around the war on drugs—it didn’t, and Penn considers it a failure. Likewise, in 2018, he criticized the #MeToo movement for lacking nuance and dividing men and women. On The Today Show, he said, “This is a movement that was, you know, largely shouldered by a kind of receptacle of the salacious”—a comment that was analyzed by several publications for its perplexing, quasi-poetic message.