On The Late Show to promote his new novel Bob Honey Who Just Do Stuff (initially written as his nom de plume Pappy Pariah), Sean Penn referred obliquely to his long and storied history of being a very public prick by suggesting to Stephen Colbert that readers might enjoy his book “despite being predisposed to loathe its author.” And while Penn wasn’t exactly ornery during their two-segment talk on Monday’s show, Colbert had his hands full wrangling the typically intense actor, director, author, and activist. Chain smoking like The Late Show was the 1960s Tonight Show, and sporting a thoroughly disheveled look all over, Penn fielded Colbert’s gingerly probing questions on subjects like Penn’s recent announcement that he’s “fallen out of love” with acting, his reportedly sledgehammer satirical novel, and the American political situation which Penn says spawned the violent misanthropy in Bob Honey Who Just Do Stuff. He also made a cryptic reference to Netflix “paying off settlements,” which he and Colbert left hanging. (Form your own theories there.)
Colbert noted that the book—about “a septic tank salesman turned assassin who kills old people with a wooden mallet,” and who may or may not turn his skills toward the newly elected president, who may or may not sound an awful lot like Donald Trump—reads like something written under the influence of “ayahuasca tea.” Penn called that more or less accurate, describing his book as an experience akin to “the conversation once a year with the drunken uncle,” and admitting that, at 57, and coming off an election that put Donald Trump in the White House, “idealism gets chipped a bit.” While Penn’s deliberate speech (Penn blames some mid-flight Ambien) and dour messaging about the country, and his career, and frequent asides recalled another recent, challenging Late Show interview, the possibly former actor came to life when praising the courage and idealism of the Parkland, Florida students who, as he said, endured “combat-level horror” and still found the will and maturity to organize this past weekend’s March For Our Lives. Agreeing with Colbert that this unprecedented mobilization of young people in the political process is a hopeful sign, Penn posited that he might be moved to “write a less dystopian book” after November’s midterms.
For his part, Colbert didn’t press Penn on allegations of abuse that have dogged him for decades. (And which throw his novel’s thinly veiled criticism for the burgeoning Me Too movement in Hollywood into especially stark relief.) Colbert did take Penn gently to task for his incessant smoking, noting that he wants Penn to be around for a long time, which elicited Penn’s gallows joke, “It’s job security for oncologists.” Penn might (or might not) be giving up acting (whose compromises he compared unfavorably to the artistic freedom of novel-writing). But, as far as performances go, watching Penn be himself under Colbert’s questioning was, in equal measure, as fascinating and off-putting as the signature Sean Penn film role.