Sean Penn rarely grants interviews — he and the press haven’t always gotten along, to say the least — but last week, at his home in Malibu, the venerated actor and filmmaker sat down with The Hollywood Reporter’s Awards Chatter podcast for an in-depth conversation about his life, career and most recent project, Daddio, an indie, released last Friday, of which he is particularly proud.
Seated in a small, light-filled room that he recently re-designed himself, the walls of which are covered with photos of his late parents, his two children and himself alongside many of world figures he has encountered in his travels as an activist, Penn, sporting a shock of white hair, puffed on cigarettes, spoke softly and was far warmer than his reputation would suggest he’d be. At 63, thrice divorced and currently single, he seems to have found a measure of peace — at least when one of his large dogs isn’t jumping up against the glass door trying to catch his attention.
Over the course of a career that now spans nearly a half-century, Penn has given unforgettable performances in films such as 1982’s Fast Times at Ridgemont High, 1995’s Dead Man Walking, 1997’s Sweet and Lowdown, 2001’s I Am Sam, 2003’s Mystic River and 21 Grams, 2008’s Milk, 2011’s The Tree of Life and 2021’s Licorice Pizza; and directed films including 1991’s The Indian Runner, 1995’s The Crossing Guard, 2001’s The Pledge and 2007’s Into the Wild.
The most recent film that Penn directed, with Aaron Kaufman, was 2023’s Superpower, a documentary about Ukraine and its president Volodymyr Zelenskyy in the aftermath of the attack on that country by Putin’s Russia in Feb. 2022 — a time during which Penn, at great personal risk, was in and refused to leave Kyiv, hoping to shine a light on what was taking place. Penn and Zelenskyy have become close friends, and Penn even tried to gift the politician, a former actor/comedian, one of his two Oscars (Penn won’t divulge which); Zelenskyy said he would not keep it, but, at Penn’s insistence, agreed to hold on to it as a token of their relationship until the war is won.
Penn’s off-screen activities have polarized people for decades — something he acknowledged when he accepted his second Oscar by cracking, “I do know how hard I make it to appreciate me” — but few of any taste have ever questioned his on-screen talent. He has been described by the New York Times as “an actor of sizable gifts” who makes “amazing self-transformations” and “may be the best actor of his generation, and also the most influential”; by the Los Angeles Times as “the leading actor of his generation, a blazing talent in the tradition of Dean, Brando and De Niro”; and by no less an authority than Meryl Streep as simply “brilliant.”
His work has also been recognized with not just the two Oscars, but also SAG, Golden Globe, Critics Choice, National Board of Review, National Society of Film Critics, Los Angeles Film Critics Association, New York Film Critics Circle, Gotham and Spirit awards; acting prizes from all three of the biggest international film festivals, Cannes, Venice and Berlin; the Producers Guild of America’s Stanley Kramer Award for “illuminating provocative social issues”; an honorary Cesar Award for career achievement; and the list goes on.
But if anyone thinks that Penn is resting on his laurels, they should watch Daddio, in which he gives one of his most audacious performances yet. In the film, which was directed by first-time filmmaker Christy Hall and produced by and costars Penn’s friend and neighbor Dakota Johnson, and which had its world premiere at last fall’s Telluride Film Festival but was held for release until June 28, he plays a chatty, worldly-wise New York City cabbie who gets into a deep and probing conversation with a passenger (played by Johnson) while shepherding her from JFK Airport to midtown Manhattan.
Fans of his performance include Deadline’s Todd McCarthy, who wrote, “Penn is at his absolute best here in a tremendously engaging performance,” and The Hollywood Reporter’s Stephen Farber, who raved: “Penn has shown versatility in the past. He has played plenty of tough guys, but he exuded humor and warmth in his Oscar-winning role in Milk. Here he channels some of that same charm and makes a perfect foil to Johnson. During the course of their conversation, Penn speaks of two failed marriages and recalls privileged moments in his first marriage. Johnson asks if he misses his wife, and he answers, ‘Sometimes.’ The expression on Penn’s face demonstrates the eloquence that a gifted actor can summon without saying more than a single word.”
During this episode of Awards Chatter, Penn speaks candidly about his path to a business that had blacklisted his father (the actor-turned-director Leo Penn), by way of an acting teacher (Peggy Feury) and theater director (Art Wolff) who changed the course of his life; why, after bursting on to the film scene in the early ’80s, he soon fell out of love with acting and found himself increasingly drawn to directing; how he wound up cast in — and tackling the challenges of — his most celebrated roles; what he is thinking about doing next (reprising his role opposite Johnson in a stage version of Daddio, directing a Broadway musical and making another film of The Crossing Guard are all possibilities); plus much more.
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