Sean Penn on Daddio, Superpower and his relationship with acting

Sean Penn

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Sean Penn rarely gives interviews – he and the press have not always gotten along well, to say the least – but last week the revered actor and filmmaker met at his Malibu home with The Hollywood Reporter'S Awards Chatter Podcast for an in-depth conversation about his life, career and latest project, Papadioan indie, released last Friday, of which he is particularly proud.

Penn sits in a small, light-filled room that he recently redesigned himself. The walls are lined with photos of his late parents, his two children and himself, along with many other global stars he has met on his travels as an activist. He has white hair, puffs on cigarettes, speaks softly and is much more warm-hearted than his reputation suggests. At 63, divorced three times and currently single, he seems to have found a certain degree of peace – at least when one of his large dogs isn't jumping against the glass door trying to get his attention.

Over the course of a career that now spans nearly half a century, Penn has given unforgettable performances in films such as the 1982 I think I'm standing in the forest1995s Dead man walks1997s Sweets and interesting facts2001s I am Sam2003s mystical river And 21 grams2008s milk2011s The Tree of Life and 2021 Liquorice pizza; and directed films such as The Indian runner1995s The school crossing guard2001s The promise and 2007 Into the wild.

The latest film directed by Penn, Aaron Kaufmanwas 2023 Superpowera documentary about Ukraine and its president Volodymyr Zelensky after the attack on the country by Putin's Russia in February 2022 – a time during which Penn remained in Kyiv at great personal risk and refused to leave in the hope of shedding light on what was happening. Penn and Zelensky have become close friends, and Penn even tried to give the politician, a former actor/comedian, one of his two Oscars (Penn does not reveal which one); Zelensky said he would not keep it, but at Penn's urging agreed to keep it as a token of their relationship until the war is won.

Penn's off-screen activities have polarized people for decades – something he admitted when accepting his second Oscar, jokingly saying, “I know how hard I make it to appreciate myself” – but few with taste have ever questioned his talent on screen. He was awarded the New York Times as “an actor of considerable talent” who performs “astonishing self-transformations” and is “perhaps the best actor of his generation, and also the most influential”; by the Los Angeles Times as “the leading actor of his generation, a shining talent in the tradition of Dean, Brando and De Niro”; and by none other than Meryl Streep as simply “brilliant”.

His work has been recognized not only with two Oscars, but also with 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 awards from all three of the major international film festivals, Cannes, Venice and Berlin; the Producers Guild of America's Stanley Kramer Award for “illuminating provocative social issues,” a César honorary award for professional achievements, and the list goes on.

But if you think Penn is resting on his laurels, you should take a look at this. Papadioin which he delivers one of his boldest performances to date. In the film, which the debut filmmaker directed Christy Hall and produced by and with Penn's friend and neighbor Dakota Johnsonwhich had its world premiere at the Telluride Film Festival last fall but whose release was held back until June 28, he plays a talkative, urbane New York taxi driver who has a deep and searching conversation with a passenger (played by Johnson) while chauffeured her from JFK airport to midtown Manhattan.

Fans of his performance include Deadline's Todd McCarthywho wrote: “Penn is at his absolute best here and offers an incredibly captivating performance,” and The Hollywood Reporter'S Stephen Farberwho enthused: “Penn has shown versatility in the past. He has played many tough guys, but in his Oscar-winning role in milk. Here he exudes some of the same charm and is a perfect foil to Johnson. In 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 replies, “Sometimes.” The look on Penn's face shows the eloquence that a gifted actor can muster without saying more than a single word.”

During this episode of Awards ChatterPenn speaks openly about his journey to a company that blacklisted his father (the actor and later director). Leo Penn), by an acting teacher (Peggy Feury) and theatre director (Art Wolff) that changed the course of his life; why, after breaking into the film scene in the early 1980s, he soon lost his love of acting and found himself increasingly drawn to directing; how he eventually got drawn into his most famous roles – and mastered the challenges of those roles; what he plans to do next (reprising his role alongside Johnson in a stage version of PapadioDirecting a Broadway musical and another film by The school crossing guard are all possibilities); and much more.