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Sean Penn says he felt 'relieved' when directing his daughter for the 1st time

On Sunday TODAY, the Oscar winner described the emotions he felt when he directed his daughter Dylan in her first starring role in "Flag Day."
/ Source: TODAY

Sean Penn remembers one palpable feeling that stood out above the rest on his first day directing his 30-year-old daughter in the new movie "Flag Day."

The drama is based on the life of notorious counterfeiter John Vogel, played by Penn, 61, who tries to win back the respect of his daughter, played by Dylan Penn in her first major starring role. It also marks the first time she has been directed by her father.

"It wasn't until the first day of shooting, the first scene we shot together, when she just nailed a long scene," Sean Penn told Willie Geist in a sit-down interview on Sunday TODAY. "I remember immediately being thrilled, admiring, moved. But mostly relieved."

Dylan, who is Penn's daughter with ex-wife Robin Wright, made her acting debut in the 2015 horror film "Condemned" and has since acted in a handful of films. Penn found a project he thought they could do together and decided to act and direct in the same film for the first time.

"I had been sent the script, and I got to about page 30, and that's when my daughter's face got imprinted on that character in a way that I'd occasionally had happen with other actors, but not to the point where it could now only be that face for me," Penn said.

The father and daughter walked the red carpet together last month ahead of "Flag Day" showing at the 74th Cannes Film Festival. Penn's son, Hopper, 27, also appears in the movie.

Hopper Jack Penn, Dylan Penn, Sean Penn and Katheryn Winnick attend the "Flag Day" screening during the 74th annual Cannes Film Festival on July 10, 2021.
Hopper Jack Penn, Dylan Penn, Sean Penn and Katheryn Winnick attend the "Flag Day" screening during the 74th annual Cannes Film Festival on July 10, 2021.Stephane Cardinale / Corbis via Getty Images

As a veteran of almost 40 years in the movie business with a pair of Oscars on his résumé, Penn has seen enough to believe his daughter is ready for what comes with the limelight.

"She kind of got born with a sort of wisdom of soul, and I think that she'll handle this well," he said.

Acting and directing in the same film was a novel experience for Penn, but not one he is eager to repeat.

"So there are people who are wired for that,'' he said. "For me, I have noticed in my life that I am overdrawn to multitask, and it puts an incredible stress on it. Directing is a 17½-hour-a-day job anyway. The idea of going home to learn lines each night with everything else going on was too much."

The only thing that might get him back on both sides of the camera is another chance to work with Hopper and Dylan.

"I suppose if I found something that I identified as strongly with my son as this that I did my daughter, I would certainly direct my kids again," he said. "Dylan's side of that story is that the next time we're on a set together, she's directing."

Acting is the Penn family business, as both of Penn's parents were actors while he was growing up in Malibu, California.

"I invited my parents to my first play and (my mother) came backstage afterwards, and she said, 'You were terrible,'" Penn said while laughing. "You have to go to university and have something to fall back on.' She liked other performances better than that one, since that time."

From the iconic Jeff Spicoli in "Fast Times at Ridgemont High" to Oscar-winning performances in "Mystic River" and "Milk," Penn has become one of the most respected actors of his generation.

He also has become an activist and philanthropist who co-founded CORE (Community Organized Relief Effort) to bring relief efforts to Haiti in 2010 after a devastating earthquake. He will return to the country next week as it tries to recover from another deadly earthquake in addition to the assassination of Haiti's president.

"There's something biblical about it," he said about the situation in Haiti. "And my job, psychologically and practically, is to do what the Haitians are doing, which is put one foot in front of the other. And when I say 'my,' I really mean our organization's job. And that's what they're doing.

"They got in on day one with heavy equipment to aid in the search and rescue, and medical personnel. But I'm getting the daily reports and it's a real struggle."