Sean Penn, with Daughter Dylan, Directs again in 'Flag Day'

Sean Penn, left, and Dylan Penn pose for portrait photographs for the film 'Flag Day', at the 74th international film festival, Cannes, southern France, Saturday, July 10, 2021. (Photo by Vianney Le Caer/Invision/AP)
Sean Penn, left, and Dylan Penn pose for portrait photographs for the film 'Flag Day', at the 74th international film festival, Cannes, southern France, Saturday, July 10, 2021. (Photo by Vianney Le Caer/Invision/AP)
TT

Sean Penn, with Daughter Dylan, Directs again in 'Flag Day'

Sean Penn, left, and Dylan Penn pose for portrait photographs for the film 'Flag Day', at the 74th international film festival, Cannes, southern France, Saturday, July 10, 2021. (Photo by Vianney Le Caer/Invision/AP)
Sean Penn, left, and Dylan Penn pose for portrait photographs for the film 'Flag Day', at the 74th international film festival, Cannes, southern France, Saturday, July 10, 2021. (Photo by Vianney Le Caer/Invision/AP)

Sean Penn is sort of done with movies.

He’s still making them, here and there. But Penn is mostly seeing out commitments he made years earlier. After those? He’s not so sure how much more he’s going to be acting or directing.

Penn, the 61-year-old maverick actor and sometimes filmmaker, is in many ways happily out of step with many of the prevailing winds in Hollywood. Streaming films? Franchise movies? So-called “cancel culture?” All of these things draw his ire, to various degrees. Meanwhile, Penn is dedicating more of his time to Haitian relief efforts and getting people vaccinated than he does to movies, reported The Associated Press.

All of that makes “Flag Day,” a new film Penn directed and co-stars in, a rarity for a once voracious actor who in the past decade has been a co-lead in only a few movies (“The Professor and the Madman,” “Gangster Squad”). In the father-daughter drama, which MGM will release Friday in theaters, Penn plays a larger-than-life but often absent and sometimes imprisoned father to daughter Jennifer (played by Penn's daughter Dylan Penn).

“I’m currently feeling with this movie incredibly lucky to have a movie that’s going to be a movie, that’s going to have a theatrical front,” Penn said in an interview last month. “I, as an audience, can be very into some of the things that are only streaming. But as a practitioner, not at all. To act in something, you take it in a certain stride. But as a director, the way I’ve always put it is: It’s not the girl I fell in love with.”

And Penn increasingly sounds like someone for whom the romance of movies has faded. He misses Hollywood films that aren’t “just razzle-dazzle, Cirque du Soleil movies,” he says. On Marvel movies, he laments “how much it’s taken up the space and claimed so much time in the careers of so many talented people.” Arguing that today he wouldn’t be allowed to play gay icon Harvey Milk (2008’s “Milk”), Penn recently said that soon only Danish princes will be playing Hamlet.

And Penn’s generally well-regarded directing career (including 1995’s “The Crossing Guard” and 2001’s “The Pledge,” both with Jack Nicholson; and 2007's “Into the Wild”) has lately been rockier. His last film, 2016’s “The Last Face,” with Charlize Theron, flopped, and was loudly booed at its Cannes Film Festival debut. Yet Penn last month returned to Cannes to premiere “Flag Day.”
“I’ve been on such extreme ends on that. It’s like: whatever,” says Penn. “The thing is: I am confident that I know as much — more — about acting than almost any of these critics. And I’m very confident in the performance I’m most concerned about.”

With that, Penn raises his hand and points toward where Dylan is sitting across an otherwise empty hotel bar off Cannes' Croisette. Dylan, 30, is the star of “Flag Day.” She has dabbled before in acting but it’s easily her biggest role yet. In the film, adapted from Jennifer Vogel’s 2005 memoir “Flim-Flam Man: The True Story of My Father’s Counterfeit Life,” she plays an aspiring journalist with a seldom truthful father.

Penn's confidence isn’t misplaced. In “Flag Day,” Dylan is natural, poised and captivating. She looks a veteran, already, which might be expected of the child of Penn and Robin Wright. And those critics? Some have been quite complimentary. Variety said the film “reveals Dylan Penn to be a major actor.”

Just as Penn is withdrawing from movies, his daughter is stepping forward — even if she didn’t immediately seek the spotlight.

“Growing up, being surrounded by actors and being on set, it was really something that didn’t interest me at all,” Dylan says. “I always thought, and still think, my passion lies in working behind the camera. But as soon as I expressed wanting to do that kind of thing, both of my parents said separately: You won’t be a good director if you don’t know what it’s like to be in the actor’s shoes.”

Dylan grants that her dad may be “passing the torch a little bit.” Hopper Jack Penn, her younger brother, also co-stars in “Flag Day.” (The rest of the cast includes Josh Brolin and Regina King. Original songs by Cat Power, Eddie Vedder and Glen Hansard contribute to the score.)

“I have always thought if she wanted to do it, I’d encourage it,” Penn says.

For Dylan, the father-daughter relationship of “Flag Day” — Jennifer tries to help and stabilize her scamming father but also inherits some of his more destructive, conman habits — is a half-reflection of their own bond together.

“She always strived to have this really honest, transparent relationship with her father which she never got it in return,” Dylan says. “I’ve tried to have that with my dad and got it in return.”

Penn has recently been shooting Sam Esmail’s Watergate series for Starz, with Julia Roberts. He's been vocal that vaccinations ought to be required for everyone on set. During the pandemic, Penn's Community Organized Relief Effort non-profit, which he started after the 2010 earthquake to help Haitians, erected testing and vaccination sites, helping dispense millions of shots.

Perhaps those experiences have made Penn only further repelled by anything artificial.

"My tolerance for the contrived is less and less," says Penn.

But working with Dylan came naturally. Talking about her attentive, even disarming presence, he calls her “as uncontrived as it gets.

“I would be sort of taken about by it sometimes, like: ‘Uh, oh. She’s really listening to this. Is she seeing right through this?’" says Penn.
Penn started out younger — he was starring in “Fast Times at Ridgemont High” by the time he was 21. He felt confident from the start in roles that were like him — “young and very shy," as he describes. Staying natural while expanding away from himself, Penn says, has been the journey ever since.
“How do you feel as natural, as free in something where you’re going to the role as in something where you’re bringing the role to you? To varying degrees of success and failure, that’s what the road has been — to find that original unquestioning,” says Penn. “There’s stuff that I see in Dylan that is so unquestioning.”



An Emotional Win for Theaters, Hollywood: ‘Inside Out 2’ Scores Massive $155 Million Opening

 This image released by Disney/Pixar shows, from left, Sadness, voiced by Phyllis Smith, Joy, voiced by Amy Poehler, Disgust, voiced by Liza Lapira, Fear, voiced by Tony Hale and Anger, voiced by Lewis Black, in a scene from "Inside Out 2." (Disney/Pixar via AP)
This image released by Disney/Pixar shows, from left, Sadness, voiced by Phyllis Smith, Joy, voiced by Amy Poehler, Disgust, voiced by Liza Lapira, Fear, voiced by Tony Hale and Anger, voiced by Lewis Black, in a scene from "Inside Out 2." (Disney/Pixar via AP)
TT

An Emotional Win for Theaters, Hollywood: ‘Inside Out 2’ Scores Massive $155 Million Opening

 This image released by Disney/Pixar shows, from left, Sadness, voiced by Phyllis Smith, Joy, voiced by Amy Poehler, Disgust, voiced by Liza Lapira, Fear, voiced by Tony Hale and Anger, voiced by Lewis Black, in a scene from "Inside Out 2." (Disney/Pixar via AP)
This image released by Disney/Pixar shows, from left, Sadness, voiced by Phyllis Smith, Joy, voiced by Amy Poehler, Disgust, voiced by Liza Lapira, Fear, voiced by Tony Hale and Anger, voiced by Lewis Black, in a scene from "Inside Out 2." (Disney/Pixar via AP)

Hollywood’s summer movie anxieties gave way to joy this weekend with the massive debut of Disney and Pixar’s “Inside Out 2.” The animated sequel earned $155 million in ticket sales from 4,440 theaters in the US and Canada, according to studio estimates Sunday.

Not only is it the second-highest opening weekend in Pixar’s nearly 29 years of making films and the second-biggest animated opening ever (behind only the $182.7 million launch of “Incredibles 2” in 2018). It’s also the biggest of 2024, which had not had any films debut over $100 million. With an estimated $140 million from international showings, “Inside Out 2” had a staggering, and record-breaking, $295 million global debut.

The success is significant for Pixar, marking a much-needed return to form for a studio that has had a string of underwhelming launches including “Elemental,” which did eventually become a success, and “Lightyear,” which didn’t. It’s also vitally important for the greater Hollywood ecosystem and the health of theatrical exhibition, which had been running at a 26% deficit before this weekend. “Inside Out 2” marks the biggest opening since “Barbie” launched to $162 million last July.

"This is a monumental weekend for movie theaters," said Paul Dergarabedian, the senior media analyst for Comscore.

Kelsey Mann directed “Inside Out 2,” which picks up with Riley as she turns 13. That means the arrival of new emotions like Anxiety (Maya Hawke), Ennui (Adèle Exarchopoulos), Envy (Ayo Edebiri) and Embarrassment (Paul Walter Hauser) to the mix. Amy Poehler once again lent her voice to Joy in a cast that also includes Tony Hale, Lewis Black and Phyllis Smith as Sadness.

It got glowing reviews from critics (92% on Rotten Tomatoes) and polled audiences who gave it an A CinemaScore, suggesting that this won’t be a first-weekend wonder either. With kids out of school and an open market until “Despicable Me 4” enters the ring over the Fourth of July, “Inside Out 2” is just getting started.

“Inside Out 2” is estimated to have cost around $200 million to produce, which does not account for the millions spent on marketing. Going into the weekend, it was tracking for a debut in the $90 million range, which would have been in line with “Inside Out’s” first weekend in June 2019. Even that would have been considered a terrific achievement, and enough to claim the biggest opening of the year — finally unseating March releases like “Dune: Part Two” and “Godzilla x Kong.”

It got off to a huge start with $13 million from Thursday preview showings, which started at 3 p.m. As the only major release of the weekend, its theatrical footprint was equally impressive playing on 400 IMAX screens, over 900 “premium large format” screens and over 2,500 3D screens.

“The family audience still loves going to the movies,” Dergarabedian said. “As an outside of the home experience, it’s still a relative bargain.”

This recommitment to theatrical comes after Disney sent several Pixar films straight to its streaming service, Disney+, over the pandemic including “Soul,” “Luca” and “Turning Red.” Last month, the New York Times reported that Pixar had decided to return its focus to feature films (and not producing shows for Disney+) and that it had laid off 14% of its workforce (about 175 employees).

“As important as this weekend is for the industry at large, for Pixar this is huge. They’ve been trying to get their groove back since the pandemic,” Dergarabedian said. “Pixar had for decades one of the most impressive box office track records ever. They’ve really come back big.”

Second place went to Sony's “Bad Boys: Ride or Die,” now in its second weekend with $33 million, down only 42% from its opening. In just 12 days, it's already earned over $112 million domestically and $214 million globally. As of Friday, the four-film franchise had crossed the $1 billion mark.

“Bad Boys'” success last weekend was the start of a higher-earning turnaround for the lagging summer movie season. For Hollywood, the summer season, which runs from the first weekend in May through Labor Day, usually represents about 40% of the yearly box office. The deficit is still significant, with ticket sales down 28% for the summer and 24% for the year (and this is still before “Barbenheimer”) but it's progress in a more promising direction nonetheless.

“We're not going to get there overnight,” Dergarabedian said. “But it’s good news for theaters. And we have some big movies on the way.”