Sean Penn Keeps It All In The Family With ‘Flag Day’ At Cannes: The Deadline Q&A

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The son of actor/director Leo Penn and actress Eileen Ryan, Sean Penn will be keeping up the family tradition this year at Cannes when he premieres Flag Day in Competition. Based on her 2004 memoir, the film follows Jennifer Vogel’s personal story of idolizing her bank robber and conman father. Penn directs and plays the dad character, while—in a startling breakout turn—his daughter Dylan stars as Jennifer, and his son Hopper plays her brother. Flag Day comes after Penn dedicated the past year to the distribution of Covid-19 tests and vaccines through CORE (Community Organized Relief Effort), a humanitarian project he founded in 2010 following the Haiti earthquake tragedy. This will be his 11th appearance in Cannes.

DEADLINE: How long had you developed Flag Day, and how long did it take for you to feel that your daughter Dylan had the chops to play Jennifer Vogel, and that she’d share scenes with you?

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SEAN PENN: Originally the script was sent to me by Mark Rylance on behalf of Jez Butterworth. Mark said, “This is something Jez wants you to act in or direct, whatever you’d like to do.” Once I read it, I thought it would be something I might act in. I brought it to Alejandro [González Iñárritu] and he got involved with it a little bit with Jez for a bit of time. And then it sat there.

Bill Horberg was the one who originally initiated it as a producer in the first place, and when he and I talked about directors, we also talked about Dylan. At a certain point, I was seeing her and knew that if I went and played this part, whoever the actress was, I would spend the whole time looking for my daughter’s face in her face. It just seemed that she would own this thing.

We were having some trouble identifying the right director for it, and other projects came up, and Dylan was a little reluctant because she didn’t feel that she had enough experience. I didn’t want to push her, and by that time I could not imagine doing it without her. I told Bill, “Hey, maybe you should move on, I don’t want to slow you down, and I would like to see this movie get made.” And then, it came back around. It’s like we say, every movie’s got its journey. But in the summary of this one, it ended up where we all feel it was supposed to be. I had never, ever thought to direct myself in any movie and I don’t know that I would think to do it again.

Dylan Penn in ‘Flag Day’ - Credit: MGM
Dylan Penn in ‘Flag Day’ - Credit: MGM


DEADLINE: Why not?

PENN: It’s as burdensome as I thought it might be. When I see other people doing it, I say to myself, I don’t know how the hell they do it. I’ve seen people take on large-scale things, like Bradley Cooper and Ben Stiller, and my hat’s off to them. But what I did have here that was so unique, was my daughter. And, like you said, at a time of her having the chops. This [movie is informed by] a life of her coming home from school and telling me stories and bringing forward the characters from school, not in mimicry but in that kind of connected sense where you really felt who that person was, and I think that’s in essence the instincts of an actress. Long before she would have admitted any interest in acting, I just always thought she was an actress. But it wasn’t until we got to set that there were some major WTF moments on the kind of truth machine that she can be.

DEADLINE: You started acting earlier. She’s 30. As a parent who has seen all sides of a business that can chew up young people, how did you feel about your kids acting?

PENN: Good question. Let me take you to a scene [in the movie], between her and Katheryn Winnick when they’re in the kitchen.

DEADLINE: There’s a physical confrontation between them in that scene.

PENN: I say this jokingly, but I felt it in a sense that putting her through take after take of that scene, I should probably call Child Protective Services on myself. Look, the business can beat any of us up, it beats us all up at some time. It rises us up, it beats us up, we rise ourselves up, we beat ourselves up. The tough part to me of acting, is encouraging them in a profession where you are a canary in a coal mine on emotional things, and over some years that can really take its own toll if somebody isn’t finding a real way to contextualize it to themselves, and be able to not take your work home too much and all that basic stuff. Like any craftsperson, any professional that deals in the world of intense emotion needs to find a healthy place to put that. If I have a concern for my kids, it’s in that area more than the business at large. I’ll encourage them on any path they want to take, and at the moment film is for both of my kids a great interest, and not only as actors. I know my daughter’s very interested in writing to direct herself, you know?

DEADLINE: As a filmmaker, how much of an advantage is it also being an actor?

PENN: I always feel that when I’ve written a script, it’s the writer that I think can be an advantage in talking to actors, because as a writer you have done a version of it in your imagination as you’re typing. You’re hearing the music of it. So long as you’re tailoring the way that you talk to somebody, I do think the advantage comes from having been inside the piece, which is the writer part of it. That I’m an actor, I don’t think that gives me a great advantage, because actors are all so different in how they approach things. If I were directing me, yes, it’s an advantage, but in directing others I think I go to the writing side. And with any script that I have not written, like Flag Day, I do a couple of serious passes, adjustments on it, so that by the time I’m done I try to convince myself I wrote it, and with Jez Butterworth’s writing that’s how I praise myself. But it’s really that I’ve found enough of my music so that it becomes the same thing.

DEADLINE: What were the biggest challenges of asserting yourself as the director, as the co-star, and Dylan’s father on set?

PENN: I’m going to tell you, there were challenges. She’s a strong, young woman and I’m her dad, and so, yeah, there were challenges sometimes. But I was so overwhelmed by her. Of course, the amount of pride I got to experience on a daily basis, whatever day she may have had… Let me put it this way, I was working with a director recently who said that there are only three thoughts an actor has after doing a take and the director’s approaching them with notes. It’s, fuck you, I suck, and what was that note again? But at the end of that day, I’m seeing her give that great performance, and I do think I was able to be helpful a lot of times, but also a lot of times she had such an immediate instinct. She’s a very intuitive person, and therefore an intuitive actress.

But it was thrilling, you know, the end of those days, having collected the footage of the things she was putting out there. Really thrilling.

DEADLINE: This is your 11th film premiering at Cannes. You won the best actor prize, and you headed the 2008 jury. How important is it to be part of this festival, which signals the reopening of the theatrical movie business that basically got crushed by streaming and the pandemic?

PENN: I wouldn’t say that Cannes is the only film festival that represents what I’m going to say, but none represent it better. Initially it was Gilles Jacob and now Thierry Frémaux. They are cellular believers, in love with cinema on a big screen, theatrical cinema, versus streaming and what seems to be threatened by that, especially movies that are thoughtful, in some way or character driven. Cannes is just a big celebration of that. When you go there with a film as an actor or director, your schedule doesn’t allow you to participate in the festival at large. The very best time I ever had at Cannes came when I was on the jury, having the experience of this swarm of international cinema, great cinema. The imagination that comes through the prism that isn’t just American, because we’re assuming it’s so monocultural in our thinking, and to find out, my god, there are really great filmmakers in the Philippines, you know? These things sound so exciting, and having had that, and knowing that that’s what’s going on under the seat of whatever film you’re going to, and that you’re a part of that with those other filmmakers, that’s really exciting. This year, there are some really visionary directors with films. It seems on the surface anyway, like Thierry Frémaux put together something pretty thrilling. I think, especially for the films that are lucky enough to show at the Palais there, that’s the way you want a movie to be seen.

<img class="size-medium wp-image-1234789436" src="; alt=" - Credit: Richard Shotwell/Invision/AP" width="200" height="300" srcset=" 1667w,,150 100w,,300 200w,,1024 683w,,1536 1024w,,2048 1366w,,60 40w,,468 312w,,225 150w,,165 110w,,428 285w,,240 160w,,480 320w,,960 640w,,600 400w,,1200 800w,,768 512w,,1920 1280w" sizes="(max-width: 200px) 100vw, 200px" />Richard Shotwell/Invision/AP

DEADLINE: You seem like a pretty tough guy, but can we anticipate a little tearing up as you share the Flag Day red carpet at Cannes with your daughter and son?

PENN: There are no guarantees one way or the other. It’s a big deal for me, a big deal. It’s funny. We had a rehearsal because I went once with them as my guests, but this is different with both of them in the movie, and with her leading the thing, yeah, it’s pretty exciting. I’m very excited for her. Where the future may not hold for any of us a lot of opportunities for a film like this to be presented as a movie in the theaters, just to know that she’ll have had this experience. Because people might not like a movie, and all that stuff, but if you go in there believing in the thing, and you go in there on your own terms, then there’s a certain magic to that, no matter what happens.

DEADLINE: Your dad was an actor and a filmmaker, your mom was an actress. What kind of influence were they on you?

PENN: It’s hard to articulate. I grew up in a house where, working in theatre, working in film, drama was held in high esteem. It didn’t occur to me that I was going to want to get involved in it until I was in my late teens, in the senior year of high school. I had thought I wanted to be a lawyer and I got involved in making Super 8 movies and got the bug. Once I got into it, it was at that age where you’re not associating it with your parents until later, so I never felt the direct connection until I was probably in my mid-20s. Although, when I started to work in theatre, my parents would come. Ultimately it became quite encouraging, but my mother, the first thing that she saw me in, she said, “You have got to go to university, you got to have something to fall back on. That was terrible!” But ultimately became quite encouraging.

And Dad was a filmmaker. It’s interesting. I just ordered and got a DVD of the first feature film that he made in 1965, a movie called A Man Called Adam. I wanted to kick myself. I had seen it at some point where I wasn’t paying attention to what directors were doing. And I look at it now and it’s… if you wanted to shoot that movie today, you’d be lucky to get to make those choices. It’s an extraordinary movie and… I wish I could sit down and talk through that movie with him, shot for shot. Never did do that, and I wish I had.

DEADLINE: You were among the young cast of Taps, along with fast risers like Tim Hutton and Tom Cruise. Were you competitive?

PENN: Tom was so, what’s the word, sincere a guy, that I overlooked his talent. I will tell you that I loved him and thought he had no chance in this business. Because he was just so nice, and seemingly naive at the time. Of course, he’s become this force as a professional. As good as he was in Taps, I totally underestimated his talent, the things that came later which are really extraordinary, and he’s really a machine.

DEADLINE: You mentioned your mom saying you’d better go to university. How much harder were you on your kids about finishing school than your parents were on you?

PENN: I think I was tougher on them, but they needed… It was different, and their personalities are so different, so the expectation was high. Hopper was more like me as a student. You know, much more interested in his childhood than his studies. Dylan was much more tough on herself in terms of all that. She went to USC for a little while, and then one night just called and said, “Dad, this is not for me.” And I said OK, and then she started getting involved in writing a lot of things and looking at film. But you know, I regret my own missing out on that. I remember touring universities with her thinking, wow. But you need to be ready and hungry to learn and I didn’t get hungry to learn at that age. I got it a little later.

DEADLINE: Your dad flew missions in World War II, and afterward got blacklisted as an actor for attending meetings in support of unions and refusing to name names of others who attended, before the House Un-American Activities Committee witch hunt. I defy anyone who watches Citizen Pennto not be gobsmacked by the sustained accomplishments in post-earthquake Haiti by you and your relief organization. What is it inside of you that makes you plunge into these seemingly impossible humanitarian rescue missions, where most of us write a check? How much of your dad is in you to lead these efforts?

PENN: In one sense, I’d answer the question saying a lot, a lot. I’m in a daily conversation with my dad, because he was a hero to all of us. And I’m not talking about the war stuff, I mean, just as a man. He was such a good, kind, decent, talented, smart guy, and very generous with people and very supportive of people. And so, you know, given that he was that, what he was doing in his war fighting experience had a seven-mission life expectancy and after that it was all volunteer. And he broke the record at 37 missions, was shot down twice getting the aircraft back over allied lines before jumping out. And so having done that with an incredible, real deep connection to, and an appreciation of Americanism, of what that dream could be, patriotism… To come back and have the country you fought and risked your life for, tell you, you can’t work anymore. I think he went through about five years where he wasn’t able to work under the blacklist. He never spoke about that with bitterness. He always wrote it off as growing pains of the country. That part of him I did not inherit. I’d have been one pissed off MF’er, and it does piss me off to think about that stuff as it applies to my own father, as it applies to people even today in so many ways, new and viral ways and so on. It’s hard to be a human today, which is one of the things that’s great about filmmaking. It’s the place where we can talk about it, literally, directly, or just by expressing something.

DEADLINE: It sounds like your father stoically bore the burden of what happened to him. How did observing the scars shape you?

PENN: I don’t know that what I observed were scars, because the person who took care of business during that time was my mother. She could work. He got a job in a plastics factory for a time, but she was the reason they ended up coming out to California, and because there was a lot of television work happening at the time, she was able to support the family with Twilight Zone guest starring parts, or Bonanza or whatever.

I’m a beneficiary of parents who loved each other, and I think more than I saw the scars of what had happened, for the most part before I was born, I saw a relationship that had been strengthened by it. I think more than anything, it’s not so much my dad’s activism that would have played a role in this, it’s that I had it so damn good that it’s just too obvious, and it just kills you when you see how difficult so many people have it.

And then it’s just the luxury of being able to say, in the case of the things I’ve gotten myself involved in, ‘Let’s start with, I can afford a plane ticket,’ stuff like that. And then, being a high-profile person, you’re a magnet to good and bad people, but you’re able to cast your team and things come your way much more easily, including in a place like Haiti or whatever it is. So, it’s not all stuff that I can answer because it truly is not all stuff that I own specifically. I lucked into a lot of it.

DEADLINE: I’ve had the pleasure personally of watching you evolve as an artist, but I’ve also watched you go from the paparazzi-punching bad boy, as you were once called, to this statesman who’s done so much humanitarian work. What changed your approach?

PENN: It’s a complicated question because as [Citizen Penn director] Don Hardy exposed very well, I can get really frustrated with the hat-in-the-hand part of this, and yet, these are like so many things. I mean there are certainly a lot of times, and it makes for good cinema, when your rage is forward, or it’s like, “Get this!” and you’re screaming. I do think that it becomes increasingly apparent naturally for all of us to be in pursuit of a more compassionate demeanor in whatever you’re doing. And then that much moreso given where our country is right now, that just fighting or just demanding—just the pretention of your own self-righteousness being the valid one—it’s gotten to a point of diminishing returns.

So, I’m going to call the way that a lot of things did happen out of certain aggressions of mine over the years, that there are just diminishing returns on that way of approaching it, and maybe it’s just a younger man’s game in that way.

DEADLINE: There was an example where that willingness to go outside the box paid off in a profound way. We saw you criticized on TV for your relationship with the late Venezuelan President, Hugo Chávez, with whom the U.S. government always had a strained relationship. When you heard that amputations of crushed limbs with rudimentary hardware tools were going on without anesthesia after the earthquake in Haiti, you got morphine and other anesthetics by simply asking Chavez. That was unbelievable.

PENN: Well, I had… You know, it was a kind of a safe thing, because about six days before the earthquake, Madonna had sent me her documentary on Malawi, and I watched it here at the house and that was my introduction to Paul Farmer, the founder of Partners in Health, which works significantly in Haiti, but they work around the world. Paul is an extraordinary Harvard doctor who built an incredible NGO in Haiti 30 years before I ever got there. He had an interview in that documentary, and I was so impressed with him, I looked him up and saw who he was.

Haiti had been in my thoughts the week that the earthquake happened, and when it happened and I thought, OK, do something there, I’ll bet Paul Farmer’s there. I was able, through her, to get a number for him, and sure enough he was there. I asked him what was needed and he told me: 350,000 vials of morphine. It’s always been my joke, an actor in Hollywood knows where to find narcotics, but most don’t know where to find bulk narcotics. Things are different in a country like Venezuela. No one in politics, from a president down, is going to overrule their Minister of Health and say, “Hey, this person who is not credentialed to have or get near morphine, we’re going to give it to them.”

We didn’t bring it from the United States, it was brought in from Venezuela to the Venezuelan Embassy on a military transport. We picked it up, and then started distributing it.

DEADLINE: What is the lesson in not shutting off dialogue with leaders in countries who are on the outs with the U.S. government?

PENN: Well, this was a very particular thing, and that’s a longer conversation. But certainly, in general, I am someone in favor of dialogue.

Some people are socially, economically strapped away from traveling. Some people have a lack of curiosity to travel, and biases. But I find the people on the political right or people on the political left and anywhere in between, any that have worked in Foreign Service really know the world, and have looked at our country through the eyes of other cultures. There’s a lot more tolerance and a lot more belief in dialogue in those people.

I have great friends who are extremely conservative, and have led long lives in public service. We have so much in common with our perception of conversations, including with these bogeymen, be that Fidel Castro or Hugo Chávez or Evo Morales. It’s not that it is an apologist conversation, but it’s a much more nuanced conversation to have.

DEADLINE: The U.S. has turned a corner for the better lately, but the pandemic continues to rage in poorer countries. What’s next for CORE in that regard?

PENN: So, we are in the favelas of Brazil now, doing vaccination clinics. We are in India. And we are in a lot of the behind-the-scenes advocacy for distribution. We are very concerned to get vaccines to Haiti, which is having a spike. It dodged the bullet for a while, in part because it had a pre-Covid lack of tourism, and once Covid happened, you didn’t have a lot of influx of people from the outside coming in. But now it’s becoming a bigger issue, and so we’re trying very hard.

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In all of these things, CORE can’t be… the procurement of morphine at the earthquake is a very unique situation. There was a kind of… I don’t want to say lawlessness. There was that also, but there was an understanding that a lot of things had to be waived and looked at very differently, and also, because the United States military had been given control of the ports by the Haitian government. So, international law, everything applied very differently, at least I think so, unless somebody knocks on my door for doing these interviews. But CORE can’t bring this stuff into the country, not without a lot of officiation, and there’s a cold chain.

What we do is advocate for its delivery, and then be part of working with the Haitian Ministry of Health in its implementation. Bringing together our clinicians to be able to give the injections. That’s what we’re up to and I think we will stay in that game in those territories and then expand as possible, until we are whatever small part of seeing this thing end, worldwide.

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