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Great Conversations: Sean Penn

05/07/2015 03:28 pm ET | Updated May 07, 2016

I interviewed Sean Penn in the piano bar of the Hotel Bel-Air in November 2001. The tragedy of 9/11 still hung in the air, casting a heaviness on everything. I approached the proceedings with a certain amount of trepidation, given Penn's volatile relationship with certain members of the press in the past. Those concerns were immediately put to rest the minute we shook hands. Full disclosure, Penn and my then-wife, an actress with whom he'd worked some years before, were good friends during the 1980s. Penn's publicist at the time, Carol Marshall, informed him of this, which might have put Penn more at ease. That said, what followed was another of the great conversations I've been lucky enough to have been part of.

I AM SEAN:
Sean Penn is the best American actor of his generation for one reason: He remains undeniably, defiantly, himself.

The year was 1983. Sean Penn's glowering mug graced the cover of Rolling Stone magazine, emblazoned with the label: "Bad Boy Sean Penn: The Next James Dean." Okay, there it was in black and white. Sean was a boy. He was bad. And he was heir apparent to the throne of the posthumous boy king of teen angst, Jimmy Dean. Rolling Stone said so. Therefore, it must be thus.

They say the worst fires in the world all started with one tiny spark, and that could well have been the spark that ignited the media frenzy that labeled, berated and often attacked Sean Penn during the paparazzi heyday of the 1980's, eclipsing a talent that, unlike James Dean's, has had the opportunity to grow, be seen and survive since that unfortunate decade ended.

Sean Justin Penn was born into a show business family on August 17, 1960 in Burbank. Father Leo Penn, who succumbed to cancer in 1998, was a former actor and blacklist survivor who had gone on to become the top television director of his generation. Mother Eileen Ryan was also an actress with an impressive list of stage, screen and TV credits to her name. Spending his formative years in Malibu with older sibling Michael (now a successful composer/musician) and younger brother Chris (himself a well-known actor), Penn discovered acting towards the end of high school, acting in and directing super 8 movies with neighbor and classmate Emilio Estevez.

Although he had initially intended to become an attorney, Penn decided to forgo law school and college altogether, jumping headfirst into acting. Penn made the move to New York in search of stage work. Not long after hitting the Big Apple, Penn landed the lead in a production that wound up on Broadway. It was this high-profile exposure that landed Penn his first film, Taps (1981), which also introduced Tom Cruise and Giancarlo Espisito. Stardom and icon status were reserved for one year later, however, when Fast Times at Ridgemont High filled every neighborhood multiplex during the summer of 1982. Penn's now-legendary turn as ultimate surfer dude Jeff Spicoli, whose catch phrases "Hey bud, let's party," and "Awesome, totally awesome!" immediately became part of pop culture slang, turned him into a household name overnight.

Penn's next film, Bad Boys (1983), had critics and public alike calling the 23 year-old the finest actor of his generation, with his portrait of a Chicago street tough who lands in a brutal juvenile prison, the polar opposite of the goofy, good-natured Spicoli. Although not all his films were box office champs, Penn's work in a diverse series of intelligent, serious works, were clear indication that Sean Penn was about the work, not about the spotlight: the love struck kid bound for WW II in Racing With the Moon (1984); the drug addicted turncoat in The Falcon and the Snowman (1984); the son who refuses to follow in his murderous father's footsteps in At Close Range (1986); the tough L.A. street cop in Dennis Hopper's Colors (1988); the undercover cop in a crisis of conscience in State of Grace (1990); the overzealous attorney with a taste for danger in Carlito's Way (1993); the death row inmate struggling to make peace with himself in Tim Robbins' Dead Man Walking (1995, Penn's first Oscar nomination); and most recently as the tough-minded but compassionate sergeant in Terence Malick's The Thin Red Line (1998), and the loathsome jazz guitarist in Woody Allen's Sweet and Lowdown (1999, Penn's second Oscar nomination).

While the comparisons to James Dean, Brando, and Nicholson still endure, Sean Penn's talent, style and persona seem to embody an earlier breed of old school actor and raconteur: Robert Mitchum. Spencer Tracy. Lee Marvin. All of these giants of understatement might have shared a mantra that would have gone something like this: "First and foremost, I'm myself. I love my work. I bust my ass to do the best work I can. I'm not interested in being liked. I'm not interested in being pretty, or polite, nor do I care if I offend on occasion. If you don't like me, that's your privilege. If you get in my way or provoke me, we're going to have a problem. Is there any of the preceding which you didn't understand?" Old-world honesty combined with timeless talent has kept Sean Penn and his work fresh and interesting, while many of his generation have seemed happy to relegate themselves as packaged pieces of product instead of actors. Long after the former have vanished from memory, Sean Penn's work will undoubtedly leave a legacy that survives.

Penn's latest is the New Line release I Am Sam, in which he plays a mentally handicapped man caught up in a legal custody battle for his young daughter. Michelle Pfeiffer co-stars as the high-powered attorney who reluctantly represents Penn's character, and finds salvation in the process. Both leads give Oscar-caliber performances in this powerful film, which also boasts a stellar turn by newcomer Dakota Fanning as Lucy, the daughter in question.

Sean Penn sat down recently to discuss his work, the genius of Jack Nicholson, and the liberation of being one's self.

It's always struck me that when an actor portrays a character with a physical or mental handicap that there's a fine line between character and caricature. Is that a difficult line to tread?

Sean Penn: Well, you're never going to cross that line if you're part of an acting process that isn't based on caricature in the first place. I think any performance can be caricature in terms of the criticism if that's what it is. I've always looked on acting as this: you build a cage based on your sense of the truth and your sense of the aspects of the character that need to tell the story. If you've done your job right, which I've had varying degrees of success doing at different times in my life, if you've done your job right, then you're able to function very freely within that cage. So I think if you're editing yourself, you're going to fall, and that's what comes to mind when you use the word "caricature," to me it says you're avoiding something.

Did you have a chance to observe people who had the same handicaps that your character had?

Yeah, but I think what you find is what you're going after, since there's such a broad spectrum of conditions, many of which can overlap one another, what becomes most important is finding the personality of the character, like with any character. So I was trying to do that. Then you absorb things based on observation, or try to.

One thing that the film captured beautifully is how many so-called "mentally challenged" people are much sweeter and more "human" than supposedly "normal" human beings.

Absolutely. You can't beat innocence as a sort of wellspring for kindness. Little kids have that, as well. I think that's most of what we're about at our best anyway, so it becomes a very human exchange.

Your scenes with Michelle Pfeiffer just cooked. The two of you really played off each other beautifully.

She's just so great. Michelle is one of those actors who makes coming to the set every day a pleasure. She's very honest, and working with honesty is what it's all about.

Let's talk about your background. Your parents both began as highly regarded actors and your father went on to become the top television director of his generation. Obviously a lot of that rubbed off on all three Penn boys. Did you "go to the office," so to speak, with your dad a lot growing up?

I did, although not at a period of time when I thought I was going to go into that line of work. But from the time I was a little kid, I would spend a lot of time on sets, just watching.

What did you learn from your dad as a director?

Well it's interesting, it's hard to put into words because at a certain point everything you learn from a person or an experience all blends together. (pause) He was a very good storyteller. He talked a bit about directing with me, and looking back I wish I'd talked to him more about it. But again, you absorb things as opposed to learn things. Also, there was a general respect for drama and theater that he had which was definitely passed on to me.

Sean and Leo Penn.

Your dad was also a victim of the Blacklist. Was that something that he ever recovered from emotionally?

Emotionally, oh yeah. Guys like my dad came back (from WW II) after risking their lives for this country, and then they weren't able to work in the country they risked their lives for. He was a patriot. I think there were some individuals that he might have harbored some vague resentment toward, based on their cowardice at the time. But he was really someone who was very comfortable in his own skin.

How did the knowledge of what had happened to him inform you and your brothers growing up?

Again I don't know. I wish I could speak to it better. I think there's an acceptable level of sacrifice, or rather that sacrifice is an acceptable thing, and we grew up knowing that. He sacrificed for his beliefs, but in the end, he was very fulfilled.

You spent most of your formative years in Malibu, where your next-door neighbors included Martin Sheen and his family (Charlie Sheen, Emilio Estevez) and the Lowes (Rob and Chad).

I lived in Malibu from '71 to '78. I knew Emilio. Charlie was a friend of my younger brother, Chris. But I didn't know the Lowes. Most of those guys were 3-5 years younger than me.

When did you know you wanted to be an actor?

It was around the time I got to know Emilio, towards the end of high school. We started making super 8 movies together.

So it sounds like you wanted to direct originally.

That's what I wanted to do and was doing, but there was a kind of absence of actors. (laughs) We'd shoot at night and people would, you know, go home, do their homework, so I started to act in these little films as well. I sort of wound up becoming obsessed with the whole process (of acting). So I went to acting school and joined a repertory company right out of high school.

Actor Pat Hingle.

You were also an assistant for Pat Hingle, a great actor, at this point.

Yeah, Pat was great. Great guy, and a wonderful actor. I was working at Lonnie Chapman's repertory company and there were doing a production of "Toys in the Attic" and Pat was directing it. I got to be his assistant director. Pat was of my dad's generation. They'd worked together before.

After high school you skipped college and went right into acting.

Yeah, what happened was, I stayed here in L.A. for a while and was doing a lot of equity waiver theater. But I wasn't making a living. So I went to New York. When I got to New York, I did get a play. It was supposed to be off-off-Broadway, then it got cancelled. Then it was on again. Then it got cancelled again. Then the only theater available was a Broadway house. So they got some investors and we launched it there. So that was just kind of a lucky break where I was able to do something and be seen in something. That led to my getting my first movie, Taps.

Both Taps (which co-starred Timothy Hutton, Tom Cruise, Giancarlo Esposito) and Fast Times (Jennifer Jason Leigh, Eric Stoltz, Nicolas Cage, Anthony Edwards, Forest Whitaker, Phoebe Cates) were sort of the American Graffitis of the 80's with all the new, young talent they introduced.

Yeah, it was an interesting time. From our point of view, there really weren't a lot of movies being made with guys our age, until Tim Hutton did Ordinary People, won the Academy Award, and all that, and then all of the sudden movies were being made about young people again. Prior to that, there were guys like Richard Gere and John Travolta. So suddenly, there was employment to be had. (laughs)

Was Jeff Spicoli like a lot of the guys you'd grown up with in Malibu?

Oh yeah, and a big part of the excitement of playing that part is that I hadn't seen any of those guys in a movie before. I felt as I was reading Cameron Crowe's book, "Finally, they got one of these guys!" (laughs) It's just as American a character as a New York cabbie.

Did you choose the part in Bad Boys as your next film largely because the part of Mick was so diametrically opposed to that of Spicoli in Fast Times, sort of like what Dustin Hoffman did by playing Ratso Rizzo in Midnight Cowboy immediately after The Graduate, so he'd avoid type-casting?

No. I'll tell you something: I've never been a careerist. In fact, I might even be an anti-careerist. The first rule of Italian driving is you pull the rearview mirror off, because what's behind you doesn't matter. It doesn't matter if I'm doing something that's similar. If I haven't moved on humanly, there's no moving on anyway. It's about doing things that are interesting to you at the moment.

After Bad Boys, Rolling Stone put you on its cover and tried to label you as "The Next James Dean," which began almost a decade of the press trying to label, package and sometimes even harass you. I always thought it was admirable that you rebelled against being put in any sort of category.

I never felt I was rebelling against it. And it's something that continues to this day. I don't understand most of what's said, to tell you the truth, about me or about the movie business in general. I feel like what I observe is not what I read about most of the time. So I felt a kind of disregard for what was said at that time. Later, it became a little more intrusive. It was one thing when people are talking about you this way in the press and you're reading it, but it's another when judges are reading from the bench things that have been written about you to validate the sentence they're about to hand down! (laughs) So that's when I became a little more annoyed. It's a world that doesn't suffer the complexity that any of us have, the world of the press. Whether you're bright or not isn't the point, and so they want to break everything down in a simple, simple way, and the second they do that, it is something that people can fall victim to. But, I'm still standing.

Right, but what I'm saying is that in face of it all, you've stayed yourself, whereas a lot of other actors of your generation have fallen into niches that others have carved for them.

I think that's true of every period, and in every business. Very few people know who they are in the first place. So once they start to be given a character to play, they'll take it. I think this is less a conversation about Hollywood than it is about parenting. (laughs) I had very good parents. Even as a young person, I felt pretty sure about who I was. Sure I made tons of mistakes, but I was always very clear about who I was.

That's the greatest gift you can give your kids, isn't it?

Yeah, it's really the only gift, other than to let them know they're loved. The rest they tend to build themselves.

The Falcon and the Snowman was a terrific movie by one of my favorite directors, John Schlesigner. What was it like working with him?

Difficult. I too had been an enormous fan of his. He made some great movies, no question, but we had a difficult time. Today, it would be unfair to John to try and articulate it the way I remember it, because I remember it with those eyes. The arguments that he continues to make on his side are those movies he made prior to that. We never found the center where we could talk about the picture. He made the movie very differently from what I had in my mind, so I always felt like I had to protect the character I was playing from the director. That's not the most productive way to be working. You want to protect the character, but you want the director to be on your side while you're doing so.

Penn with Dennis Hopper on the set of "Colors."

In Colors you worked with Dennis Hopper as your director. Do you find that when you work with someone like Hopper, or Tim Robbins (who helmed Dead Man Walking), both of whom are actors that also direct, that they're informed about the whole process differently than someone who just directs?

Yes. And in the case of Dennis, he's just a very creative person on every level. So you're on a creative ride when you're with Dennis. With Tim, he'd written (Dead Man Walking) also, and I think it's even a more significant similarity (in terms of the process) for an actor to be working with a writer-director, as opposed to an actor working with an actor-director. The writer has taken all the steps of the character that you take as an actor. Just to be an actor-director doesn't necessarily make the process better for the actor you're dealing with. In Dennis' case, he transcended that and his force is just a totally different, wonderful thing. But with a writer-director, that person has been sitting in a room alone, going through all those same steps of the character that you're going to be taking.

For you when it comes to writing, do you find that's the most creative process versus directing and acting? Or is it a combination of all three?

Yeah, I think writing, because it's on your own time. There's something about picking your moments of sharpness versus having your moments picked for you. When you're a director you're not going to think 'Okay, we'll start shooting when I feel the "oomph" kick in!' (laughs) You can't, or the money starts clickin'. Alone when you're writing, yeah, that's the place.

Do you tend to work quickly when you write?

I usually think about the story for a long time, then write fast.

You made your directing debut with The Indian Runner in 1991. What was it like for you finally stepping behind the camera?

I had a story I really wanted to tell so it was very easy, in a way. On the other hand, your first day on the set, you see all these trucks, all these people, and you say 'Where are the adults? Who are they actually entrusting all this money to, me?! Uh-oh!' (laughs) But I was pretty clear about the story I wanted to tell, so I'd say it was the first best experience I ever had.

All three of your films as a director are very compelling works. You seem to have a filmmaking sensibility that's much more European than American.

I've heard that said. I, of course, take great pride in the Americanism of those pictures, but not in the American cinema (which they inhabit). I think that the American cinema went away, and is still away, for a while. My biggest inspiration isn't European cinema, it's the American cinema of the 70's. But I think in the void of that, I've probably been influenced in some ways by some European cinema, but my primary influence would be that decade when I was between 10 and 20 years old. Every weekend I went to the movies, it was an event. An event that's still remembered today.

So who specifically are some of your directing influences?

Terry Malick, Hal Ashby, John Cassavetes, Francis Coppola, Jerry Schatzberg, William Friedkin is a very visceral filmmaker...

His film Sorcerer is one of my favorites.

Great movie! In fact, Sorcerer established, I think, a visual sense that has been co-opted by advertising and every other form of media. It was just so dynamic, and one of the very, very influential movies of the 70's, and still is today.

In Carlito's Way you got to work with two giants of their craft: Brian De Palma and Al Pacino.

I had worked with Brian before and got on just fine, although we had tougher time on that one. Our sensibilities were just different. Al I loved working with. He's one of those sort of bulletproof actors. There's nothing in his game plan that will be fucked up by anything you do. He will go wherever you want to go. Working with him balanced that whole experience out.

Jack Nicholson is your favorite actor to work with as a director, obviously. Tell us about Jack.

I love this guy, in every way. (laughs) Just a great fuckin' guy. Brilliant all the way around. He's just the biggest blessing I've ever come across in the business. Just a gift. Collaborating with him becomes seamless after a point. We start early, a year early, talk it out, layer it out. I'll go back to the drawing board on the script, hammer it out. He'll come up with ideas and we'll incorporate them. By the time we get going, it's just effortless.

As a filmmaker, do you think it's good to have bad examples along with good ones?

Every example is a valuable one. And sometimes I'll work with a director just to be around that director. Oliver Stone was one of those. I think he's very talented and I wanted to see how he came to his decisions. Terry Malick, who's one of my favorite discussion topics, is another. I was as interested in being in that picture as I was in being an observer on the set, getting a front row seat. Terry is just an elegant gentleman and a wonderful poet.

Does he work very organically? His films have that quality.

I think he writes his movies three times: he writes the script, re-writes on the set, then re-writes in the editing room. So you don't know necessarily what movie you're doing. (laughs) So it was a very different process for me, sort of yielding to him that way. It was almost like acting in neutral. You'd let Terry decide on the character's music, and whatever else he does. You don't invent too many specifics in a film of his. That was my experience, anyway. It was just better to let Terry determine the ebb and flow of character, and the whole process took several weeks while we discovered how to do that. I wish Terry would make more films. He was going to start on another one, but it would have meant filming in an area that's become a real hot zone, post-September 11.

Regarding September 11, do you think that the world has been shaken both physically and culturally to the extent that it will affect the kinds of films that are made?

I hope so. I think we all have to figure out what's relevant. And for the audiences, I think they've suffered a great discomfort and they've been part of a country that, to the point of a disease, has needed and been addicted to comfort. And the level of this discomfort, tragedy, and sadness has, I hope, raised the bar so that instead of avoiding thoughtful things, perhaps they will seek them out.

Do you think that the basic cyclic nature of things will also take affect?

Of course. It's all cyclical. Those films of the 70's that we've discussed, that sort of movement will come back again. It has to.

In a way it already has, with independent film.

Yeah, to an extent, although very few so-called "independent films" really have reached the heights of those that we've discussed, I think. A lot of times those films wind up becoming their own sort of complex. I mean, what is an "independent film," but a film by an independently minded filmmaker? It could be a $100 million film or a $10 film. A lot of the so-called "independents" I think are just as bad as everything else. But once in a while one comes through that becomes sort of a representation of a good movie, and you thank God for it. Maybe the acting is there, and the story is there, but they just didn't get enough money to make it on the level that it needed to be made. I mean, you could make Cuckoo's Nest today if you had those actors and that script. Let's say in today's world it would cost $45 million to do. If you only had $5 million, sure you could do it. But it would only be a representation of what we saw. It wouldn't be the same. And I think that's what a lot of independent films wind up as, representations. They're charcoals, instead of oils.

Tell us about Woody Allen.

Love him. Flat out, love him. He writes great, period. From there, you have a guy who is unafraid to be absolutely direct and just tell you that something flat out sucks! (laughs) I like it direct! It's liberating. Then I, as the actor can say, 'Okay, let's throw that out and try this.' It's much less taxing. Woody is a very civil moviemaker in that you're not there all fucking day. He doesn't do a lot of coverage and his films aren't really dependent on that.

Any advice for first-time directors?

Always consider the possibility that everyone else is wrong. (laughs) Whether it's on a set, whether it's talking about the script with financiers and they want to change something...if you have an instinct, try to hold on to that instinct about why you wanted to make the piece in the first place. You won't always be right, but there's a chance you will be most of the time.