He walks haltingly, with a cane, grimacing occasionally, and there’s no denying that the passage of the last twenty years has left its imprint not just in his features but in his demeanor. Still, it has to be said: At 36, Leonardo DiCaprio looks pretty damn good. He is at the moment, however, a man in pain. Specifically, his foot hurts. Thanks to a day-old basketball injury (“No more basketball for a long time,” he says with twilight-of-the-jock stoicism), he’s hobbling after four hours of running around. DiCaprio does the man-in-pain thing with exceptional grace. He always has. His career arc has been that of an actor determined not to be defined by a certain emblematic romantic role. Instead, he’s put together a body of work that adds up to an ongoing portrait of the male psyche in various states of disintegration and despair, from the weak (Revolutionary Road), to the bereft (Inception), to the utterly mad (Shutter Island).

For a movie star of his generation who also happens to be Hollywood’s most highly compensated male actor, that constitutes a remarkable first act—all the more so because it’s clear that what really interests DiCaprio are acts two and three. Which may be what brought him together, finally, with Clint Eastwood, the greatest late starter in the history of the movies. When Eastwood, now a hale and vigorous 81, was DiCaprio’s age, he was a small-screen footnote, just coming off the canceled cowboy series Rawhide. He’d made a few Italian Westerns with Sergio Leone while on hiatus, and he wondered if they’d ever get released in the U.S. Over the four decades that followed, he remade himself first into a movie star, then into a director, then into a world-class filmmaker who, astonishingly, did not receive the first of his ten Oscar nominations until he was past 60.

In J. Edgar, the thirty-second film Eastwood has directed, the two men plumb the psyche of J. Edgar Hoover (played by DiCaprio), exploring the life and times of the fearsome patriarch of the FBI in alternating time frames that depict Hoover making his name as a crime-fighter in the 1920s, contending with the Lindbergh kidnapping in 1932, becoming a morally questionable anti-Communist in the 1940s, and fighting to hold onto his empire during the Johnson and Nixon administrations. The script, by Milk screenwriter Dustin Lance Black, is, among other things, the story of how a once great man can rot—a subject in sync with both Eastwood’s taste for depicting the dark side of power and DiCaprio’s for playing the fear and vulnerability that often lies beneath it.

This latest partnership makes sense for DiCaprio, an actor with an appetite for working with auteurs (see his four-film partnership with Martin Scorsese). He comes into Eastwood’s bungalow, which is situated in the middle of the unofficial heavy-hitters section of Warner Bros.’ Burbank lot (Watchmen director and current Superman custodian Zack Snyder is right over the hedge; Inception‘s Christopher Nolan, DiCaprio’s last director, is just down the footpath), and settles onto a couch, elevating his swollen eggplant-colored foot on a coffee table. There’s something undeniably exhilarating about seeing these two independent, no-bullshit stars from very different eras of Hollywood not only in the same room, but finally joining in a working relationship. What took them so long?

GQ: Had the two of you ever come close to working together before?
Clint Eastwood: On another project that never came to fruition. The thing I’ve always admired about Leo is that he’s willing to extend himself. He could easily, at his stage, be doing some of these comic-book movies that are making a tremendous amount of dough, but he wants to be an actor who’s finding new things to hurdle. I saw a little bit of myself, what I used to have.

GQ: [To Eastwood] You’ve made movies before J. Edgar about the uses and misuses of justice, from Dirty Harry to Changeling. Was that the attraction of this script?
I grew up with J. Edgar Hoover. He was the G-man, a hero to everybody, and the Federal Bureau of Investigation was the big, feared organization. He was ahead of his time as far as building up forensic evidence and fingerprinting. But he took down a lot of innocent people, too.

GQ: That’s putting it mildly. By the ’60s and ’70s, Hoover was more famous for being an abuser of power.
Leonardo DiCaprio: I think that’s the essence of this story—absolute power corrupts absolutely. Here’s a man who created the most advanced police force and investigation system the world has ever known. But then as time went on, his obsession with Communism took over. No one else has had such a position of power for that long—to blackmail presidents, to wiretap political leaders, to be able to manipulate the world around him. It was scary.

[To Eastwood] How much did you know about Hoover’s rumored homosexuality?
I’d heard all the various controversies and gossip—that he wore dresses at parties. Everybody was saying, maybe he’s gay because he’d never gotten married. But that’s the way they did it back in the ’40s. If a guy didn’t get married, they always thought, Oh, there’s something wrong with him.

GQ: I talked to Lance Black [the screenwriter], and he is pretty unequivocal about Hoover’s homosexuality. As he told me, “The evidence may be circumstantial, but I think a jury would find him gay beyond a reasonable doubt.” And the scene in which his mother [Judi Dench] almost crushes him by essentially saying she’d rather have a dead son than a gay son seems to suggest that he was gay. Didn’t he have something approaching a long-term marriage with Clyde Tolson [Armie Hammer]?
Clint Eastwood: Well, they were inseparable pals. Now, whether he was gay or not is gonna be for the audience to interpret. It could have been just a great love story between two guys. Or it could have been a great love story that was also a sexual story.

Leonardo Dicaprio: What we’re saying is that he definitely had a relationship with Tolson that lasted for nearly fifty years. Neither of them married. They lived close to one another. They worked together every day. They vacationed together. And there was rumored to be more. There are definite insinuations of—well, I’m not going to get into where it goes, but…

Clint Eastwood: It’s not a movie about two gay guys. It’s a movie about how this guy manipulated everybody around him and managed to stay on through nine presidents. I mean, I don’t give a crap if he was gay or not.

Leonardo Dicaprio: If I were a betting man, I actually don’t know what I would bet [regarding his sexuality].

GQ: Really? You don’t?
Leonardo Dicaprio: I don’t. I don’t know what I would put my money on.

GQ: I have to ask, since it is a movie about Hoover: Did you two talk politics? You’re on pretty different sides of the fence.
Leonardo Dicaprio: Never once.

Clint Eastwood: The politics of the movie was the only politics that we talked.

Leonardo Dicaprio: Hoover allegedly belonged to no party. Just like us when we do movies—we belong to no party!

GQ: Yeah, but maybe between the movies you have some political feelings. [to Eastwood] You’ve described yourself as a social libertarian. What does that mean to you?
Clint Eastwood: I was an Eisenhower Republican when I started out at 21, because he promised to get us out of the Korean War. And over the years, I realized there was a Republican philosophy that I liked. And then they lost it. And libertarians had more of it. Because what I really believe is, Let’s spend a little more time leaving everybody alone. These people who are making a big deal out of gay marriage? I don’t give a fuck about who wants to get married to anybody else! Why not?! We’re making a big deal out of things we shouldn’t be making a deal out of.

Leonardo Dicaprio: That’s the most infuriating thing—watching people focus on these things. Meanwhile, there’s the onset of global warming and—

Clint Eastwood: Exactly!

Leonardo Dicaprio: —and these incredibly scary and menacing things with the future of our economy. Our relationship to the rest of the world. And here we are focusing on this?

Clint Eastwood: They go on and on with all this bullshit about “sanctity”—don’t give me that sanctity crap! Just give everybody the chance to have the life they want.

Leonardo Dicaprio: It’s the great diversion. Politicians are masters at getting you to be on their side so that you don’t look at how big business—

Clint Eastwood: I love big business! [They both laugh.]

Clint Eastwood: I love big business if it hires everybody and does all the right things, and if they get off track then they’ll have to deal with whatever—

Leonardo Dicaprio: But they often do get off track, unfortunately. See, now you’ve got us in a political debate!

GQ: Speaking of business, the movie kind: One thing you’ve both seen grow is a public obsession with box office. By Sunday afternoon, everybody knows how everything did. These days, when you have a flop, does it hurt more to have it—
Clint Eastwood: —broadcast all over the place? You know, it’s really crappy. If it doesn’t do well that first weekend, screw it. But you make a film to make a really good film, and if people don’t embrace it, there’s nothing you can do. You’ve always gotta remember that a lot of great movies didn’t do anything. Everybody would like to have the business that some of these turkeys do, but would you be proud to have your name on them? Not particularly. Would you love to have the bank account? Sure. I made a good living. But that was just lucky. If I’d made a mediocre living, I would have felt the same way.

Leonardo Dicaprio: Throughout my career, I never knew which movies of mine made money and which didn’t. When Titanic came out, people would say, “Do you realize what a success this is?” And I’d say, “Yeah, yeah, it’s a hit.” The [money] stuff never mattered to me until I was into my thirties and got interested in producing, and people would show me charts explaining what finances a movie, what you’ll make from foreign, what you’ll make from domestic, what you need to make an R-rated film that’s a comedy versus a drama. But even now I say that unless you want to prove that you can carry a film with your name, continuously trying to achieve box-office success is a dead end.

Clint Eastwood: If Leo had been running around in tights and a cape doing comic-book movies and came to me and said, “Hey, I want to play Hoover,” I don’t know. I would have thought…

Leonardo Dicaprio: “How’s he gonna fit into these tights?” [Eastwood laughs.] Where are the days when someone like Warren Beatty could [keep campaigning for months for] Bonnie and Clyde and, because of that, critics see it again and it’s rereleased and becomes a classic?

GQ: [To DiCaprio] You never had that period that a lot of young actors had Leonardo Dicaprio: where you’re taking work to get into the business and pay the rent.
My introduction to acting in films was with De Niro in This Boy’s Life. When I got the part I was 15, and somebody said, “Do you realize who you’re gonna work with?” I said, “Yeah, I guess.” And they said, “No, no, no. Go watch all of his films, and then go see these people’s films.” So I obsessively watched films on VHS, and I remember feeling so overwhelmed by what had been done in cinema already. Watching a young Brando or James Dean or Montgomery Clift, I was like, Oh, my God, how can anyone ever hope to achieve that type of greatness?

Clint Eastwood: Well, that’s admirable. You can find execs in studios around town—they don’t care about history, or even know what they have in the vaults. They just get in, make a few deals, and move on.

GQ: [To DiCaprio] What kind of roles would you have played if you had been a leading man at another time?
Leonardo Dicaprio: For my generation, it’s always the ’70s. That period where you felt like the hands were being dealt back in the director’s favor. The studios realized that letting them tell their stories was something the audience had a hunger for. And of course, it all went awry. [They both laugh.] Taxi Driver to me is the ultimate independent-movie performance. Playing a character like Travis Bickle is every young actor’s wet dream.