Though Damon and Eastwood hold different political views — the youngster is a progressive from Cambridge, Massachusetts; the old guy is a libertarian whose family drifted all over the West — both are prickly individualists who believe that the proper use of power is the pursuit of independence. “It’s easy to fall into that trap of following what’s being made now, what people like,” says Damon. “But if you fall into that calculus, you’re already completely fucked. You have to do something that you believe in and that you like.” This accounts for his artistic crush on Eastwood, who’s been doing what he likes for decades now and started at about 40, Damon’s age, when he directed and starred in Play Misty for Me.

“If you listen to somebody else,” says Eastwood, shaking his gray head, “they could talk you out of anything. I’ve had people try to talk me out of The Man with No Name right up through Gran Torino.”

To bring home the point that it’s futile to follow fashion — not because fashion is contemptible, but because it’s unpredictable — Eastwood tells a story while Damon sits back and settles into pupil mode. The Harvard dropout who headed to California for a screen career is back in class now, learning from the professor of his dreams.

“I remember when I first went to Italy to do Fistful,” Eastwood recalls, his features bemused and bright. “I came back, and the trades had big articles, westerns are dead, and I said, ‘Shit, I make one and they’re out.’ Then all of a sudden an article came out that says there’s this little picture in Italy that’s really doing great business, and I didn’t even know I was in it because it was made under another title, The Magnificent Stranger. Then, later, I read another piece and saw that it was a Clint Eastwood movie, and all of a sudden the phone started ringing.”

It’s an instructive anecdote about the folly of timing and controlling life and the necessity of trust — trust in one’s self and trust in fate. Eastwood is a cheerful fatalist, not an anxious perfectionist, and there are times when his affect, manner, and attitude are strikingly reminiscent of Ronald Reagan, whom he used to visit in the White House. Freeman sums up his pal’s philosophy with the old chestnut, “Go placidly among the noise and haste,” but another way to put it is: Do your job, help others do theirs, and then relax and let what happens happen.

This may not sound like an orthodox macho creed, but Damon gets it. As a fellow interpreter of hypermasculine characters, he knows that manhood doesn’t always announce itself by bellowing orders and slamming doors. In Martin Scorsese’s The Departed, Damon played an impotent cop whose weaknesses he chose to emphasize rather than camouflage: “I went up to Marty and said, ‘I want to lose every fight I’m in and I don’t want my dick to work.’

“Anybody I’ve met in my life who really is tough,” Damon continues, “there’s no swagger, there’s no raising your voice. You sit down and talk to a guy from the Delta Force, it’s very pleasant and calm.”

Eastwood couldn’t agree more. After claiming he’s never thought much about manhood (he uses the word “dwell” again), he reveals that he’s thought about it plenty. “I remember when I first got in the movie biz, everyone was talking about, ‘Play it like this.’ And I thought, Why do you have to do it? Rocky Marciano was the toughest guy in the world, and he shook hands with me, and he didn’t come in all Texas. It was as gentle as any woman’s handshake. Yeah, he didn’t have to break my hand. He didn’t feel he needed to show off. In his profession he’s exerted a lot of violence, but he wasn’t a violent person.”

A young female Warner Brothers employee appears. It’s time for Eastwood and Damon to leave the table. They have a busy day ahead of them, full of duties in preparation of the Hereafter premiere. Damon pops up like a jock, spring-loaded for whatever’s next, but Eastwood stands up like a senator, deliberately, in a series of stately little stages that attract looks from all over the hotel’s lobby. I ask him before he follows Damon out if he plans to appear onscreen again.

“Act again? I have no rules. There are no rules,” says Eastwood. “At my age, there aren’t that many good roles to play. Sure, I’d do it, but I’m not looking for it.” His voice is mellow and reflective. I flash back to a comment he made earlier about the white-light near-death experiences that are touched upon in Hereafter: “I’ve come pretty close myself a couple of times.” Then he says goodbye and shakes my hand. Gently. Like a woman. Like a man.

—

This article originally appeared in the November 2010 issue of Men’s Journal.

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