I have a Clint Eastwood problem. But a new mega-set of his movies, Clint Eastwood: 35 Films 35 Years at Warner Bros., obliges me to take the long view. This is said to be the biggest box set ever devoted to a single filmmaker, dwarfing the hefty Ford at Fox or Criterion’s AK 100: 25 Films of Akira Kurosawa.

The collection’s title is symmetrical but inaccurate if you take it literally. Eastwood has hung his shingle on the Warner lot since filming The Outlaw Josey Wales in the mid-’70s, venturing out only for rare occasions like 1993’s In the Line of Fire. But the set begins with the 42-year-old Where Eagles Dare, a big-budget action-adventure made before the low-key Eastwood “brand” was fully established. (It’s the one where Clint kills dozens of Nazis and lets Richard Burton do the talking.) Next up is the equally explosion-happy Kelly’s Heroes, where the actor aims his famed squint in the direction of cut-up co-stars Don Rickles and Donald Sutherland. Those two films were produced by MGM, whose library is now in Warner Bros.’ possession. As Eastwood fulfilled a contract with Universal (which financed his first films as director, starting with 1971’s Play Misty for Me) he clinched his stardom in the Warner-produced Dirty Harry pictures, then stayed put, turning out the good (Josey Wales is I think the best of his self-directed Westerns), the bad (1997’s Absolute Power and Midnight in the Garden of Evil didn’t make anyone’s day) and the ugly (Warner has done the celebrant no favors by including the likes of 1989’s Pink Cadillac and 1999’s True Crime).

What is true is that Eastwood has been friends with Richard Schickel since Time’s veteran film critic first interviewed him in 1976. Schickel, an Emmy-nominated writer, producer, and director of film-related documentaries, had Eastwood narrate his 1991 TNT program Gary Cooper: American Life, American Legend, made a pair of shows about Eastwood in conjunction with his Oscar-winning breakthrough Unforgiven (1992), and in 1996 published an admiring but not uncritical biography of him. New to this set of reissues is a 24-page booklet adapted from Schickel’s monograph Clint: A Retrospective, which will be published on March 1, and a 22-minute excerpt from his upcoming documentary The Eastwood Factor, which will premiere in full on Turner Classic Movies in late May to coincide with Eastwood’s 80th birthday then be available on DVD.

Schickel has been every which way but loose with Eastwood, and talking with him jogged my thinking. “I met him right after Josey Wales came out, at the home of a mutual friend here in Los Angeles,” he recalled when I spoke with him last week. “It sort of happened the way any friendship happens; if I was out here I’d give him a call, and if he was in New York he’d do the same. In the ’80s, when I moved here permanently, is when we started working together, and our relationship evolved into something that’s mutually supportive.” He says Eastwood is his only filmmaker friend. “Right now I’m finishing a book called Conversations with Martin Scorsese. I’d known him casually before that, and we’ve come to be a little closer, but it’s different.”

Over time Schickel has formed a different opinion of Eastwood. “I didn’t at first like the spaghetti Westerns. I’ve come to like them a lot—they’re among his best movies—but I was more of a traditionalist. They were a radical departure and it took time for me to wrap my mind around them.”

Then, the revelation. “The first movie of his that really made me stop and think was Don Siegel’s The Beguiled (1971), a really interesting commentary on masculinity. It questions the values that Clint had represented, and made me think that this guy was of more interest than I thought. I came more to grips with him as he made different kinds of movies, which he did rather intelligently, taking small steps to where he’s at now. Honkytonk Man (1982), Bird (1988), and White Hunter, Black Heart (1990) are among those pictures that led up to the quantum leap of Unforgiven, then on to Mystic River (2003), Million Dollar Baby (2004), and Letters from Iwo Jima (2006).”

Here we part ways. Unforgiven was indeed a quantum leap, and a much better film when I saw it a second time (and on subsequent viewings). But I’ve been colder to most of his pictures since. I’m just not sure his talent, or his patience, is up to all of them. (What a few more takes, and more time in the editing room, could have done to improve, say, Mystic River.) Surprisingly, one I liked was 2008’s Changeling, made outside Warner; despite overlength and a certain sketchiness, the weaknesses of his approach, it grabs onto its stranger-than-fiction true story and never lets go, through to a beautifully realized final shot. (But I confess to skipping Invictus, which even Eastwood partisans walked away from. I hear it’s not bad, but “not bad” doesn’t stir me to action, except to drop it into my Netflix queue.)

I can’t disagree with Schickel on one point. “What’s most remarkable is that he’s at an age where most filmmakers are running around getting tributes at film festivals. He’s a very active, questing guy who’s taken on a range of subjects. The picture he just finished shooting in England a couple of weeks ago, Hereafter, is a really interesting piece about near-death experiences. (Starring Invictus’ Matt Damon, the film, due in December, is written by Peter Morgan, a two-time Oscar nominee for The Queen and Frost/Nixon.) He said to me once, ‘I could have kept doing Westerns and cop pictures, which were very successful for me. But they were never enough.’”

Schickel recommends 1993’s A Perfect World as an underrated film worthy of rediscovery in this new set. I’d say 1984’s Tightrope, a noir-ish “commentary on masculinity” movie that was a hit in its day, is worth a second look in the context of his renaissance.

Not that the filmmaker goes in for strolls down memory lane. But these make for some nice vignettes in Schickel’s documentary, as he tickles the ivories (and plays the Mystic River theme) at the Eastwood Scoring Stage and visits the New York set where his beloved Bird was shot and a house set where the poignant finale of Million Dollar Baby was staged. There’s an amusing scene where he revisits his old costumes. They look as if they’d all still fit—except maybe for that hippie-era thing he pulls out from Play Misty for Me. “I’m not sure he’d ever been in the costume storage facility on the lot when we took him around. I think even he was surprised by how much they had,” Schickel says. “Except for some hair loss he’s pretty much intact, and very fit; his body weight has probably changed about two pounds since I’ve known him.”

Did the recognition he received from Unforgiven change him? “He’s as competitive as the next guy,” Schickel says. “If he’s nominated for an Oscar he wants to win it. But if he doesn’t he just move on to the next thing.”

Newsflash: The next thing may very well be a return to acting. Rumor has it that Eastwood wouldn’t get off his lawn and step in front of the camera after the huge success of 2008’s Gran Torino, but Schickel’s not so sure. “I don’t think he’d direct himself again, which is too exhausting. But I can see him acting in someone else’s movie, maybe take on a supporting role.”

What neither friend can envision is retiring. Says Schickel, “I’m almost his age but for me, like for Clint, the work is everything.”

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