Unforgiven, his Western magnum opus.
His titular character begins as a simple Missouri farmer at the end of the Civil War, and he gets maybe 60 seconds of peace before his homestead is attacked, and his wife and child are killed, by a band of bloodthirsty Jayhawkers. Seeking revenge, he joins a band of bushwackers led by Captain Fletcher (icy John Vernon, aka Dean Wormer), but as the war ends, Fletcher convinces them to surrender to the Union Army. Josey refuses, and good for him; the men are massacred, though Josey intervenes and fights back, managing to escape with young, injured Jamie (Sam Bottoms). The pair set off for Indian Nation, "a good place to hole up," Josey says, "and get you healed up." But the Union men are in pursuit--accompanied by Fletcher--and track him as he inadvertently accumulates several fellow travelers.
The screenplay by Philip Kaufman and Sonia Chernus (from Forrest Carter's book) has an episodic, almost elliptical structure, sometimes playing less as a disciplined narrative than an accumulation of events--and peculiar characters. The picture is filled with scores of wonderful little characters, some only seen briefly: the opportunistic ferry operator, the slimy medicine man, the feisty and hard-nosed matriarch he picks up along the way, the pipe-smoking "Granny" who recognizes the outlaw, and intends to do absolutely nothing about it. Best of all is Lone Watie (played by Chief Dan George from Little Big Man), who makes his first entrance emerging from an outhouse, an oddball character with a wry sense of humor ("I didn't surrender. But they took my horse and made him surrender"). His wily energy compliments solemn Eastwood well, particularly when Josey discovers him, mid-coitus, with the young Navajo woman (Geraldine Keams) they're traveling with. Lone Watie's retort: "I guess you were right--I ain't that old after all." Vernon makes for a complicated, nuanced pseudo-antagonist, although he disappears for long stretches.
The joke was always that Eastwood was less actor than slab of granite, but there's emotion in this performance--whether subtle (his send-off of the kid Jamie, a relationship that mirrors his with the Scholfield Kid in Unforgiven) or pronounced (weeping at the graves of his wife and child). But he mostly does what he does best--chews up and spits out well-written (and frequently funny) macho dialogue. When Jamie asks where they should bury a pair of bounty hunters they've dispatched, Josey growls, "To hell with them fellahs. Buzzards gotta eat, same as the worms." When he's recognized by several Union soldiers, the stare-down is punctured by his challenge, "You gonna pull those pistols or whistle Dixie?" And when a mangy hound tries to join their peculiar caravan, he sputters, "Might as well ride along with us... hell, everybody else is." In that moment, and in several others, he uses his tobacco spit as an ingenious and effective comic prop.
As a filmmaker, Eastwood is experimenting a bit; the attack of the comancheros is weirdly visceral, almost surreal (it's such a good sequence, you wish that there wasn't so much troublesome lingering during the aborted gang-rape that follows), and the flash-cutting as Josey remembers the attack on his home is blunt and forceful. The film was to be directed by screenwriter (and, later, Right Stuff director) Kaufman, and the film even began with him at the helm until a dispute (the details remain murky) between Kaufman and Eastwood ousted the young filmmaker. Who knows how different Kaufman's film might have been, but Eastwood was clearly up to the task.
There are a couple of minor problems--this Jayhawker (and now Yankee) is always a little uncomfortable with these pro-Confederacy stories, and the romance with Sondra Locke (Eastwood's future partner, in the first of her six appearances with him) while sweet, is a bit of a dude--it's mostly just a time killer around the two-hour mark, when the film needs to be tightening, not slacking. But those are inconsequential concerns, and don't do much to derail the picture.
Near the end of The Outlaw Josey Wales, the title character engages in a negotiation with chief Ten Bears (Will Sampson) that is, within the Western canon, almost revolutionary. But by that point in the picture it seems entirely plausible, so subtly and masterfully has Eastwood crafted this familiar yet nuanced work. By the time it reaches its low-key, elegiac ending, the filmmaker seems incapable of stepping wrong. This is an exquisite, intelligent, and surprisingly timeless Western.
"The Outlaw Josey Wales" is available now on Blu-ray. For full A/V and bonus feature details, read this review on DVD Talk.