In his eighties, Clint Eastwood directed the biggest money-maker he has ever been associated with, American Sniper. Modeling himself on his mentor Don Siegel, Eastwood gradually evolved from a meat-and-potatoes genre director to a consummate craftsman and the maker of some true artistic triumphs. Let’s look back at the ten best he’s ever helmed.
10 White Hunter, Black Heart (1990). One of Eastwood’s stranger offerings was this project about the making of The African Queen and its director, John Huston, who in the film is fictionalized, called “John Wilson” and played by Eastwood. Eastwood’s attempts to recreate Huston’s peculiar lockjaw are mixed, but White Hunter is a worthy inquiry into the nature of obsessive artistry and the relationship between an artist’s personality and the caliber of his work.
9. The Outlaw Josey Wales (1976). Eastwood began to explore his sensitive side with his portrayal of an honest farmer and family man who turns into a ruthless desperado after the murder of his wife and child. Classic Eastwood motifs such as barroom showdowns and wickedly barbed one liners (such as “Buzzards gotta eat too,” said over the body of a dead man who doesn’t deserve a burial) are laid over an unusual political foundation, about the pointless savagery at the end of the Civil War, when marauding bands of pro-Union “Red Legs” lay waste to civilian homes. Josey Wales explains in his climactic parley with a Comanche chief that despite dealing death for most of the movie he believes in tolerance, his “word of life.”
8. Sudden Impact (1983). Eastwood rejuvenated the Dirty Harry franchise with this fourth entry, in which Callahan tangles with a gang of rapists yet has an uneasy relationship with one of their victims (Sondra Locke), who shares Harry’s approach to violent criminals. Although some of the film’s themes were approaching cliche at this point, it’s still a highly entertaining action picture that deserves to be remembered for more than its signature one liner (cited by President Reagan in the course of promising to veto tax hikes), “Go ahead, make my day.”
7. The Gauntlet (1977). A Phoenix cop (Eastwood) sent to Las Vegas to bring back a “nothing witness” — a prostitute (Sondra Locke) — is slowly revealed to be a witty reversal of Dirty Harry. This cop thinks he was hired because he was the only man who could do a tricky job. In fact he got the nod because he’s perceived to be dumb and incompetent, a lazy drunk who is not expected to survive a battle with the Mob and corrupt cops in both states who want the hooker dead before she can testify against them.
6. High Plains Drifter (1973) A very Eastwood-y twist on High Noon: An entire town is culpable when a lawman gets whipped to death while the residents look on, and the entire town will suffer the consequences. Eastwood plays a mysterious stranger, a ghost or an avenging angel of the dead man, who rides into an Old West village and is hired to take down the three outlaws who murdered the marshal and are about to get out of jail. The apocalyptic touch — the Stranger orders the town literally painted red, with a sign reading “Welcome to Hell” posted to greet the returning desperadoes — gives the film a stern, pitiless sense of evil that must be punished.
5. Gran Torino (2008). The late-life blockbuster that no one was expecting, this unexpectedly comic and warm story about a Korean War veteran who befriends a group of Hmong immigrants from Laos in a desolate contemporary Detroit struck a chord with contemporary America while also harkening back to, and gently mocking, Eastwood’s 1970s image as a brute preserving order in a rapidly changing society.
4. Unforgiven (1992). A revenge thriller with a strong moral purpose that belongs firmly in the pack of films labeled “revisionist Westerns,” this late-career triumph is perfectly enjoyable on the level of pure entertainment, with memorable comic moments supplied by supporting actors Gene Hackman and Richard Harris. Eastwood’s presence as a sinner paying back a few debts gives the film its fire, though.
3. Heartbreak Ridge (1986) One of the most underrated of all ’80s films, this Marine Corps tale was by turns comic, romantic and exciting, with one of the most drolly accurate portrayals of ordinary garrison life ever seen on film and a sneaky turn from character study to military adventure. A group of slouches with no expectation of combat duty joins the Grenada invasion, illustrating how even seemingly low-intensity missions require intense mental and physical discipline. Eastwood plays the gunnery sergeant who whips them into shape in traditional fashion even as he tries to mend fences with his ex (Marsha Mason) by getting in touch with the softer side he probably doesn’t have.
2. Million Dollar Baby (2004). Perhaps the most emotionally devastating film Eastwood had ever made to that point, this boxing story starred Eastwood as an idealized screen dad who dotes on his sensational boxing protegee, played by Hilary Swank. Before narration by Morgan Freeman became a cliche, Eastwood used Freeman’s voice and presence to frame the movie, to devastating effect.
1. American Sniper (2014). An instant classic, the biography of Navy SEAL Chris Kyle smashed box office records on its way to becoming the highest grossing film of the year, the first serious film for adults to hold that honor since 1998’s Saving Private Ryan. The film was not only a spellbinding character study and a riveting war drama, but it felt like a long-delayed national mourning ceremony for the heroes of the Iraq War, the one that was lost, then won, then finally lost again through sheer political neglect. Through all of the many controversies the war unleashed, Americans were unspeakably grateful to troops like Chris Kyle, a fact that no filmmaker before Eastwood fully understood.