20. Every Which Way But Loose (1978)
Against all advice, Clint Eastwood switched direction with a knockabout comedy that would be one of his biggest hits. He plays a bare-knuckle fighter who falls for a country singer, though the real romantic chemistry is between him and Clyde the orangutan. Barroom brawls aplenty! Ruth Gordon (as “Ma”) v Nazi bikers!
19. Million Dollar Baby (2004)
In a role that fits him like a comfy old overcoat, Eastwood plays a curmudgeonly boxing trainer who reluctantly takes on a waitress and soon-to-be surrogate daughter (Hilary Swank). But disaster strikes … Eastwood also directed, and the film won multiple Oscars, despite (or perhaps because of) its controversial ending.
18. Kelly’s Heroes (1970)
Dirty Dozen-lite meets The Italian Job as Eastwood leads his platoon in a heist comedy set in France in 1944. Eastwood is solid, but gets comprehensively upstaged by Donald Sutherland’s stoned tank commander. Jolly good fun, though the slapstick sometimes sits awkwardly with the horrors of war.
17. Space Cowboys (2000)
Eastwood directed this amiable geriatric riposte to Armageddon, and reunited with Sutherland, alongside James Garner and Tommy Lee Jones, to play retired test pilots launched into space to save the world from obsolete satellite tech. Plot, dialogue and brawling are all 100% predictable, which only adds to its charm.
16. Gran Torino (2008)
“Get off my lawn!” Septuagenarian Eastwood directs himself as a racist Korean war veteran who bonds with his Asian neighbours in blue-collar Detroit. The action and dialogue are a little clunky, but viewed in light of his long career, even the clunkiness becomes rather moving.
15. Where Eagles Dare (1968)
Eastwood and Richard Burton co-star in a cracking Alistair MacLean action pic in which they infiltrate a Schloss in the Bavarian Alps. Result: explosions, stunts galore and Nazis falling like ninepins. All this gung ho budgetary extravagance inspired Eastwood to found the parsimonious Malpaso Productions.
14. High Plains Drifter (1973)
Eastwood’s first western as a director was a gothic homage to Sergio Leone and Don Siegel, the film-makers who shaped his early career. As “The Stranger”, he rides into a frontier town to wreak semi-supernatural vengeance on the townsfolk, using methods that include getting them to paint the town red – literally.
13. Escape from Alcatraz (1979)
After a production dispute, this taut fictionalisation of a real-life 1962 escape attempt would be Siegel and Eastwood’s final collaboration. Clint plays Frank Morris, banged up on the notorious prison island in San Francisco Bay, ruled by Patrick McGoohan as an unyielding warden. Filmed on location in Alcatraz itself.
12. Tightrope (1984)
Richard Tuggle gets the credit, but Eastwood allegedly ended up directing most of this underrated thriller himself. In one of his most fearlessly uningratiating performances, he subverts his own macho persona as New Orleans cop Wes Block, whose sexual kinks are uncomfortably similar to those of the serial murderer his department is hunting.
11. In the Line of Fire (1993)
Eastwood never balked at acting his age, and visibly gets short of breath as a veteran Secret Service agent, still depressed by his failure to protect JFK, who is forced into a battle of wits against John Malkovich. Smart directing from Wolfgang Petersen lifts this into almost-classic thriller territory.
10. Two Mules for Sister Sara (1970)
After Coogan’s Bluff, Eastwood’s second film for Siegel was this spaghetti-adjacent western with an Ennio Morricone score, filmed in Mexico. Clint plays an American mercenary who rescues a nun (Shirley MacLaine) from bandits. They join up with Mexican revolutionaries to fight the occupying French forces. Breezy fun with an action-packed finale, and you’d never guess Clint and Shirley weren’t best mates on set.
9. The Bridges of Madison County (1995)
Eastwood’s no-nonsense directing style is perfectly suited to this Brief Encounter-type romance, adapted from a bestselling novel. He plays a peripatetic photographer who stops taking pictures of Iowa’s historic bridges long enough to have a passionate affair with a local housewife (Meryl Streep in frumpy frocks). Acting-wise, Eastwood wisely leaves most of the emoting to his co-star, with results that are genuinely affecting.
Michael Cimino made his directing debut with this likable buddy caper movie set in rural Montana. Eastwood gives one of his most underrated performances as a fugitive bank robber who teams up with Jeff Bridges’ cocky young drifter. Knockabout comedy rubs shoulders with brutal violence, new Hollywood-style, as a getaway goes horribly wrong and the typically 1970s ending is a heartbreaker.
7. The Beguiled (1971)
With three releases cementing and subverting his tough guy persona, 1971 was a watershed year for Eastwood. In Siegel’s unnerving southern gothic thriller (remade in 2017 by Sofia Coppola), he plays a wounded Yankee soldier trapped in an all girls’ school in rural Mississippi, where his attempts to manipulate the women’s emotions only result in him being systematically unmanned.
6. Play Misty for Me (1971)
Sixteen years before Fatal Attraction, Eastwood made his directing debut with a psychological thriller in which his strapping DJ is reduced to a nervous wreck by a slip of a woman (Jessica Walter AKA Arrested Development’s Lucille Bluth) as their initially casual relationship leads to jealousy, stalking and scissor attacks. Filmed in Carmel-by-the-Sea, California, where, from 1986 to 1988, Clint would serve as mayor.
5. A Fistful of Dollars (1964)
Hitherto best known as Rowdy Yates from TV’s Rawhide, Eastwood took a risk in playing a poncho-clad anti-hero, The Man With No Name, in a low-budget Italian production with a Morricone score. The gamble paid off. Leone’s unauthorised remake of Akira Kurosawa’s Yojimbo (itself a reworking of Dashiell Hammett’s Red Harvest) gave birth to the spaghetti western subgenre. And a screen icon was born.
4. The Outlaw Josey Wales (1976)
Eastwood controversially ousted Philip Kaufman to take over directing on one of his most enjoyable westerns. A farmer hunts down the soldiers who murdered his family, but vengeance is deferred while he acquires a surrogate family of misfits, including Chief Dan George as the Cherokee who can’t sneak up, and Sondra Locke in the first of six films she made with Clint, her real-life partner.
3. Dirty Harry (1971)
Eastwood added another signature role to his repertoire in the first of five films featuring poster boy for police brutality Inspector Harry Callahan, as he goes after the psychopath terrorising San Francisco. Director Siegel keeps it gritty and exciting, and Clint, road testing a 1970s pompadour, makes Harry cool, instead of just a vigilante thug.
2. The Good, the Bad and the Ugly (1966)
The final part of Leone’s Dollars Trilogy adds Eli Wallach as comic foil to the dream team of Eastwood and Lee Van Cleef, who last met in For a Few Dollars More (1965). All three play scumbags on the trail of buried treasure, set against an epic American civil war backdrop. The squinty showdown in the cemetery, choreographed to Morricone’s score, is peak cinema.
1. Unforgiven (1992)
Eastwood stars in this Oscar-winning western as William Munny, a widowed pig-farmer who thinks his bounty hunting days are over (“I ain’t like that any more”) until he hears about a $1,000 reward on the heads of men who slashed a sex worker’s face. But first he has to get past Sheriff Gene Hackman. With the director-star completely in control of his screen persona and drawing on his history of playing violent men, he builds without irony towards a showdown that is more tragic than cathartic.