On the trail of buried treasure … Clint Eastwood in The Good, the Bad and the Ugly. Photograph: TCD/Prod.DB/Alamy
20. Every Which Way But Loose 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 v Nazi bikers!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 . But disaster strikes ...
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.“Get off my lawn!” Septuagenarian Eastwood directs himself as a racist Korean war veteran who bonds with his Asian neighbours in blue-collar Detroit.
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.Richard Tuggle gets the credit, but Eastwood allegedly ended up directing most of this underrated thriller himself.
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 gave birth to the spaghetti western subgenre. And a screen icon was born.Eastwood controversially ousted Philip Kaufman to take over directing on one of his most enjoyable westerns.