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,...