Coogan's Bluff (1968)

Deputy Sheriff Walt Coogan (Clint Eastwood) is a thorn in his boss’s side. He is a know-it-all, arrogant and he twists all the rules to his liking. Wanting Coogan out of his way for awhile Sheriff McCrea (Tom Tully) sends Coogan to New York. His mission: to retrieve a prisoner and bring him back to Arizona. Coogan takes off for New York, where he is scorned as a hick from the country. Impatient with the wait because the prisoner isn’t ready, he finagles his way into getting the prisoner (Don Stroud) without having to jump through all the hoops. This little antic fails Coogan when his prisoner escapes. Shamed beyond belief and ordered home, Coogan vows to find the man before he steps foot back in Arizona. He is now out of his element in the Big Apple and time is running out.