The film opens with Arizona deputy Walt Coogan (Eastwood) on the trail of an Indian fugitive; on catching him, he handcuffs him outside the house of a married woman with whom he is having an affair; but his sheriff catches him in the bath, and as a punishment for his cruelty to his prisoner he is sent to New York to escort back James Ringerman (Don Stroud), who is wanted in Arizona. However, when he arrives in the city he is told by Sheriff McElroy (Lee J. Cobb) that Ringerman cannot be transported yet, since he is suffering from an overdose of LSD. Annoyed at having to stay longer than he'd intended in New York, Coogan passes the time by flirting with probation officer Julie Roth (Susan Clark).
After spending a night in a very seedy hotel, Coogan gets impatient with the red tape, and so goes to Bellevue hospital and bluffs the staff into releasing Ringerman into his custody. Ringerman's girlfriend Linny Raven (Tisha Sterling) overhears Coogan's travel plans, and so arranges a reception committee for Coogan at the heliport. Coogan is hurt badly and winds up in hospital, with Ringerman on the loose with Coogan's gun. When he discharges himself, he is ordered by McElroy to return to Arizona; Julie invites him to dinner, and it transpires that Linny Raven is one of Julie's probation cases, and when she is in the kitchen Coogan raids her filing cabinet and finds out Linny's address. Coogan finds Linny in the Pigeon-Toed Orange Peel club, and goes back to her apartment with her, where he first seduces her and then gets her to lead him to Ringerman.
She takes him to a pool room, where he gets into a fierce fight with a number of Ringerman's gang. Although outnumbered, Coogan puts up a very strong fight before being beaten up, saved by the arrival of the police. Coogan leaves before they arrive, however, and goes back to Linny Raven's apartment, where he hits and threatens her until she takes him to where Ringerman is hiding. She leads him to the Cloisters, where Ringerman shoots at him before fleeing on his motorbike. Coogan requisitions another bike, and there follows a gripping high-speed chase through the park, which ends with Coogan leaping from his bike onto Ringerman's, knocking him off. When Ringerman has recovered, Coogan takes him again to the heliport, where McElroy returns to him his distinctive hat which he lost in the pool room fight; Julie is also there to see him off.
Coogan's Bluff provided a stepping stone into the present day for Clint Eastwood. The character he plays is not totally removed from the Man With No Name, but he is placed in an alien environment; he is about half-way between his Western persona and the character of Harry Callahan, which he would take up a couple of years later. The fish-out-of-water scenario is an effective one, and Clint portrays very effectively Coogan's bemusement at the differences of the big city. Like Harry Callahan, Coogan has a problem with red tape and authority, and like nearly all of the characters Clint has portrayed, there are definite character flaws, which make him more believable and accessible to the common man.
The film also marked Clint's first work with director Don Siegel, a man who was to prove very influential to Clint's directorial style. Already Clint was very interested in the directorial process: he passed on tips to Siegel that he had learned from watching Sergio Leone at work, and he also got involved by helping to choreograph and film the pool room fight, a superb piece of action cinema.
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