I guess you could call Coogan's Bluff a revamped cowboy movie. The setting may have been updated from Dodge's dusty streets to the asphalt jungle of New York City, but in terms of theme and style, the song remains the same. The film hearkens to a time when justice was simple, when bad guys were bad guys and needed to be caught, without miles upon miles of bureaucratic red tape involved. Of course, it's as true today as it was in 1968 that things don't run so simply, but it's in showing what happens when these two worlds collide that Coogan's Bluff transcends being a standard cop thriller.
The ever-grizzled Clint Eastwood plays Wyatt Coogan, an Arizona deputy sheriff who likes doing things his own way. In his eyes, the crooks he wrangles deserve no mercy at all, having given up their rights the moment they committed their crimes. But this brash attitude has frequently put Coogan at odds with his superiors, so it's no surprise that they jump at the chance to get the guy out of their hair for a while. Coogan is sent to the Big Apple to pick up a prisoner named James Ringerman (Don Stroud) and escort him back to Arizona. The seasoned cop finds this easier said than done — Ringerman's release gets delayed due to a nasty LSD trip. He eventually talks his way into getting the perp into his custody, but when Ringerman makes a run for it, Coogan finds himself a stranger in a strange land, having to play by the city's rules as he hunts down his elusive prey.
Coogan's Bluff was made just a couple years after Eastwood made his cinematic splash in Sergio Leone's legendary westerns. Audiences knew him best as the Man with No Name, so it's understandable that he retain a few aspects of that character for his first modernized leading role. But in doing so, Eastwood, under the guiding hands of director Don Siegel, brought about a contrast between the Old West's ways and how the law is enforced today. Needless to say, Coogan is a man of basic means, viewing New York's tangled legal system more as a hindrance than an aide.