By the mid 60's the American Western was a dying genre and the Spaghetti Western emerged to take its place.

Classic cowboy stars like John Wayne and Henry Fonda were getting older, gaining weight, and couldn't ride like they used to. More than that, American audiences no longer bought the all American boy-scout hero, with his noble intent and incorruptible virtue. Italian director Sergio Leone had a vision for the new western hero: cynical, glib, alluring not for his virtue, but for his style.

Clint Eastwood was not Leone's initial choice for his first western Fistful of Dollars, an adaptation of Kurosawa’s samurai film Yojimbo. After Leone watched an episode of Rawhide that Eastwood appeared in, entitled “The Incident of the Black Sheep”, he ordered Eastwood’s headshot. Leone drew stubble on the actor’s boyish face, broadened his shoulder, inserted a hat low over his brow, and sketched one of Italy’s signature Toscano cigars sticking out of his mouth. He hired Eastwood to play The Man with No Name before ever meeting or talking to him.

The Man with No Name (aka Monco, aka Blondie, depending on the film) is an ambiguous character, defined as an icon more than a person. The only thing we know about him is that he carries a gun with a rattlesnake on the grip, he always wears a hat and poncho and he’s always smoking cigars. Today, chain smoking epitomizes a nervous, unhinged nature, but in Leone’s film Eastwood demonstrates his control and discipline by the way he handles his cheroot. Almost as important as the actual smoking of cigars, is the lighting of them, which is used as a way of assessing moral alignment. The bad guys strike their matches on the boots of hanged men and their teeth, good guys use their own boots or the side of their jeans, The Man with No Name, who rides somewhere in between, lights up on anything from his beard to a hunchback’s hump. Eastwood is constantly relighting his cigars throughout Leone’s films, purportedly because Toscanos were so tightly packed that it was impossible to keep them lit for longer than a few minutes. You always knew a gunfight was about to breakout when Eastwood expertly shifted the cheroot from the front of his mouth to the corner of his lips using only his teeth.

Leone wanted his hero to stand as the symbol of Italian masculinity and all Italian men smoked. Leone himself smoked Double Corona Havanas, cigars that were almost as tall as the stout director. Eastwood hated smoking the Toscanos and after the success of Fistful of Dollars and For a Few Dollars More in pre-production, he told Leone he wouldn’t smoke any more. Leone replied, “You’ve got to. The cigar’s playing the lead part.” The cigar stuck through to The Good, The Bad, and The Ugly.