The boldest role ever undertaken by a major star of Frank Sinatra’s generation – and little thanks he got for it. Not only was he virtually unrecognisable under a slab of make-up that George Hamilton would have envied but the role was a complete reversal of his screen persona. Admittedly, he had flipped that persona for Tony Rome (1967) and as the cuckolded cop in The Detective (1968), but this was on a completely different level.
Sinatra was no Tom Hanks or Daniel Day-Lewis, known for inhabiting different types of characters, and, while he did have a vulnerability that he put to good use in The Manchurian Candidate (1962) and The Man with the Golden Arm (1955), he was best known on screen as the guy in charge.

That was far from the case here. Dumb and dumber might be more apposite. Dingus Magee (Frank Sinatra) is a scamp, an outlaw so useless he is worth only $10 in reward money, who steals the stash of old rival Hoke Birdsill (George Kennedy), triggering a revenge caper that is complicated by a host of unnecessary complications by director Burt Kennedy (Welcome to Hard Times, 1967) who has set his heart on some kind of satirical comedy western with a revisionist slant.
So we get a female mayor, Belle (Anne Jackson), who happens to own the local brothel, whose commercial prospects are endangered when the local Cavalry are called away to fight the Native Americans, an Indian chief Crazy Blanket desperate to trade his daughter for a rifle, and when that looks like not working out calling on any available squaw to seal the deal, predatory schoolteacher Prudence (Lois Nettleton) and a running gag involving a Brown Derby hat that results in a gunfighter (Jack Elam) being mistaken for Magee.
It’s a bit long on complications and short on satire and is rescued by the double act of Magee and Birdsill, who constantly get in each other’s way or try to pull a fast one. Birdsill, as it happens, is appointed sheriff, since that’s in the purview of the mayor, and, on the right side of the law for the first time in his life, makes an ill-fated attempt to do good.

Magee tries to help him along. In exchange for the sheriff turning a blind eye for a period of time to Magee’s nefarious activities, the reward for the outlaw will mushroom, permitting greater kudos for the sheriff on his capture.
The main problem is that Kennedy directs with a very heavy hand, very obvious musical cues for a start, and there’s not enough that’s intrinsically funny. Though there is a reversal of an obvious joke of Birdsall being sent to the brothel to locate the mayor, expecting to find a client not the owner.
But both Sinatra and George Kennedy (The Sons of Katie Elder, 1965) are a delight, the latter also playing against type rather than his usual dominating character. Their dumbness takes some beating. Sinatra just about gets the upper hand, but there’s not much in it.
The best thing about the picture is the sense of reality. The U.S. Cavalry spend more time in the brothel than out hunting Native Americans. Law and order can go to hell as long as everyone is having illicit fun. The respectable schoolmarm proves a skilled seductress. Peace is desirable because it is more profitable than war. And the bulk of the outlaws in the Wild West are far from achieving legendary status, just two-bit punks.
Not surprisingly, this was a massive flop and killed off Sinatra’s movie career for the rest of the decade – not that he was overly concerned, “My Way” having reignited his singing career and he was a Vegas regular. But it’s a shame the acting was so vilified, Roger Ebert blamed Sinatra rather than the director for its failure, in particular taking him to task for the one-take approach that Gena Rowlands previously exalted (but what does she know, she’s just an acclaimed actress and knows how a movie works better than a critic).
Well overdue for a reappraisal and if you go in duly warned you might even enjoy it, or at least the Sinatra-Kennedy double act.
That’s a wig on Sinatra, right? Can’t think of another film where they put a wig on him…looks like one of Bronson’s cast offs…
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Looked okay on Bronson. Sinatra was known, like Wayne, for wearing a toupee but this looks like they put three toupees on by mistake.
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