In 1963, the strain of wearing so many hats in the entertainment industry led Frank Sinatra to jettison one of them: he sold his controlling interest in Reprise Records, the head of a record label no longer. Part of that strain had been caused by his difficulties in generating the kind of smash hits on the singles charts that he had enjoyed during his glory years at Capitol, and of his new albums competing with Capitol dumping his back catalogue onto the market at cut-rate price.

The other impact to not just his commercial prowess, but that of everyone else in the music industry, was of course the arrival of the Beatles to the U.S. in the winter of 1964. Far more than Elvis, they changed the nature of the market, and suddenly Sinatra had to compete not simply with a generation gap as he had in the fifties, but a major realignment of purchasing habits that went across a much larger segment of all age ranges.

Enter producer Jimmy Bowen and arrangers Ernie Freeman and Billy Strange, the latter two responsible for ten of the twelve arrangements on Greatest Hits. They helped Sinatra accept and incorporate newer sounds into his instrumental palette, and it showed in the chart placings, with the modern sounds of "Strangers in the Night," "Somethin' Stupid," "That's Life," and "Summer Wind" all making the top 40, the former two both #1, during Sinatra's most impressive assaults on the charts while at Reprise, in 1966 and 1967.

Certainly, the best item here is "Summer Wind," one of the last great collaborations with his mainstay, Nelson Riddle, and the final time one of their works made the radio. But the album is worth buying for the over-the-top, over-dramatic stabs Sinatra did make at commerciality here. The Gordon Jenkins' arranged "It Was A Very Good Year" has a very different meaning here than in the context of September of My Years, and all the songs here have their own very enjoyable charms, for schmaltz factor if nothing else.