Though Frank Sinatra's reputation as celebrity, icon, bad boy, and possibly the greatest singer of American popular songs of the century are paramount to the general public, he has always been valued highly in the jazz community, especially among musicians. Though not a jazz singer per se, he was a child of the big-band era, incubated with an ability to swing in a relaxed, ingratiating way in all kinds of material. Whenever he had the chance, Sinatra would credit Billie Holiday as a primary influence on his vocal style -- even recording a tribute song called "Lady Day" in 1970 -- and he learned circular breathing at the feet of trombonist Tommy Dorsey. Particularly from the mid-1950s into the mid-1960s, Sinatra would use expert jazzmen prominently in his recording orchestras, as well as arrangers who cut their teeth in the big-band era. He was at his freest and loosest when paired with a great big band like that of Count Basie, where he would bend to the rhythm, embroider the melody, and stray from the tune to the point where non-jazz-oriented aficionados of singing would become disoriented. Indeed, the theory has been advanced that during the `60s, flinging himself head-on against the rock & roll tide of the time, Sinatra was actually able to revive the big-band era in terms of mass popularity, record sales, concert receipts, and media exposure -- although this time, the orientation was in favor of the singer rather than the band. Had he chosen to explore it more, Sinatra could have also been the most important bossa nova singer of his time; even so, the two albums he did make with Antonio Carlos Jobim display an uncanny emotional affinity for the idiom. Other than Brazilian music, though, Sinatra stayed away from developments in jazz beyond swing (unless one counts a quirk like his notorious "do-be-do-be-do" scatting at the close of "Strangers In the Night").

The son of an ex-boxer and a domineering, ambitious mother, Sinatra quit school early in order to begin his musical career, winning the Major Bowes Amateur Hour radio contest at 19 as a member of the Hoboken Four. Shortly after leaving Benny Goodman to form his own big band, Harry James hired Sinatra as a featured singer in 1939, and graciously relinquished him to Tommy Dorsey the following year. Backed by the vocal group the Pied Pipers, Sinatra's star rose to the point where in 1942, he broke out of the Dorsey ranks with four solo sides on his own. The wild, orgiastic reaction that Sinatra aroused during the war years announced the rise of the solo singer act in pop music, a development that would help send the big bands reeling. Though Sinatra was known mostly for his smooth, straightforward ballads during what are now known as the Columbia years (1943-52), occasionally his primary arranger Axel Stordahl and others like George Siravo would cook up a big-band chart for him. He also recorded "Sweet Lorraine" with the Metronome All-Stars (including Nat Cole and members of the Dorsey and Ellington bands) in 1946 and other intimately jazzy sides with the small combos of Page Cavanaugh, Phil Moore and Tony Mottola.

Upon moving to the Capitol label in 1953, many of Sinatra's recordings took on a tougher, more swinging, jazz-driven edge, with first Nelson Riddle and then, more vehemently, Billy May contributing sophisticated extensions of big-band-era techniques. The apex of the Riddle recordings is Songs for Swingin' Lovers (1955-56), where Sinatra rides confidently along with the swing of the band; May's charts for Come Fly With Me (1957) and Come Swing With Me (1958) push the swing envelope even farther and harder. The move to Sinatra's own label Reprise in 1961 found the singer working with other jazz-grounded arrangers like Johnny Mandel, Neal Hefti and Quincy Jones, as well as May and Riddle. In addition to Sinatra and Swingin' Brass, Hefti wrote the charts for Sinatra's initial studio encounter with Basie, Sinatra/Basie, while Jones did the follow-up, It Might As Well Be Swing, and conducted the live album with Basie, Sinatra at the Sands. A bit late for the bossa nova boom, Sinatra started working with Jobim in 1967 and again in 1969 -- the latter session did not come out in its entirety until 1995 -- and 1967 also saw a one-time-only summit meeting with Duke Ellington's orchestra.