Any discussion of Tony Bennett within the context of a book on jazz ought to start with the disclaimer that he is not, never was, and doesn't claim to be, a "jazz singer" per se. However, there isn't any question that Bennett has always felt a kinship with jazz musicians and has collaborated with them several times in his long career, often with delightful results. Though not an improviser, Bennett could always follow the contours of a jazz rhythm section with confidently jazzy inflections; indeed, he sounds absolutely ebullient whenever he records with jazzers. Bennett's pianist and musical director since the 1950s, Ralph Sharon, is a solid, dependable jazzman in his own right, and has occasionally steered his boss away from the all-American easy-listening ballad into a more jazz-oriented setting. Bennett counts among his influences Art Tatum, from whom he drew ideas on phrasing and breathing, Mildred Bailey for her relaxed delivery, and of course, the inevitable Billie Holiday and Frank Sinatra, who once proclaimed Bennett to be the best singer in the business. Indeed, as Sinatra's voice aged, Bennett found himself in the position of being the leading purveyor of American popular songs by 1990.

The jazz influence on Bennett was inevitable for a child of the big band era, and his teacher Miriam Spier urged him to listen to instrumentalists instead of singers for inspiration. He worked as a singing waiter as a teenager, sang with military bands during the war, and appeared on Arthur Godfrey's Talent Scouts. Bob Hope heard him performing at a New York nightclub with Pearl Bailey in 1950 and booked him into his show at the Paramount Theatre, where his rendition of "Boulevard of Broken Dreams" attracted the attention of Columbia Records head honcho Mitch Miller. After some early setbacks, Bennett started to put together a string of hit singles like "Because of You," "Rags to Riches" and a pioneering pop cover of a Hank Williams tune, "Cold, Cold Heart" -- all of which went to number one. With his commercial flanks covered, Bennett was occasionally allowed to use the LP format to experiment with jazz in the 1950s, recording with the likes of the Count Basie Orchestra, Ralph Burns, Bobby Hackett, Stan Getz and Zoot Sims. Perhaps his most successful and unusual experiment was a lively 1957 album called The Beat of My Heart, dominated by the drums of Chico Hamilton, Art Blakey and Jo Jones and populated by the likes of Nat Adderley, Herbie Mann, Al Cohn, Kai Winding and Milt Hinton.

Bennett got through the first decade and a half of the rock & roll invasion mostly unscathed, thanks in part to an occasional smash hit like "I Left My Heart In San Francisco" that would thrust his name back into the public consciousness. But the pressures of resisting the rock trend drove Bennett away from Columbia in 1972, and after a brief period with MGM, he made several albums for his own Improv label, DRG and Fantasy, collaborating with Ruby Braff and Marian and Jimmy McPartland and making two now-revered duet albums with Bill Evans. From 1979 to 1986, however, he was unable to secure a recording contract on his terms, and interviews from the period found him quite bitter about the dominance of rock in the music business.