Fearless (Tony Bennett)

Abstract Frank Sinatra, who later called him the best singer in the business, pegged Tony Bennett at the start of his career when he observed, with apparent astonishment, that Bennett had “four sets of balls.” He was probably thinking of Bennett’s dynamic, nervy, over-the-top attack and vocal range, but he proved more discerning than he knew. Two decades later, the remark might have also referred to Bennett’s challenging repertory, heart-on-sleeve emotionalism, actorly inflection of lyrics, or stubborn idealism, which motivated him to leave Columbia Records and go independent when he felt corporate powers cared more about the marketplace than his musicianship. Indeed, it’s impossible to survey Bennett’s 51 years of recordings—capped this month with the almost absurdly demanding Playin’ with My Friends: Bennett Sings the Blues— and not marvel at the guy’s sheer moxie. His daring was apparent from the beginning, when Bennett made the big leap from Astoria, Queens, to the Village Inn in Manhattan, where Pearl Bailey championed him and Bob Hope invited him to sing in his show at the Paramount Theater. After Bennett finished his number, Hope joked, “Well, I was getting tired of Crosby anyhow!”—another remark with more significance than intended. For two decades, Bing Crosby had ruled the mainstream of pop singing, engendering countless imitators and a genuine rival in Sinatra, all of them casual baritones. Bennett was a tenor and “casual” was not in his makeup.