Tony Bennett cut his teeth singing in front of the toughest of audiences as a teenage army-band performer entertaining hardened troops stationed in Europe during World War II. Ever since, he carried the determination and gusto he learned back then through an epic career as America’s consummate crooner. During his initial star-making streak in the ’50s and ’60s, the New York City-born Bennett displayed both a pop singer’s flair for spotlight-seizing spectacle (listen to that soaring, curtain-closing vocal flourish on “(I Left My Heart) In San Francisco”) and a muso’s ear for jazzy improvisation (which blossomed on his supremely swinging albums with Count Basie). Bennett was always in crowd-pleasing mode—you can practically see his smile as he sashays through the big-band orchestration of “The Best Is Yet to Come.” But the natural grit in his voice could also imbue a ballad like Hank Williams’ “Cold, Cold Heart” with palpable melancholy and regret (the singer’s more artistic impulses were channeled into a parallel career as a painter of impressionistic portraits and landscapes). Always faithful to the standards, Bennett’s staunch refusal to conform to trends made him an unlikely hero to alternative rockers and modern pop firebrands alike, with latter-day duet partners like Elvis Costello and Lady Gaga lining up to bask in the eternal charisma that Bennett always exuded so effortlessly. Bennett died in July 2023 at the age of 96.