Tony Bennett's career has enjoyed three distinct phases, each of them very successful. In the early '50s, he scored a series of major hits that made him one of the most popular recording artists of the time. In the early '60s, he mounted a comeback as more of an adult-album seller. And from the mid-'80s on, he achieved renewed popularity with generations of listeners who hadn't been born when he first appeared. This, however, defines Bennett more in terms of marketing than music. He himself probably would say that, in each phase of his career, he has remained largely constant to his goals of singing the best available songs the best way he knows how. Popular taste may have caused his level of recognition to increase or decrease, but he continued to sing popular standards in a warm, husky tenor, varying his timing and phrasing with a jazz fan's sense of spontaneity to bring out the melodies and lyrics of the songs effectively. By the start of the 21st century, Bennett seemed like the last of a breed, but he remained as popular as ever.
Bennett grew up in the Astoria section of the borough of Queens in New York City under the name Anthony Dominick Benedetto. His father, a grocer, died when he was about ten after a lingering illness that had forced his mother to become a seamstress to support the family of five. By then, he was already starting to attract notice as a singer, performing beside Mayor Fiorello La Guardia at the opening of the Triborough Bridge in 1936. By his teens, Bennett had set his sights on becoming a professional singer. After briefly attending the High School of Industrial Arts (now known as the High School of Art and Design), where he gained training as a painter, he dropped out of school at 16 to earn money to help support his family, meanwhile also performing at amateur shows. Upon his 18th birthday in 1944, he was drafted into the Army, and he saw combat in Europe during World War II. Mustered out in 1946, he went back to trying to make it in music, and he attended the American Theater Wing on the GI Bill. By the end of the 1940s, he had acquired a manager and was working regularly around New York. He got a break when Bob Hope saw him performing with Pearl Bailey in Greenwich Village and put him into his stage show, also suggesting a name change to Tony Bennett. In 1950, Columbia Records A&R director Mitch Miller heard his demonstration recording of "The Boulevard of Broken Dreams" and signed him to the label.