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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 "Boulevard of Broken Dreams" and signed him to the label. 

Bennett's first hit, "Because of You," topped the charts in September 1951, succeeded at number one by his cover of Hank Williams' "Cold, Cold Heart." Following another five chart entries over the next two years, he returned to number one in November 1953 with "Rags to Riches." Its follow-up, "Stranger in Paradise" from the Broadway musical Kismet, was another chart-topper, and in 1954 Bennett also reached the Top Ten with Williams' "There'll Be No Teardrops Tonight" and "Cinnamon Sinner." The rise of rock & roll in the mid-'50s made it more difficult for Bennett to score big hits, but he continued to place singles in the charts regularly through 1960, and even returned to the Top Ten with "In the Middle of an Island" in 1957. Meanwhile, he was developing a nightclub act that leaned more heavily on standards and was exploring album projects that allowed him to indulge his interest in jazz; notably 1957's The Beat of My Heart, on which he was accompanied mainly by jazz percussionists, and 1959's In Person With Count Basie and His Orchestra. By the early '60s, although he had faded as a singles artist, he had built a successful career making personal appearances and recording albums of well-known songs in the manner of Frank Sinatra.