Tony Middleton was born June 26, 1934. Born and raised in Richmond, Virginia and in the mid-1950s, Middleton moved to New York with his mother. He surpassed others with his skills in various sports and started to box as an amateur in his late 20s. In 1952 he joined the 5 Willows, who would later be billed simply as the Willows, as their lead singer and had a hit record titled "Church Bells May Ring" with the group in 1956. He left the band for a solo career in 1957. After 3 songs produced as a soloist, he could not produce a hit song so he moved to Paris, France in 1962. He drew many fans in Paris, France. He then left Paris, France to return to New York and try to make another hit. He came with a powerful, 'You Spoil My Reputation'. Afterward, he made recordings with hit artists including Smokey Robinson, Della Reese and Nell Carter. Later he returned to the Willows and toured a decade with them on the oldies circuit. Although, Tony Middleton did not get that hit that he was dreaming of, he made inspirations for other young jazz singers.