Born Anthony Dominick Benedetto in New York City on August 3, 1926, Bennett was the youngest of three children and was already performing at the age of six. He was called up for the Army in 1944 during WWII. After basic training, Bennett was assigned to the 63rd Infantry Division (the "Blood and Fire" Division) where he served in France and Germany.
While in Europe, Bennett encountered an old friend, and invited him to eat with him. The Friend was black, and an officer from the south suggested that the friend should take his meal in the kitchen. This suggestions was met with language that resulted in Bennett's demotion from corporal to private, and assignment to a unit desinterring mass graves and preparing the bodies for shipment home.
It was while he was in the army that Bennett got his first opportunity to sing -- with a military band. Transferred to special services, he finished the war touring Europe and studied music at Heidelburg University before returning to the U.S. He studied voice under the GI Bill
while supporting himself as an elevator operator. His signature song, "I Left My Heart in San Francisco," was recorded in 1963.