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Benson started out at the age of eight as a singer in his native Pittsburgh, and made his first professional recordings at 11. He took up the guitar in his teens, and when he formed a rock group, he played a guitar his stepfather had built for him. Listening to records by Charlie Parker, Charlie Christian and Wes Montgomery got him into jazz, and was playing for organist Jack McDuff while still a teenager. He formed his first jazz group in 1965, and was discovered by the legendary record producer John Hammond. He did several albums of his own, and also recorded with Miles Davis and others. In the late 1960s, he was seen as a possible successor to Wes Montgomery after the latter's sudden death. Noted jazz record producer Creed Taylor recorded him for A & M and CTI, but after he went to Warner Brothers, he concentrated on his singing, and had a Top Ten crossover hit with "This Masquerade." After a number of pop-jazz albums, he showed he was capable of a more straightahead style with the standards album "Tenderly," an album with the Count Basie Orchestra, and as a guest on the Jon Hendricks album "Freddie Freeloader." He continues to record and perform in both pop and straight-ahead jazz styles.