Dale worked the New York club circuit with the pianist Bob Gaddy. He also was a frequent session guitarist in the New York studios, playing on all four of Dupree's 1956–58 sessions for RCA's Groove and Vik subsidiaries, and on the best known Dupree LP, 1958's Blues from the Gutter, for Atlantic. His playing on that album inspired Brian Jones of The Rolling Stones.
Dale made most of his best sides as a leader when the decade turned from the 1950s to the 1960s. For Glover Records he recorded the party blues "Let the Doorbell Ring" and "Big Muddy" in 1960, then revived Stick McGhee's "Drinkin' Wine-Spo-Dee-O-Dee" in 1962 on Atlantic. He died in New York in May 2010, at the age of 87.