Their first three singles were all arranged by frequent Winley collaborator Davey Clowney, better known as Dave "Baby" Cortez, and all three—"So Strange" / "Love No One But You", "Please Let Me Love You" / "I'm Falling in Love" (both 1957) and "The Plea" / "Oh Baby" (1958)—made the outer reaches of the national Pop chart, and generated considerable New York interest.
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Under a different line-up, The Jesters reached #110 on the Billboard chart in 1960 with a version of The Diablo's "The Wind" backed with "Sally Green".