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Shearing
Jazz and pop tended to intertwine when it came to vocal groups, too. The Mills Brothers--John, Herbert, Harry, and Donald--were famous for an act which had only guitar as accompaniment for years, but also recorded with Cab Calloway. Mel Torme's Mel-Tones, whose leader became a widely known and loved pop crooner, as well as one of the most respected voices in jazz, teamed up with Artie Shaw. Sinatra started out with Tommy Dorsey's Pied Pipers.
Even the Andrews Sisters were 52nd Street regulars, and used to hang out at the Onyx Club, fascinated with stream-of-consciousness scat singer Leo Watson; they helped to get him a deal with Decca, though he remained mostly an underground phenomenon, as well as originator of the word "zoot," which he used to holler whenever the mood struck him.
Leo Watson
Pre-Bop
The Snake Pit