The Troy Street Observer

Mar 14, 1938: Holiday Joins Shaw in Boston

Billie Holiday made history by joining the Art Shaw Orchestra at Boston’s Roseland-State Ballroom.

Art Shaw at Roseland-State advertisement
Billie Holliday (sic) joins the Shaw band, March 1938

An unhappy Billie Holiday left the Basie band in mid-February 1938, and here she was, four weeks later, in Boston and joining the Art (not yet Artie) Shaw Orchestra. That band was working out of Charlie Shribman’s Roseland-State Ballroom, on Mass Ave at Burbank. The brothers Charlie and Sy Shribman, in return for a percentage of the band’s future earnings, were backing Shaw financially and providing rehearsal space for the band during its incubation period.

Shaw’s Orchestra would play at the Roseland-State on Tuesdays and Saturdays, broadcasting over the CBS radio network on Tuesday at midnight, and on Saturday at 6:30—early, before people went out for the evening. Midweek, Shribman booked the band into other New England venues, so someone in New Haven or Springfield could hear the band on the radio on Saturday, and see it on Thursday. It was a successful system for building a band.

Much has been written about the eight months that Holiday remained with the Shaw band, and her departure. Race, predictably, played a big part, but the situation was not helped by the two being signed to different record companies, or by their lack of commercial appeal on the bandstand. After a particularly galling experience at the Hotel Lincoln in New York, Holiday quit Shaw in October 1938.

Billie made only one record with the Shaw band. “Any Old Time” was arranged by Shaw and recorded July 24, 1938.

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