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Miles Davis: The First Playboy Jazz Festival

The trumpeter's quintet played 'So What' at the 1959 concert event

Marc Myers's avatar
Marc Myers
Nov 14, 2025
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The first Playboy Jazz Festival was held August 7-9, 1959 at Chicago Stadium. The venue was an indoor arena built in 1929 and, at the time, was the largest in the world with maximum seating of 26,000. The building was demolished in 1995.

Jazz for Playboy magazine’s founder Hugh Hefner was an end to a means. It’s unclear whether he actually liked jazz, un…

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