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Calysta Cheyenne, jazz vocalist, mid-dance in a tailored suit and heels
Calysta CheyenneBooked 05.22.26 · Barrel RoomJazz vocals · Great American Songbook

Live music · Portland, Oregon

Calysta Cheyenne

Calysta Cheyenne sings jazz standards from the Great American Songbook, which is a polite way of saying she can make a room full of wine drinkers go quiet on a Saturday. She has been singing that catalogue across Oregon since she was a teenager, trained for nearly two decades with vocal coach Ken Orsow here in Ashland, then studied vocal jazz at Berklee College of Music. Ella Fitzgerald, Julie London, Peggy Lee and Billie Holiday are the influences, and you can hear all four by the second song. She lives in Portland now and drives down anyway. Draw your own conclusions about the pizza.

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Calysta Cheyenne at Resistance Wine Company | Ashland