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Thu Oct 22 2026 at 06:30 pm to 09:30 pm UTC-07:00

The Westside Sheiks, live at The Alley-Oop

  • The Alley-Oop · Santa Cruz
Preacher Boy Publisher / Host Preacher Boy
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The Westside Sheiks, live at The Alley-Oop
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The Westside Sheiks play "Alternative Tin Pan Alley for The New Weird America." The duo features Jon "Captain Ahab" Dryden on piano and Christopher "Preacher Boy" Watkins on National guitar and vocals. The Sheiks cite as influences everyone from Mose Allison, Leon Redbone, and Dr. John to Victoria Spivey, Jelly Roll Morton, and Leroy Carr & Scrapper Blackwell. The Westside Sheiks have three albums out on Coast Road Records, with their most recent being Soline. Their sound has been described as “Lemmy singing with Art Tatum for a set of ragtime jazz, vintage blues, and original Americana.” The Westside Sheiks album Eleven Rounds won “Best Roots/Blues Album” at the Manifesto Awards.

About Jon Dryden
Jon Dryden is a pianist, keyboardist, and composer. He graduated from the Berklee College of Music and moved to Brooklyn, NY, where he spent two decades performing and recording with Norah Jones, David Byrne, Regina Carter, Lenny White, Paula Cole, Madeline Peyroux, Sara Ramirez, and many others. He has released two piano trio albums, both recorded in New York: Memento Mori (2020) and Trio (2022). Trio was produced by GRAMMY-winning singer-songwriter Jesse Harris. His latest record, Some of My Lies Are True, was released in June 2026. Jon Dryden is currently an adjunct professor and lecturer of jazz studies at San Jose State University and Santa Clara University.

About Preacher Boy
Preacher Boy mines the dark edges of contemporary blues and Americana with his signature raspy voice, virtuoso National slide guitar playing, and darkly poetic lyrics. Recognized as “the godfather of alt blues,” this relentlessly pioneering artist continues to both honor and extend the country blues traditions that inspire him, while infusing his sound with influences ranging from punk rock to political folk. Of his boot-pounding live performances, Santa Cruz’s Good Times had this to say: “As he beats his long leather boot, four to the floor, his National steel guitar slides and spits a devious storm of gothic Americana and gritty country blues.” Melody Maker described his sound as: “Country blues that marry Nick Cave, Robert Johnson, Woody Guthrie and Tom Waits,” and legendary music publication MOJO declared that “Preacher Boy is a songwriter of startling originality.”
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The Alley-Oop, 320 Cedar Street,Santa Cruz, California, United States

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