The 50 Essential Sleepy Hollow Artists - WXPN | Vinyl At Heart

As we continue to celebrate 50 years of Sleepy Hollow on XPN’s weekend mornings, we wanted to take the opportunity to honor some of the artists who have played a major role in its sound since 1973. Of course, trying to represent so much music in a finite amount of time is a tall task. But if you’ve listened to the show, you know that some artists just have that tone, that feel, that makes Sleepy Hollow such an enduring part of our weekend routines.

So the Sleepy Hollow hosts and XPN programming staff have come up with 50 artists who represent the considerable breadth of the show’s programming. They range from ’70s singer-songwriter staples like Joni Mitchell and Leonard Cohen, to jazz greats Miles Davis and Billie Holiday, to more contemporary artists who have made their name in the last twenty years–including Norah Jones and Rhiannon Giddens. Essential and eclectic, we hope this list will bring listeners fond memories of where the show has been, and keep listeners excited about how it continues to evolve.

Watch the video playlist of our 50 Essential Sleepy Hollow musicians below, and tune-in to Sleepy Hollow at the top of each hour from Oct 14th through Nov 19th to celebrate 50 years of waking up on weekend mornings with XPN.

Broadcast schedule for Sleepy Hollow essential artists in our video playlist.

Dave Brubeck
Nanci Griffith

Willie Nelson
Tracy Chapman
Ray Charles

Anotonio Carlos Jobim
Tom Rush
Rhiannon Giddens
Chet Baker

Kings of Convenience
Sarah Vaughan
Tom Waits
Yo La Tengo
John Prine

Suzanne Vega
John Martyn
k.d. lang
Bob Dylan

George Winston
Chick Corea
Sufjan Stevens
Cocteau Twins
Nina Simone

John Gorka
Beth Orton
Mark Knopfler
Emmylou Harris

John Coltrane
Patty Griffin
Richard & Linda Thompson

Townes Van Zandt
Alison Krauss
Billie Holiday
Leonard Cohen

Cowboy Junkies
Jeff Buckley
Joan Armatrading
Fleet Foxes
Joan Shelley

Bonnie Raitt
Frank Sinatra
Jane Siberry
Neil Young

Iron & Wine
Joni Mitchell
Nick Drake
Miles Davis
Norah Jones

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