Tracking Down “Windy City”
Following the trail of Kenny Baker’s “Windy City” through recordings, memories, and the friendships that keep the tunes alive.
Lately, I’ve been tracing the path of Kenny Baker’s tune “Windy City” — a title that seems simple until you start digging into the details.
Kenny recorded it twice with Josh Graves — both times listed as “Windy City” — and later revisited the tune on his Spider Bit the Baby album under the same name. In many discographies, and in Alison Krauss’s recording, the piece appears as “Windy City Rag,” though in Kenny’s original releases and recording credits it’s often simply “Windy City.”
Interestingly, the title “Windy City Rag” helps distinguish it from her later 2017 album Windy City, which features Alison’s rendition of a completely different song — the bluegrass classic “Windy City,” written by Bobby Osborne and Pete Goble. The shared title across these, at first seemingly unrelated works, often adds to the confusion.
What I’ve been trying to track down is whether there’s an earlier recording of Kenny playing “Windy City” — perhaps a solo cut or studio take that predates the sessions with Josh. To follow that trail, I called Ronnie Eldridge, a close friend of Kenny’s and the person who first made it possible for me to visit him years ago. Ronnie arranged those first visits — the ones where I got to sit in Kenny’s home, show him my fiddles, record some video, and take a few photos while we talked about music. Kenny was in good spirits then — relaxed and generous with his stories.
Later, after his health declined, I returned again — this time to the hospital, where I played his own version of “Pass Me Not” for him in the critical care unit. Two very different moments, but both reminders of what it means to stand close to the music that shaped you.
I haven’t heard back from Ron yet, but if anyone might remember the earliest session for “Windy City,” it’s him. Sometimes tracing a tune isn’t just about discographies or liner notes — it’s about memory, friendship, and the quiet persistence of the melodies that refuse to be forgotten.
1️⃣ Kenny Baker & Josh Graves — “Windy City”
From Tennessee–Kentucky Favorites (Montana Country, 1987)
Featuring: Charlie Cushman (banjo), Josh Graves Jr. (bass), Josh Graves (dobro), Steve Whitter (dobro), Burt Hoffman (drums), Kenny Baker (fiddle).
2️⃣ Kenny Baker & Josh Graves — “Windy City”
From Flying South (Ridge Runner, 1986)
Featuring: Don Van Winkle (banjo), Stephanie Macchia (bass), Kenny Baker (fiddle), Marty Javors (guitar), Hank Harrison (mandolin), Slim Richey (producer), Buck Graves (dobro).
3️⃣ Alison Krauss — “Windy City Rag”
From Two Highways (Rounder Records, 1989)
4️⃣ Osborne Brothers — “Windy City”
From Bobby & Sonny (Decca Records, 1972)
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Written as part of the Reflections Series for The Fiddle Canon Project — exploring the living traditions, histories, and voices within American fiddle music.
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