Shakey Jake: The Soul of the Streets and the Soundtrack of Ann Arbor

June is Black Music Month and I want to spend Fridays this month honoring the music artists that helped make me and Ann Arbor as a whole better. When you think of the sound of Ann Arbor, it’s impossible not to hear the footsteps, laughter, and unforgettable presence of Shakey Jake Woods.

If you frequented downtown Ann Arbor during the 70s, 80s, 90s or early 2000s you where sure to see a his familiar face. He wasn’t just a musician—he was a living, breathing embodiment of the streets downtown Ann Arbor. With his bold sunglasses, flashy suits, and ever-present guitar (even when it wasn’t plugged in), Shakey Jake brought rhythm and soul to the sidewalks of our city. Born in Little Rock, Arkansas in 1925, Jake made Ann Arbor his permanent stage in the 1970s, performing blues and jazz riffs in his own unique style—sometimes more silent performance art than traditional busking, but always unforgettable.

What set Jake apart wasn’t technical perfection. It was spirit. It was culture. He stood as a reminder that Black music isn't just something you listen to—it's something you live. And Jake lived it every single day. Whether he was waving to students on the Diag or posting up outside Blimpy Burger, he was creating a living, looping soundtrack of Black joy, struggle, and self-expression.

As a high school student at Community High during the early 2000s, I was lucky enough to have the chance to have long talks with Jake. We spoke about life, music, being a black person in Ann Arbor and how Ann Arbor had changed over the years. He was a gentle soul who loved Ann Arbor just as much as we love him.

During Black Music Month this June, we honor Shakey Jake not just as a local legend, but as part of a national lineage of Black musicians who turned everyday sidewalks into sacred stages. He may have passed in 2007, but Jake’s legacy still grooves in every street performer, every spontaneous jam session, and every Ann Arbor townie bold enough to dance to their own beat. Share your Shakey Jake story below and let us know how you remember Jake!

Want to know more about the legends who shaped Ann Arbor’s music scene? Follow @AnnArborHub and stay tuned for our Black Music Month series.