Westley Heine Credit: Courtesy the artist

Westley Heine never dreamed of singing for change on the streets of Chicago but life sometimes offers only stark choices. Getting by as a musician, artist, or writer is uphill barefoot through snowdrifts on a good day. Add a recession, a relationship going sour, some substance abuse, and a generous helping of self-doubt and few would bet on a guy’s chances. Yet Heine perseveres. Grounded in street-level observation and faith in his muse, his story isn’t always pretty but rings that much more true for its rough edges.

Busking Blues opens in early 2010s Chicago as the Great Recession is in full swing. Heine leaves a longtime girlfriend after their volatile relationship becomes untenable and finds himself homeless and underemployed. Sporadic shifts at a supermarket situated on the dividing line between the mostly demolished Cabrini-Green housing projects and upscale Old Town aren’t enough to pay rent on his own place, so he decides to try his hand at playing music on the streets while squatting on friends’ couches. 

When I call Heine in LA—where he’s moved with his wife for a change of scenery and to escape the harsh midwestern winters—we talk a lot about the line between fiction and memoir. Both Busking Blues and his 2021 chapbook, 12 Chicago Cabbies, tell stories that Heine experienced. The only changes or enhancements, according to Heine, are a few altered names; most other inaccuracies, he chalks up to the limits of memory. As a writer who’s never leaned much on imagination, Heine’s approach is familiar and welcome to me. There’s little the human mind could conjure to match the chaotic randomness of lived experience.

Heine is a heart-on-his-sleeve seeker. Taking lessons from veteran buskers, seasoned grocery store coworkers, and former professors seriously, his path towards life lived for art is a treacherous one but always tinged with beauty and hope. No matter the obstacles or reversals, he keeps saying yes to any opportunity that comes his way. Sometimes that means a few days cat-sitting for a friend with access to a shower and a comfortable bed; other times it’s a nebulous relationship with an older woman that rides the line between chaste friendship one day and being stalked by her the next. It all adds up to a crazy quilt of urban experiences that a self-described country boy from Wisconsin could scarcely have imagined.

The thing Heine keeps coming back to in our talk is how much of the things that happened to him were the result of chance. “As a person who has a pretty scientific worldview I found it unsettling during the busking period because I found myself living on luck, the chance encounters on the grid. To start thinking in terms of fate, karma, superstition was troublesome to me.”

Busking Blues: Recollections of a Chicago Street Musician & Squatter by Westley Heine
Roadside Press, paperback, $15, 274 pp., magicaljeep.com

The starkest case of kismet comes toward the end of the book. I’d assumed it was poetic license, but Heine tells me otherwise. “I intended to win that nice guitar and then I did. This freaked me out and I started going off the deep end with mind over matter/ free will concepts. Then, I lost the guitar in the taxi. This really happened as well. Easy come easy go before it was returned to me by the driver. Should I have taken this to mean that everything is random and meaningless?”

In between relating anecdotes, Heine grapples with how to tell his story. “If you just say bleakly what happened is it art or reporting the news? Is journalism or documentary an art or is it not? If the work is pure fantasy does it do anyone any good in the real world? Does art have to have a moral? Or is it better to have some moral ambiguity?” 

book cover for Busking Blues by Westley Heine
Credit: Courtesy Roadside Press

While he may not have arrived at a definitive answer on how to present his experiences in his writing, I responded most to the parts of his book which present his life with little commentary or philosophizing. A problem for any writer plumbing everyday life for material is that there’s rarely a clear narrative arc. But a story needs a beginning, middle, and end so we must improvise or invent. Heine’s solution is a dream sequence that flashbacks much of the novel’s main points and adds a heaping dollop of spiritual wondering. During our phone interview, he freely admits to making this part up. I wish he hadn’t. This tendency to make sense of or wrap up lived moments in a neat bow aren’t necessary when the anecdotes are strong and can resonate under their own power, without the addition of “morals” or “meanings.”

To my way of thinking, art works like a mirror pointed outward at the viewer. You take your life and that of those around you and tell it with whatever means at your disposal, be it a pen, a guitar, or a brush. You watch and listen to your environment and put it into words, notes, and images and your audience will see themselves rather than the artist. When Westley Heine writes about singing blues at a CTA stop, working the deli counter at Jewel, or riding the Green Line to the west side to sleep in his practice space, it’s a life and locales I recognize. There’s no need to explain or grasp for any larger lesson. But I also understand well the doubts that creep in at low moments, voices that whisper all your efforts are in vain. That’s a struggle that never goes away. Perhaps that’s the true subject of this vivid and engaging ramble through the Chicago of a decade ago.