REVIEW: The Midnight Special by Colin Asher
Dmitry Samarov on Asher's new book about how the prison industry shaped music, in which Asher is "a careful and sympathetic observer who does his homework."
I’ve been a fan of Colin Asher’s since reading his Nelson Algren biography seven years ago. Algren is a writer who’s foundational to my understanding of Chicago, the city I live in and love, as well as a formative literary influence, but Asher’s book taught me many new things about a subject I thought I knew pretty well. When he wrote me about his forthcoming book, The Midnight Special, I was happy to receive an advance copy.
We taped a conversation after I finished reading to help me fill in gaps before I wrote this review.
In the acknowledgements at the back of his book, Asher recalls how during COVID lockdown his partner, a public defender, was forced to help her clients navigate New York’s notorious Rikers Island prison remotely from their Brooklyn home. In the next room, Asher was teaching English classes via Zoom, listening to a lot of jazz to stay sane. One of his go-to’s was Elmo Hope’s 1963 LP, Sounds from Rikers Island. He’d owned it for years but the overheard conversation from next door now lent it new resonance and context. Hope would become one of the five main subjects profiled in Asher’s unusual, affecting study of the impact of incarceration on some of the most popular music produced in this country.
The first chapter sketches out the star-crossed life of Huddie Ledbetter, an itinerant laborer in the South, who, through the poor luck of being born Black in America, endured repeated stretches behind bars. His famous stage-name, Lead Belly, comes with a conflicted etymology, possibly originating from a play on his surname, or for getting shot in the stomach, or from a capacity for drink. A prolific singer, songwriter, musician, and interpreter and gatherer of traditional folk tunes, he set the template for the continuing contradictory relationship between this country and its Black performers—celebrated for their obvious talent and subjugated for their perceived menace and lawless nature.
The father-son ethnomusicologists John and Alan Lomax singled out Ledbetter during their tours of Southern prisons, then used him as a kind of conduit to discover other talent behind bars. Even as his fame grew on the outside, his association with the carceral system preceded him wherever he went, sometimes serving as a kind of advertising to draw onlookers the way a carnival barker might lure marks on the midway. A jailbird who sang his way to freedom.
He kept getting arrested, often under dubious circumstances, through much of his life and his story is a kind of grim foreshadowing of Asher’s final subject, Tupac Shakur, a man whose songs prophesied his own descent into lawlessness and tragedy.
The second chapter deals with Elmo Hope, a talented jazz pianist undone by his run-ins with the police before succumbing to heroin addiction. A decidedly lower-key personality than Ledbetter, Hope’s story is nevertheless similarly skewed by the structural racism of the country he had the misfortune to be born in. The overarching Damoclean sword hanging over his career was an inability to secure a cabaret card due to his criminal record—a New York license enabling musicians to make a living in nightclubs in the city. Not having a cabaret card was tantamount to being blacklisted and the cruel catch-22 of ex-offenders being denied one virtually guaranteed their eventual need to reoffend. It was a regulation calculated to make Black musicians’ lives much more difficult than they already were. By the time it was repealed, Hope was dead, a broke addict at 44.
Chapter three is an outlier in that its subject is white and served no prison time. Nevertheless, Johnny Cash’s ties to prisons can’t be denied. Many of his most successful songs detail criminal life and some of the best-selling albums were live recordings made within houses of correction. He advocated for inmates rights for many years, even taking aspiring songwriters on tour after their release. But there’s no way not to see how Cash’s experience stands in stark contrast to Black musicians with similar histories of substance abuse and high-risk behavior. Even when he was busted for smuggling huge quantities of amphetamine pills from Mexico, he got off with a slap on the wrist. The system was rigged in his favor no matter how far he pushed its strictures.
As the most widely-known of Asher’s subjects, Cash is also in a way the least compelling. His story has been so often documented in words, sounds, and images that even a writer as meticulous as Asher can only present him as a kind of mythical archetype whose shadow obscures lesser known but no less memorable figures. Of the two aspiring singer-songwriters Cash sponsored that Asher writes about, the diametrical outcomes of Glen Sherley’s and Harlan Sanders’ post-prison lives are instructive. One wasn’t able to maintain the straight and narrow, while the other thrived. The reasons are too many and varied to be reduced to an if/then, which underlies the danger of separating men from society and then expecting them to jump right back into line when their exile’s term is up.
The fourth chapter is dedicated to perhaps the most baffling of Asher’s five heroes. Ike White came from a supportive musical family but spent most of his early adulthood incarcerated for killing a shop owner in Oakland during a robbery gone sideways. Preternaturally gifted on any musical instrument he picked up, and charming enough to convince men to help him and women to fall for him, White nevertheless squandered the many chances afforded him. White was mentored by Spade Cooley, a once-famous country musician who murdered his wife and was serving a life sentence. An inveterate liar, White admits in a rare moment of candor that his time in prison made him always read whoever he came into contact with to gain whatever advantage could be had.
Tracked down years after gaining his freedom, old supporters found a man living under a variety of assumed names, spinning tales that only passed water in his own reality. Seemingly happily married to a Russian woman who’s clearly enthralled with him, White waits for her to leave the house one day and takes his own life. Nothing about the man adds up.
For those who want to know more about White, I’d recommend Daniel Vernon’s 2021 documentary, The Changin’ Times of Ike White. It’s briefly cited in Asher’s book.
Tupac Shakur rounds out the book in a chapter that feels like an inevitable result of the stories that preceded it. It begins in utero as Shakur’s mother stands trial for activities as a member of the Black Panthers. She is acquitted after serving as her own lawyer but the years that follow are a seesaw of triumph and failure, as she works as a paralegal while continuing her political commitments, but then falls victim to crack addiction. Her son grows up self-sufficient and introspective. He aspires to be a Shakespearean actor and excels at school, but after being beaten by two white cops just as his debut album is released, Shakur is gradually transformed into the kind of outlaw he once disdained. It’s a tragic story whose ending most people living in this country in the past forty-fifty years could have predicted without thinking too hard.
If this country was better it wouldn’t be so easy.
Asher doesn’t prescribe any solutions to the endemic and intractable problems that force talented people in this country to have to express themselves from within cages. He’s not a proselytizer but rather a careful and sympathetic observer who does his homework and lets his readers come to their own conclusions. The fact that any of the beautiful sounds created by these men managed to float free from the ties that bound them is some kind of miracle. Asher’s book is an unexpected gift that reminds us of what we’ve gained from their suffering.
—Dmitry Samarov writes dog portraits and paints book reviews in Chicago, Illinois. His website is old enough to drink.
A terrific review of a very important book.
This is great, Dmitry!