There are so many aspects of life, culture, law, crime, and sociology connected to the U.S. prison system that billions of words in books and reports have spilled across forests’ worths of pages examining them.

But one connection has resonated into greater culture: Music. Journalist/author Colin Asher goes deep into the bond in The Midnight Special: The Secret History of Prison Music in America (336 pp., $29.99, W.W. Norton & Co.).
Asher takes a unique approach by focusing on five men—and five specific records—who either wrote and recorded music while in prison or about their prison experiences. They are bluesman Huddie “Lead Belly” Ledbetter, jazzbo Elmo Hope, country icon Johnny Cash, R&B/funkateer Ike White, and rapper Tupac Shakur.
Asher details the creation of (in order of list above) records The Midnight Special and Other Prison Songs (1940); Sounds From Rikers Island (1963); At San Quentin (1969); Changin’ Times (1977); and Me Against the World (1995). But also provides a wider biographical arc for each artist, including the reasons for why they landed behind bars.
Two of the chapters are of particular interest. The story of the supremely talented but self-destructive Ike White—a name mostly unknown except to the hardcore ‘70s R&B/Funk fans—is worthy of its own movie. And actually was the subject of the 2019 doc The Changin’ Times of Ike White. Changin’ Times which managed to be both behind the times and ahead of it in various ways.
The other belongs to Lead Belly. While much has been written about him over the years, Asher manages to go deep into the nooks and crannies of his life, and his in-and-out of incarceration journey. He also examines the relationship between Lead Belly and noted musicologists John and Alan Lomax (forebears of the late Houston Press music editor, John Nova Lomax) who “discovered” Ledbetter and brought his music to the world.
The three had a very symbiotic relationship, though Asher details the very paternalistic tone and treatment that especially John Lomax laid on Lead Belly—and often in a way that, while reflective of the times, would be shocking today.
As when Lead Belly preferred to perform in a suit, but Lomax insisted he appear in worn overalls or even prison garb (long after he’d been freed), playing up the “dangerous murderer” angle.
There’s local reference in Asher’s pages about Lead Belly serving time at the Imperial State Prison Farm in Sugar Land. And of course, Houston appears in perhaps Lead Belly’s best-known song that also gives this book its title.
Lead Belly names names:
If you ever go to Houston, boys you better walk right/And you better not squabble, you better not fight/Benson Crocker will arrest you, Eddie Boone will take you down/You can bet your bottom dollar, that you’re Sugarland-bound.”
And later, rockers Creedence Clearwater Revival had a big hit with slightly altered words:
“If you’re ever in Houston/Well, you better do right/You better not gamble/There, you better not fight, at all/Or the sheriff will grab ya/And the boys will bring you down/The next thing you know, boy/Whoa, you’re prison bound.”
As four of the five men profiled here are Black, Asher has much to say about how the judicial and prison system has either failed or been stacked against persons of a darker hue. He cites many examples in their stories of how similar offenses committed by a white person (and especially in the South) would go unremarked or unpunished.

And for all his “rebel outlaw” persona over the decades, Johnny Cash’s illegal antics only landed the Posterior in Black a single night in a jail cell. Though he committed plenty of (though relatively minor) offenses where a Black man wouldn’t have gotten a pass.
Yet he’s intricately connected in memory to prisons for the crackling, live albums he recorded at Folsom State and San Quentin. Asher recreates the delicate negotiations that brought Cash, his band, and various other acts to the stage and how officials were with good reason worried that they might have a riot on their hands.
Yet, Cash genuinely stood for prison reform for most of his life and even took one Folsom-incarcerated performer/songwriter, Glen Sherley, under his wing after he was released. Cash had already performed Sherley’s “Greystone Chapel” during the concert, shocking the inmate.
“Trying to write a definitive history of American prison music would be quixotic. This book isn’t that,” Asher writes in the introduction. Adding that the individual stories “have something distinct to say about the ways that policing and incarceration, have shaped our musical culture—affecting our perception of an artist’s work, choosing who is able to perform, record, and tour, and influencing the development of musical styles.”
Thus, The Midnight Special succeeds in several fronts in being a book about artists, music, the creative process, and how one of the worst places a person could end up in relates to it all.

Bonus Book Review!
There’s a trend in recent years for music book publishing that views an artist directly through the lens of their actual music. Thus, we have titles like Stevie Nicks in 50 Songs by Annie Zaleski, Bruce Springsteen: The Stories Behind the Songs by Brian Hiatt, and The Clash: All the Albums, All the Songs by Martin Popoff.
The wide-ranging genre of the blues gets that treatment in The Story of the Blues in 50 Songs by Mike Evans (208 pp., $49.99, Schiffer).
Evans cherry picks selected tracks—both well-known and more obscure—from Ma Rainey’s 1924 release “See See Rider Blues” to Muddy Waters’ 1954 “I’m Your Hoochie Coochie Man” to Stevie Ray Vaughan’s 1983 “Texas Flood” up to 2021 with Christone “Kingfish” Ingram’s “662.”
Along the way we also meet names like Charley Patton, Elmore James Big Joe Turner, Ruth Brown, Howlin’ Wolf, B.B. King, Ry Cooder, Robert Cray, and Gary Clark. Jr. And a whole lotta early musicians who were deprived of sight (Blind Lemon Jefferson, Blind Willie Johnson, Blind Wilie McTell).
Throughout, Evans distills the artists’ life stories into digestible chapters, and the book is lavishly illustrated with photos, collectibles, and ephemera. Bridges chapters cover important record labels, instruments, and incidents, and some artists are the subject of revealing and interesting quote from fellow performers, journalists, producers, and songwriters.
The Story of the Blues makes for a handsome gift book for both the casual and deep dive blues aficionado. And it will surely inspire readers (including this one) to create one amazing Spotify playlist.
