‘Classic Showbiz’ Tells the Fascinating Story of Forgotten Gay Comedy Pioneer Ray Bourbon

Pod-Canon is an ongoing tribute to the greatest individual comedy-related podcast episodes of all time.

Comedy historian Kliph Nesteroff’s ambitious history of American comedy The Comedians is essential and invaluable in no small part because it does not profess to be authoritative or exhaustive. With a subject as vast and deep as American comedy, how could it be? Indeed, its most fascinating passages generally chronicle not the bold-faced legends who famously catapulted the medium forward, your Andy Kaufmans and Lenny Bruces and Richard Pryors, but rather the semi-obscurities who had been forgotten despite the bizarre and colorful nature of their lives and careers before Nesteroff helped bring them back to life with his words.

Ray, or Rae Bourbon, a comedian and cabaret performer born Hal Wadell sometime in 1892 (like the lady he portrayed for fun and profit, he wasn’t about to be honest or candid about his age or real birthday) whose risqué comedy screamed his effeminate homosexuality from the mountaintops at a time when homosexuality was more often a secret barely whispered about, ranked as one of the most fascinating obscurities in The Comedians. With his new mini-series Classic Showbiz, Nesteroff brings Bourbon’s too-strange-for-fiction life story to an audio medium that allows fans of Nesteroff’s work to actually hear what they could previously only read about, and it makes a huge difference. There’s a musicality and a breezy assurance to Bourbon’s delivery and persona that undercut the hack nature of his material.

In his winking, leering, double and single entendre-laced comedy routines, Bourbon shamelessly embodied the stereotype of the lisping, quipping, sex-obsessed screaming queen, but there’s an unabashed joy to his comedy and particularly to his self-presentation that betrays defiant, rebellious pride. The podcast describes Bourbon as possibly the most arrested and imprisoned comedian of all time. In that respect, he’s like the DMX of old-school queer comedy. Bourbon was outrageous onstage, in drag or out of it, but Nesteroff establishes that Bourbon was even more outrageous in what could charitably be described as his “real life,” although Bourbon had such difficulty delineating between fantasy or reality that it’s hard to know where the act left off and the man (or woman) began.

Though a consummate outsider by virtue of both his flamboyant homosexuality and personal eccentricities, Bourbon inherited over a million dollars. Bourbon’s inherited fortune funded his obsessions and idiosyncrasies, from self-releasing comedy albums teasing that the female impersonator may or may not have had a male-to-female sex change operation in Mexico (the subtly titled Let Me Tell You About My Operation) to acquiring and feeding dozens of cats and dogs. At the worst of his hoarding, Bourbon had over seventy cats and dogs. In keeping with the predictably tragic arc of a man who lived and worked as a gay man at a time when doing so simply wasn’t allowed, and suffered the consequences, Bourbon’s pets were eventually taken away from him and used for experimentation in a series of events directly leading to his arrest and imprisonment.

The emergence of the gay rights movement and out gay artists in the 1960s and ’70s might have given Bourbon’s career a boost if he didn’t embody sometimes painful stereotypes for gay audiences the same way that Stepin Fetchit’s screen appearances did for Black Americans. It also did not help that Bourbon spent the final years of his life in jail convicted of being an accomplice to the murder of the kennel owner who disposed of his animals before dying in jail in 1971.

Bourbon paid a terrible price for being out and gay when times angrily demanded that he be closeted and deeply ashamed in the form of harassment, arrest and incarceration, but Nesteroff also establishes that, like seemingly everyone in The Comedians, he was also enormously self-destructive, his own worst enemy in so many ways.

Classic Showbiz is executive produced by Marc Maron, who has long championed Nesteroff’s work. The mini-series plays like a winning companion piece to WTF. Maron is a comedy historian in his own right;  he just happens to attack the subject from the perspective of a podcast interviewer rather than a dude writing books about comedy history.

This covers an awful lot of ground in less than thirty minutes but there’s clearly also a lot of ground left to cover. Nesteroff has performed a valuable service in bringing Bourbon’s curious, poignant, and both tragic and triumphant life back into public view. Now it would be great to see that story explored in a feature-length documentary or book-length biography. Alternately, Bourbon would be a great role for an actor or actress, or, alternately, a one-man or one-woman show. Because heaven knows, when it came to gender, and so much else, Bourbon was a big believer in always keeping them guessing.

Nathan Rabin is the author of five books, including Weird Al: The Book (with Al Yankovic) and the recently released Ebook “Short Read”, 7 Days In Ohio: Trump, The Gathering of The Juggalos And The Summer Everything Went Insane.

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