Tyler Stoddard Smith’s first encounter with prostitution came as a young boy, when his parents drove him around Houston’s red-light district to soothe his chronic insomnia. Fortunately, Whore Stories, his funny, bawdy anecdotal study of the sex trade, is anything but sleep-inducing.

The book germinated when, while kicking around ideas, Smith and his agent discovered that Maya Angelou had been a prostitute. Smith wondered who else might share that background. “I like the notion behind Eminent Victorians,” he says, “of taking people that we normally put on a pedestal and showing more of the coarse humanity to them.” In his new book, he knocks plenty of luminaries off their pedestals, from the Roman Empress Messalina to modern-day rent boys Cary Grant and Clark Gable and Brady Bunch ingénue Maureen McCormick. His most surprising find? Hollywood he-man Steve McQueen performed in Havana sex shows.

Smith, whose humor and short fiction have appeared in McSweeney’s and Esquire, keeps the tone loose-limbed and lightly comic, for which he won plaudits in a Kirkus review that called the book “good, dirty fun.” His favorite stories concern the shaggy-dog antics of figures like Mary “Bricktop” Jackson, a flame-haired New Orleans strumpet who, along with a comrade who had a steel ball where his hand used to be, practiced a devilish criminal ruse known as the “buttock and twang,” which involved descending on vulnerable johns when their pants were down.

But Whore Stories—classified as historical “reference,” though it’s not quite school-library material—also unearths some class acts amid the two-fisted streetwalkers: the brilliant Ming Dynasty courtesan/poetess Liu Rushi; the French dramatist Jean Genet, who sold his body to English sailors for bread and sardines; and the “magical mystery whores” who populate mythologies, from the Whore of Babylon to the legendary Japanese Jorogumo, the shape-shifting “prostitute spider” who enticed and then devoured unwary samurai.

“I’m a history and trivia buff,” Smith says. “I’m really interested in trying to make connections between times and place”—ideally, connections that yield his preferred brand of “high-falutin’ entertainment.” And so the story of Phryne, the legendary prostitute who scandalized ancient Athens with her naked beach frolics, which leads to an amusing profile of Diogenes, the philosopher who lived in a clay jar, ate rancid onions and annoyed his fellow Greeks by showily searching everywhere for an elusive honest man.

Smith brings his genial learnedness to this smorgasbord of quaint, curious lore couched in hip, jazzy prose and caustic wit. His favorite targets are the hypocrisies of the proud and pompous, the Jimmy Swaggarts of the world, who condemn sex in public while diddling with call girls in private. Threading through his barbed humor is a broad empathy for the lowest—and most human—of common denominators, but just about anything is fair game, including Bob Dylan’s “jaundiced gnu” visage.

Along with being featured in Kirkus’ Best Indie Books of 2012, Whore Stories has garnered Smith more glowing reviews, readings in Houston and Austin, and the praise of people whose opinions matter to him. He’s found it a gratifying diversion from his day job as a freelance ad copywriter. (“All writing is good writing,” he gamely opines.) Now, he’s hard at work on a dark novel about cutthroat conflict and suicide in yet another depraved subculture—Little League Baseball.

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