When searching for explanations as to why Roddy Doyle's Oh, Play That Thing—the second installment of the trilogy that began with the ferociously gripping A Star Called Henry—turned out to be such a crushing disappointment, the best place to start is at the back of the book. In his acknowledgements, Doyle thanks an eclectic two-page list of authors who inspired his portrayal of American urban life in the mid-'20s and onward, thanks to their key works on jazz, immigration, gangsterism, and the neighborhoods of New York's Lower East Side and Chicago's South Side. The list goes far in explaining why Oh, Play That Thing feels more imitative than imaginative: It creates a falsely aestheticized America with shopworn images, overripe street language, and unlikely encounters with historical figures. A Star Called Henry sharply evoked the poverty and brutality that gave birth to an IRA hoodlum, but Oh, Play That Thing abandons its predecessor's realist grit for a broad riff on the Jazz Age.
Left fleeing his IRA paymasters at the end of the last book, the resilient, resourceful Henry Smart ships off to Ellis Island with other poor immigrants in 1924, but he plans to take advantage of the land of opportunity sooner rather than later. Bouncing from job to job, Henry turns a humble gig as a sandwich-board man into an entrepreneurial venture that includes sneaking prohibited liquor into New York speakeasies, but the local mobsters don't like him infringing on their territory. Though tough and irascible as ever, Henry recognizes mortal danger when he sees it, so he takes off for Chicago to stake a new claim, and finds a city intoxicated by the jazz scene. In the book's biggest—though not most improbable—coincidence, Henry stumbles into a South Side "black and tan" (an integrated nightclub), where he befriends Louis Armstrong, who brings him on as a manager/bodyguard. In turn, Henry recruits the frequently dead-broke Armstrong into helping burgle the homes of the city's wealthy elite, including Marshall Field's estate.
Oh, Play That Thing comes to life when Doyle describes the hothouse atmosphere of the jazz clubs and the sheer excitement of hearing Armstrong's revolutionary trumpet, which he blasts through bleeding lips and hard times. But getting there takes some doing: The New York scenes are a chaotic, exhausting flurry of activity, hampered by confusing relationships and incomprehensible stretches of rat-a-tat dialogue with lingo that Doyle seems to have invented from whole cloth. Provided that readers can roll with Henry's outlandish partnership with Armstrong, the book improves once the action moves to Chicago, but even then, the illusion is spoiled by a run-in with Henry's past that defies any reasonable suspension of disbelief. Henry is a human pinball who gets booted back to Harlem and beyond in the final third of Oh, Play That Thing, but the prospect of further adventures doesn't seem worth any anticipation.