The Princess and the Whiskheads: A Fable, by Russell Smith, Doubleday Canada, 110 pages, $19.95

Russell Smith is the author of How Insensitive (a novel about Toronto hipsters), Noise (a novel about hipsters who live in Toronto) and Young Men (a hipster-tinged collection of Toronto-based short stories). Smith has spent much of the 1990s chirping the same note, but his trills are catchy and more difficult to sustain than many give him credit for. Smith is following the golden rule of the wordsmith: Write about what you know.

Smith is also nothing if not self-aware, and has clearly been struggling with a tough question -- what next? Eventually, fans will demand something different, Smith will exhaust the city's subcultures, or, God Forbid, he'll outgrow the scenester sandbox entirely.

The result is The Princess and the Whiskheads, a fable about the hipsters of Liralove. The story (set in ye olden days) centres on the hipster minority who populate the kingdom of Liralove, a boho enclave/squat that includes a bar, poetry readings and proto-industrial music courtesy of a machine that's "all cogs and cranks and levers, and rows of glass tubes and metal blades." These ur-beatniks are known as Whiskheads, so-called because they have fine silver filaments threaded through one ear and out the other that glitter "like a cloud of fireflies." Dig daddy-o. These cool cats literally have holes in their heads.

The Whiskheads live in Stjornokh, the capital of Liralove, and when princess Juliana learns they hate everything they think she stands for, she disguises herself and infiltrates their lair. She (of course) falls in love with a Whiskhead named Jan (and vice-versa) but when he discovers her true identity, a riot ensues. There's a sewage system subplot, and a battle between frivolous architecture and industry, but to say more would ruin the surprise.

Smith's Aesop inklings were foreshadowed in "Dreams," the final story in Young Men, a mix of the real and the surreal involving a boyfriend who steals his girlfriend's thoughts when she's asleep. But as Jeet Heer, writing in Canadian Notes & Queries put it, "Since so much of Smith's art derives its power and trustworthiness from its firm grounding in the experiential world, this venture into semi-fantasy doesn't work."

Whiskheads is more successful than "Dreams" because he isn't caught halfway between Evelyn Waugh and Mother Goose. The story is short, light, rapid and full of vivid scenes: "Soon she was in the city proper, in the narrow residential streets where every window bore a flower box full of bright petals and the walls rustled with vines." Wesley W. Bates' many illustrations are excellent and resonate with the text. And as long as the reader doesn't pause to reflect, no major flaws emerge.

But a closer look revels that most everything Smith excels at is frustrated by the Once Upon a Time franchise. Dialogue is direct where normally it's nuanced. The lack of character development is bothersome -- Juliana is barely introduced before she hacks off her long hair and runs off to snoop on the Whiskheads. Much of the wit, grace and subtly of Smith's first three books seem to have disappeared somewhere enroute to this new, magical, mystical kingdom.

Smith mocked cobweb Canlit in Noise with something called the Responsible Fiction Award. It was the perfect description of ponderous, good-for-you, oatmeal prose that Canadians often praise yet rarely read. But when the Princess declares Stjornokh a Banality Free Zone, the earnestness is cringe-worthy; hardly in keeping with Smith's sardonic persona.

Sheila Heti successfully tweaked the fairy tale format with last year's The Middle Stories. There was something fun about reading about young moderns ("Oh God, I slept with a vegan.") described with sing-song prose. Smith reverses the formula, but Queen Street West transplanted into cobblestone streets and castles isn't as successful. Smith doesn't comment on his cultural anachronisms, even slyly. Unlike Heti, Smith isn't able to bend the formula to suit his strengths, to shape the genre into something uniquely his.

Not that Whiskheads is too steeped in the traditional. Certainly, the princess has difficulty staying clothed, and she sleeps with Jan, the Whiskhead leader (an action verboten in "real or traditional" fables) on their second date. But carnality aside, this Secret World of Id has much more in common with the Secret World of Og.

Smith normally observes and documents his urban surroundings. This time, he has had to create and populate a unique universe. Smith should be commended for taking risks, but experiments often are exactly that. Those who enjoy his writing will be disappointed. It's a diversion, with all the positives and negatives such a word connotes.

Smith, in trying to escape the tyranny of style over substance and the eternal present his characters normally inhabit, has looked to the past, but satisfies no one in the process. Philosopher Gilbert Ryle called this kind of mismatch a category mistake. Smith should avoid making such an error again, if he wants his writing career to have a happy ending.