"Loser Goes First" by Dan Kennedy

But the moment Kennedy pinpoints the benefits of any one career or hobby, he's already moved on to something else. After describing the excitement of fighting real fires, he quickly admits that, instead of getting into it and maybe even looking forward to the next fire season, "All I was thinking was, A hundred dollars a day before taxes? This is a rip-off. I should try something else. Maybe be a songwriter or something."

Kennedy's honesty is admirable, and it makes him a humble but sure-footed storyteller. His description of performing at an open-mike night in Austin, Texas, is unforgettable. Armed with bad guitar skills, a bunch of distortion pedals and a notebook of rambling suggestions for possible lyrics, Kennedy tanks dramatically, in front of an audience of musicians, their mandolins and violins in tow. More than being disgusted or annoyed, the crowd looks at him "as if I'm their little brother or their son and it's just kind of cute that I even got up there and tried."

After relocating to Seattle -- just in time to miss the bad-guitar-and-distortion explosion there -- Kennedy is brutally honest about his reasons for wanting to become a counterperson at an espresso cafe. He imagines that such types are generally "sort of leftist, vaguely well-traveled underachievers with a neo-hippie influence and a solid catalog of '70s pop culture references ... This job would make me cooler and no longer quite the misfit. Instead I would seem like a misfit by choice, plus somehow smarter than you about government and art and things like that."

An undeniably entertaining writer, Kennedy offers a backstage tour of every pose and clumsy maneuver in his history, and combines a flair for creative adjectives, a litany of pop-culture references and amusing digressions to make the frustrations and absurd twists of his experience feel utterly palpable. Once you get used to the meandering pace of his prose, his vivid descriptions nicely capture those intense moments of powerlessness when your oppressors become larger than life. His boss at the espresso cafe, for one, was prone to springing surprise tests on his employee. Kennedy reports that it was easy to tell when such a test was coming because his boss would "wear that pressurized little grin that is supposed to convey good cheer, but when mixed with his trademark stress and almost amphetamine congeniality, looks more like a sitcom version of Jack Nicholson in 'The Shining.' It looks like the grin of a confused jackal or a pestered coyote, or of an uncle resentfully attending a family cookout that took him away from a horse race or a hooker, but since nobody in the family really knows about horse races or hookers, he just sits there with the consolation prize of Coors beer and hamburgers, acting happy to see you ... that kind of grin." Ah, yes. We know that grin.

Like any humorist, Kennedy exaggerates, and at times his actions and ideas are so unbelievably dense, it's tough to accept that such a sharp writer could have been quite so confused. His dimwit tone works fairly well on the whole, though, and the odd lists and strange jokes scattered throughout the book are a lot of fun. This from "A Few of the Lies I've Told You as an Advertising Copywriter": "Your children would rather have other parents based solely on the fact that you aren't serving meals that are as fun as the meals being served by your neighbors, but if you purchased these frozen meals, your family would be somehow better and more fun, like the neighbors whom your kids love more than you."

Sometimes Kennedy fancies himself as awfully cute. Sometimes he wanders into roundabout jokes that are hard to follow and not all that amusing. But considering the hipster drivel you might expect from a book with the subtitle "My Thirty-Something Years of Dumb Luck and Minor Humiliation" -- a book you might be likely to loathe, sight unseen, out of sheer boredom with the self-flogging, snarky voice of the moment -- "Loser Goes First" is irresistibly weird and brave and satisfying. Most of all, though, it will make you damn glad that you're no longer forced to fold mock turtlenecks and confront felons, while listening to the soul-crushing strains of "Papa Was a Rolling Stone" one more time.

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