Loser Goes First: My Thirty-Something Years of Dumb Luck and Minor Humiliation

It all begins on Christmas morning, 1978. Dan Kennedy is ten years old and wants a black Gibson Les Paul guitar, the kind Peter Frampton plays. It will be his passport to the coolest (only) band in the neighborhood—Jokerz. He doesn’t get it. Instead, his parents present him with what they think he wants most, a real-estate loan calculator (called the Loan Arranger) and a maroon velour pullover shirt with a tan stripe across the chest. It is the first of what will become a lifetime of various-sized failures, misunderstandings, comical humiliations, and just plain silly choices that have dogged this “hipster Proust of youthful loserdom,” as author Jerry Stahl has so eloquently called Mr. Kennedy.
Dan’s hilarious and painfully awkward youth soon develops into a . . . uh . . . hilarious and painfully awkward adulthood. His first two choices for university are Yale (Lit or Drama) and Harvard (Business), so he reviews his high school transcripts and decides on Butte Community College in Oroville, California, where he studies for about four and a half weeks. We could go on here and describe in detail all of Dan’s good-natured stabs at ambition, but he, himself, sums it all up quite nicely: “If you’ve ever tried and failed miserably at being a rock star (no guitar/talent), a professional bass fisherman, an extra in the movie Sleepless in Seattle (guy drinking martini in bar while Tom Hanks makes a phone call), a Madison Avenue advertising executive, a clerk/towel person at a suburban health club (named Kangaroo Kourts), an espresso street-cart owner and operator (in the one neighborhood of that coffee-swilling town, Seattle, where, remarkably, no one really seems to drink coffee), a dot.com millionaire, an MTV VJ, or a forest fire fighter, this book is for you.”
Along the way, a few lessons are learned and we are treated to one of the most original, riotously funny, unsentimental, and offbeat memoirs in recent history. Dan’s a favorite in McSweeney’s and at the very popular Moth readings in New York City. We should be happy that he failed so miserably at so many things—and took notes!

Many people spend their lives searching for their true calling, the one thing at which they excel and which will catapult them to fame and fortune. For Dan Kennedy, author of the darkly comic memoir Loser Goes First, that talent is decidedly not rock and roll. Kennedy details a life spent pining for the glory of rock stardom as a junior high student, an Austin, Texas, open-mic failure, and at various grim stops along the way as he shoots for the big time without the burden of talent or the tedium of learning to play an instrument. Kennedy's talent is also not acting, although he lands a gig as an extra in Sleepless in Seattle that leads, much to his chagrin, to nothing at all. Even his scrupulously cultivated talent of being an indie scenester is torpedoed when he willingly accepts an audition to be an MTV VJ, only to have the tryout be an unmitigated disaster. Finally, Kennedy discovers a pair of latent abilities. He finds, after he's into his thirties, that he has a knack for advertising copywriting that sets him on the path to his first financial success almost accidentally. And in writing Loser Goes First, he reveals a talent for relating his own dumb moves and embarrassing fiascoes with an honesty and wit that is vividly entertaining. Loser Goes First approaches narrative structure with the same indecisive distracted quality that Kennedy used in his actual life and the result is a chronicle of Kennedy's first 33 years peppered generously with film treatments, bullet point lists, imagined dialogue, and other snippets that seem transcribed from a very clever notebook. While such meandering could be perceived as too self-consciously quirky, it matches the story and keeps the humor crisp. --John Moe

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