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!

"It's good to know who you are, and Kennedy does (check the title); he'll have you laughing, simply glad you aren't him. A little gem, but it's excruciating to imagine paying the price for the material." Kirkus Reviews

"Part mock Chicken Soup for the Slacker...and part Sedaris-style essay collection, this episodic book presents Kennedy from his normal-but-awkward childhood to his normal-but-still-awkward adulthood." Publishers Weekly

"We cringe delightedly as Kennedy records his inability to make small talk, smart decisions, or much of himself. And when he does finally deliver his insights, it's not with a self-aggrandizing shout but a welcome, modest shrug." Keir Graff, Booklist

From tearing up the pages of McSweeney's and Bookforum to his first "self un-help" book, Kennedy presents a memoir of the spectacular failures, hilarious humiliations, and dumb choices that have dogged his 33 years.

Jerry Stahl calls him "the hipster Proust of youthful loserdom." He's torn up the stages of New York's literary scene and the pages of McSweeney's with his funny, scathingly self-crucifying prose. Now, Dan Kennedy presents a memoir of the spectacular failures, hilarious humiliations, and just plain silly choices that have dogged his first 33 years. Fans of confessional, tongue-in-cheek 30-somethings like David Sedaris, Sandra Tsing Loh, and Nick Hornby, as well as fans of Dan Kennedy's popular McSweeney's pieces, will fall over laughing.

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!

DAN KENNEDY is a contributor to McSweeney’s and Bookforum and performs regularly at Stories at The Moth as well as other gigs around town. He lives in New York and is Director of Creative Development for Atlantic Records.