Loser Goes First

Dan Kennedy is a very funny man. And like most funny people, he has a lot of balls. Because – and this is something that most unfunny people don’t realize – it takes real cojones to be funny. Comedy is about surprise and constantly stepping off the edge of the cliff with only your innate sense of timing and structure to save you. And that takes courage.

But it takes a particular brand of that courage to write a memoir when you’re only in your thirties. Because for most people, it isn’t until at least our thirties that we have anything worth saying. Up to that point we’ve spent most of our time going down blind alleys, exploring dead ends, and doing the kinds of things that years later, we’ll look back and say “what the hell was I thinking?”

If we’re lucky, by the time we get to our thirties, things have turned some sort of corner. What was once clumsy and awkward and unexplainable has become celebrated and honored and respected. There’s a lot of hardware and a lot of “oh, so that’s what he was talking about…”

But write a memoir in your thirties and you’re just advertising the fucking up. The dead-end jobs, your own overinflated estimations of your worth, the dreams of being picked out of the crowd at a rock concert by a legendary band to save the show (Scot Halpin notwithstanding). It’s like Michael Jordan writing a memoir right after he got cut from his high school basketball team.

But this is sort of Dan Kennedy’s bread and butter. Anyone who’s read his hysterically funny pieces in McSweeney’s or seen him tell stories at The Moth, or has read his essays in GQ, knows that public embarrassment, social awkwardness, bad decisions, misguided pursuits and some form of private humiliation are just a few of the many colors that form his palette, from which he paints elaborately funny stories that will have you shooting beverages out of your nose and giggling embarrassedly on the subway. Hopefully not at the same time.

And nowhere are these skills more on display than in Loser Goes First: My Thirty-Something Years of Dumb Luck and Minor Humiliation, Kennedy’s self-effacing – one might even say, self-defacing – memoir of his trials and dreams of tribulations.

Beginning with his childhood in Northern California, Kennedy weaves a tapestry that will be instantly recognizable to the thousands of creatives who toil in agencies – a fate Kennedy himself has experienced and writes about in the chapter “New, Improved and Easier to Use: My Short Ride on Madison Avenue”. One that begins with his dreams as an 11-year-old about a guitar for Christmas that will enable him to join the coolest (and only) band in school (in spite of the fact that he doesn’t know how to play). That evolves to his post-high school years when he decides to move to the next big music city (Seattle or Austin? Oh, and he still can’t play guitar). And then the decision that gets him to New York City – his audition with MTV to be a VJ (remember those? Nina Blackwood. Alan Hunter. The black guy. Spoiler alert, it doesn’t work out).

This litany of mistakes might be depressing if it weren’t for three things. First, this is how we learn. We make mistakes. And in some respects, that’s what youth is for. Sure, sure, if someone tells you “fire hot”, you can save yourself a burned-off hand by listening to him. But that aside, youth is when you’re supposed to go down blind alleys and find out they’re blind alleys. Better to do it when you’re young than when you’re too old to find your way out again.

And second, this is how we learn. Sure, the specifics of Dan’s details are different from yours, and yours are different from mine, and mine are different from the poor slob sitting in the cubicle next to you trying to make sense of the client’s changes. But the broad strokes are the same. There’s no template, no direct path, no right way to do this. In fact, the case could even be made that an indirect path is the best path to this business – it encourages those who are curious and dissuades those who aren’t.

And the third reason it’s not depressing? Because Dan Kennedy is a very funny man. Now if you’ll excuse me, I have to clean up some beverage that’s been shooting out of my nose…

Loser Goes First: My Thirty-Something Years of Dumb Luck and Minor Humiliation by Dan Kennedy was published by Crown on 09/16/03 – order it from Amazon here or from Barnes & Noble here – or pick it up at your local bookseller ( find one here).