Reviewer: SteveJ
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Waiting to Derail:
Ryan Adams and Whiskeytown, Alt-Country's Brilliant Wreck
280 pages
June 26, 2018
ISBN 10:
ISBN 13:

Provides a firsthand glimpse into Ryan Adams at the most meaningful and mythical stage of his career.

There are several schools of thought you hear about Ryan Adams. One is that he is the most gifted and talented songwriter of his generation. The other is that Adams is a train wreck, a waste case that continually sabotages his own career through reckless and juvenile behavior. And, of course, there is the theory that Adams is all of the above, and that is the one advanced by Thomas O’Keefe in his new book Waiting To Derail: Ryan Adams and Whiskeytown, Alt-Country’s Brilliant Wreck.

After quitting the punk rock band ANTiSEEN and moving to North Carolina, O’Keefe served as as Whiskeytown’s tour manager from 1997 — when Adams was all of 22— to 2000, when Ryan would call it quits to go solo. O’Keefe would experience many highs, likely a great many more lows, and one hell of a ride. “Ninety percent of the time, I could talk Ryan into doing the right thing. Five percent of the time, I could cover up whatever idiotic thing Ryan had done. But that final five percent? We were fucked.”

It’s important to note the timeframe this story takes place in; so-called “alt-country” —a  phrase Adams hated — wasn’t yet close to becoming mainstream. As O’Keefe notes early on: “It had a lot of buzz, but still hadn’t made much of a dent in the marketplace."  O’Keefe also drops many more monikers for the genre such as twangcore, insurgent country and, my favorite, y’alternative, Still, Whiskeytown were the anticipated stars; Rolling Stone’s review of Strangers Almanac read, in part “If there’s to be a Nirvana” (in the alt-country world)…look to Whiskeytown.”

O’Keefe’s punk background plays pretty big in his outlook; in fact, he believes Ryan is actually a punk rocker at heart, and thus his bad behavior. It’s safe to say if Whiskeytown was booked into a sports bar, with the TV tuned to a game, the evening would not end well, with O’Keefe and crew racing to simultaneously get paid whatever he could, pack up the gear, and get the band out of harm’s way.

O’Keefe also dissects the band thusly, and I couldn’t agree more (parenthetical info is mine):
Ryan + Caitlan (Cary - fiddle and vocals) = The Musical Beauty of Whiskeytown
Ryan + Phil (Wandscher - guitar, songwriting, vocals and enabler) = The Punk Rock Spirit of Whiskeytown

A couiple of great records, brilliant gigs, and cancelled shows bear this out. Caitlan’s playing and especially her harmonies give the music a country legitimacy. Phil is described by the author as “Ryan’s fist-fighting, guitar-slinging brother” and “a key contributor to all the aforementioned dicking around.” That, in a nutshell, is the Whiskeytown dichotomy; ironically, both members would leave by the story’s end, with Phil being fired and Caitlan moving on.

Another talking point you often hear is addressed by O’Keefe: authenticity. Because of much of the above, there was always the viewpoint that Adams was just riding the surge of popularity of alt-country, the "so-called" next big thing.You rarely heard that criticism of Uncle Tupelo, for instance. Perhaps it started with the “accessibility” of Strangers Almanac but it dogged Ryan. Many journalists took Adams at his word when he sang “So I started this damn country band / Cause punk rock was too hard to sing.” The Boston Phoenix would ask “Does an artist who sings about hard times and unemployment have had to grown up in a tarpaper shack in Mississippi in order to be authentic? “Hell, no” answers O’Keefe — and there’s a long line of music legends to back that up.

I came to Whiskeytown late, via Adams solo records Heartbreaker, and especially Gold, perhaps his most commercial rock album. I now love Strangers Almanac, and, while I applaud his musical curiosity, I’ve found his solo career maddeningly inconsistent. O’Keefe was confounded as well when, after writing a particularly exceptional batch of tunes, Adams stopped performing them after a couple of times because he had moved on to working out the new ones in his head, and it would seem to be another in a  series of self-inflicted career wounds. Adams would tell journalists "Because I have a devil-may-care attitude and won’t grit my teeth and kiss ass, people keep sayin ‘Man you’re throwing it all away.” O’Keefe’s take: “The songs meant everything to him; the career meant nothing. But he didn’t realize  — or didn’t care — that so many other people’s fortunes were connected to him. When he pissed down his leg, he splashed everyone else.”

O'Keefe has authored a fun, easy and engaging read if you’re a Ryan Adams fan or a fan of rock star behaviour and highjinks on the road. Thomas O’Keefe spun the Whiskeytown gig into tour managing Weezer, Sia and Third Eye Blind, and his very detailed account reads straight-up and honest. Ryan Adams, however, remains a fascinating yet frustrating enigma.


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