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Waiting to Derail: Ryan Adams and Whiskeytown

Alt-Country’s Brilliant Wreck By Thomas O’Keefe with Joe Oestreich

The definitive account of the Americana legends--told by the man who tried to keep the train on the tracks

On Sale: June 26, 2018

“A well-written tale of Whiskeytown, one of my all-time favorite bands. In Waiting to Derail, O’Keefe brings the ’90s alt-country scene to life. What a great read!”

―Bun E. Carlos, Cheap Trick


Long before the Grammy nominations, sold-out performances at Carnegie Hall, and Hollywood friends and lovers, Ryan Adams fronted a Raleigh, North Carolina, outfit called Whiskeytown. Lumped into the burgeoning alt-country movement, the band soon landed a major label deal and recorded an instant classic: Strangers Almanac. That's when tour manager Thomas O'Keefe met the young musician.


O’Keefe, with Joe Oestreich, recounts the wild and dramatic ride he took with Whiskeytown in Waiting to Derail: Ryan Adams and Whiskeytown, Alt-Country’s Brilliant Wreck (Skyhorse Publishing, June 26, 2018) For three years, Thomas was at Ryan's side: on the tour bus, in the hotels, backstage at the venues. Whiskeytown built a reputation for being, as the Detroit Free Press put it, "half band, half soap opera," and Thomas discovered that young Ryan was equal parts songwriting prodigy and drunken buffoon. Ninety percent of the time, Thomas could talk Ryan into doing the right thing. Five percent of the time, he could cover up whatever idiotic thing Ryan had done. But the final five percent? Whiskeytown was screwed.


Twenty-plus years later, accounts of Ryan's legendary antics are still passed around in music circles. But only three people on the planet witnessed every Whiskeytown show from the release of Strangers Almanac to the band's eventual breakup: Ryan, fiddle player Caitlin Cary, and Thomas O'Keefe. And of the three of them, Thomas is the only one who was sober enough to remember it all. Packed with behind-the-scenes road stories, and, yes, tales of rock star debauchery, Waiting to Derail provides a firsthand glimpse into Ryan Adams at the most meaningful and mythical stage of his career.


About the Authors:

Thomas O'Keefe was the tour manager for Ryan Adams and Whiskeytown from 1997 until their breakup in 2000; he is currently the tour manager for Weezer. His twenty-plus year career in the music business includes twelve years with Grammy winners Train and shorter stints with acts as diverse as D Generation, Sia, Third Eye Blind, and Mandy Moore. He was also the bass player for North Carolina punk band ANTiSEEN, recording thirty-eight releases and playing concerts across the United States and Europe. O'Keefe lives in Nashville, Tennessee.


Joe Oestreich is the author of three books of creative nonfiction: Partisans, Lines of Scrimmage (cowritten with Scott Pleasant), and Hitless Wonder. His work has appeared inEsquire, Creative Nonfiction, River Teeth, Fourth Genre, The Normal School, and many other magazines and journals. Four of his pieces have been cited as notable essays in the Best American series, and he's received special mention twice in the Pushcart Prize anthology. He teaches creative writing at Coastal Carolina University. Oestreich lives in Myrtle Beach, South Carolina.


Waiting to Derail

Ryan Adams and Whiskeytown, Alt-Country’s Brilliant Wreck

By Thomas O’Keefe with Joe Oestreich

Skyhorse Publishing hardcover, also available as an ebook

On Sale: June 26, 2018 | ISBN: 978-1510724938 | Price: $21.99


Praise for Waiting to Derail

“Waiting to Derail is so legit you can almost smell the aroma of tour bus and stale beer rising from the pages. If you want to understand how rock and roll is simultaneously one of the coolest and most insane things on the planet to devote your life to, then you need to read this book.” —Lou Brutus, syndicated radio host


“In my years as a rock and roll barfly-on-the-wall I’ve heard my share of great stories. I’ve said ‘you oughta write a book’ more than a few times. I’m sure I said it to Thomas O’Keefe one night a long time ago because his Ryan Adams and Whiskeytown tales are pure gold. He and Ryan both survived, and he brought this document back from the front lines. You oughta read this book.”—Brian Phillips, morning disc jockey, WWCD


“I’ve been making rock and roll road stories with Thomas O’Keefe all over the globe since the early ’80s. Thomas has such a vivid, clear memory of what happened (and didn’t) that to this day I still consult with him as ‘fact checker.’ No one can tell those tales as well as he can.” —Jeff Clayton, ANTiSEEN