Waiting to Derail

Waiting to DerailREVISEDCOVER
The definitive account of the Americana legends—told by the man who tried to keep the train on the tracks.

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.

For the next 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.


“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

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

“This is perhaps the most significant book about the heralded Triangle music scene of the mid 90s, one that could have only been written by someone who was there to experience it every step of the way. It was a time when every music exec was keeping an eye (and ear) on the region, waiting for the prediction that it would be the next Seattle to come true, and no musical act created more buzz than Whiskeytown. Full of stories from the period and details that will surprise even the biggest Ryan Adams fan. O’Keefe has given us a document that will be studied for years to come by music historians and fans in general, with both asking the same question from different angles: “What happened?”

―Isaac Weeks, Contributor, Billboard Magazine and The Raleigh News & Observer

“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


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