Waiting to Derail
Ryan Adams and Whiskeytown, Alt-Country's Brilliant Wreck
Will be published approx. on 29. January 2026
Book
Paperback/Softback
280 pages
978-1-5107-8641-7 (ISBN)
Description
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.
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.
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.
Reviews / Votes
"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 a hard book to put down-especially if you love Ryan Adams. Thomas O'Keefe takes the reader inside the van and the venues to give us an entertaining collection of stories from Ryan's days in Whiskeytown."
-Alex LeCavalier, Third Eye Blind
"For those of us who were there-attended the shitshows, bought the records, dutifully wrote it all up for No Depression, can actually recall Y'alternative's moment in the sun-Thomas O'Keefe's book is more than just a ringside seat to the haymakers being wildly thrown. Waiting to Derail is an important analysis of the promise and the pratfalls of Ryan Adams before he was Capital R, Capital A Ryan-a snotty-nosed punk with talent to burn and a once-in-a-generation songwriting gift. If anything, the book tells us as much about the times, and the author, as it does Adams himself. The most solid gold rock read of 2018 to date. "
-Corey duBrowa, VP Global Communications and Public Affairs at Google, freelance writer
"I loved this book! I've known author Thomas O'Keefe since the day Train opened for Whiskeytown in 1998. I've always been a big Ryan Adams fan (Stranger's Almanac is still one of my all-time favorite albums) so I used to love when Thomas would share his Whiskeytown stories with us on the bus while he was Train's tour manager. And now he's sharing them with you. This book is an up close and personal, behind the scenes glimpse into the life of a young genius trying to find his way."
-Jimmy Stafford , guitarist, Train "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
"Waiting To Derail is an anomaly among rock bios. Written with a remarkable and refreshing approach, O'Keefe captures the atmosphere honestly while maintaining a respect and affection for his subject. Here is the raw, candid truth of an emerging talent struggling to confront his inevitable stardom told from a firsthand perspective without bitterness or sleazy cynicism."
-Russ Ward , ANTiSEEN
"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
"You know how every kid wants to run away with the circus? It seems some of them actually did, except their circus was disguised as a rock band. Waiting to Derail makes me want to light a cigarette, crack open a beer, and get on a tour bus again."
-Van Alston, Legendary Raleigh Bar Owner and former Ryan Adams tour manager
"Waiting to Derail is a two-sided story that deals with the conflict between a brilliant songwriter who's talent eclipses his years and his defiant, punk ethos that threatens to destroy all of the progress and potential that those who believe in him are trying to help him realize. "
-Jeremy Porter, Pencilstorm
"The book was like finding a long lost book of photographs. I totally got lost in it."-Greg Miller, Nurse the Hate
"Waiting to Derail is a book that is wholly original, frenetic, and nearly impossible to put down."
-Greg Robson
"If anybody's likely to have the inside scoop on the ups and downs that Ryan Adams, Caitlin Cary, and the rest of the troupe experienced while they were out there blazing a trail for hordes of Americana acts to follow, it's O'Keefe. Coming on board right around the time of Strangers Almanac's release and helping the band fulfill its destiny, at least for a while, the author had a front row seat for the heaviest part of Whiskeytown's history, and he isn't shy about sharing it."-Jim Allen, IndyWeek
"O'Keefe does not disappoint. His memory is remarkably clear, his insights into Adams' personality and motivations profound. Waiting To Derail is the type of book that any fan of rock 'n' roll-and of course all fans of Adams- will devour precisely for its fly-on-the-wall qualities and how it provides a sharp-lensed view of what goes on after the lights come on and the gear is packed up."-Fred Mills, Blurt
"I was lucky enough to play shows with Whiskeytown and witnessed many ups and downs. This story shows the true test of friendship of these two punk rock guys navigating the major label world of rock and roll."-Tim Buckley, Maki
"I didn't want it to be over... READ THIS BOOK!"-Daily Vinyl
"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."-Issac Week, News & Observer, Raleigh, NC "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 a hard book to put down-especially if you love Ryan Adams. Thomas O'Keefe takes the reader inside the van and the venues to give us an entertaining collection of stories from Ryan's days in Whiskeytown."
-Alex LeCavalier, Third Eye Blind
"For those of us who were there-attended the shitshows, bought the records, dutifully wrote it all up for No Depression, can actually recall Y'alternative's moment in the sun-Thomas O'Keefe's book is more than just a ringside seat to the haymakers being wildly thrown. Waiting to Derail is an important analysis of the promise and the pratfalls of Ryan Adams before he was Capital R, Capital A Ryan-a snotty-nosed punk with talent to burn and a once-in-a-generation songwriting gift. If anything, the book tells us as much about the times, and the author, as it does Adams himself. The most solid gold rock read of 2018 to date. "
-Corey duBrowa, VP Global Communications and Public Affairs at Google, freelance writer
"I loved this book! I've known author Thomas O'Keefe since the day Train opened for Whiskeytown in 1998. I've always been a big Ryan Adams fan (Stranger's Almanac is still one of my all-time favorite albums) so I used to love when Thomas would share his Whiskeytown stories with us on the bus while he was Train's tour manager. And now he's sharing them with you. This book is an up close and personal, behind the scenes glimpse into the life of a young genius trying to find his way."
-Jimmy Stafford , guitarist, Train "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
"Waiting To Derail is an anomaly among rock bios. Written with a remarkable and refreshing approach, O'Keefe captures the atmosphere honestly while maintaining a respect and affection for his subject. Here is the raw, candid truth of an emerging talent struggling to confront his inevitable stardom told from a firsthand perspective without bitterness or sleazy cynicism."
-Russ Ward , ANTiSEEN
"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
"You know how every kid wants to run away with the circus? It seems some of them actually did, except their circus was disguised as a rock band. Waiting to Derail makes me want to light a cigarette, crack open a beer, and get on a tour bus again."
-Van Alston, Legendary Raleigh Bar Owner and former Ryan Adams tour manager
"Waiting to Derail is a two-sided story that deals with the conflict between a brilliant songwriter who's talent eclipses his years and his defiant, punk ethos that threatens to destroy all of the progress and potential that those who believe in him are trying to help him realize. "
-Jeremy Porter, Pencilstorm
"The book was like finding a long lost book of photographs. I totally got lost in it."-Greg Miller, Nurse the Hate
"Waiting to Derail is a book that is wholly original, frenetic, and nearly impossible to put down."
-Greg Robson
"If anybody's likely to have the inside scoop on the ups and downs that Ryan Adams, Caitlin Cary, and the rest of the troupe experienced while they were out there blazing a trail for hordes of Americana acts to follow, it's O'Keefe. Coming on board right around the time of Strangers Almanac's release and helping the band fulfill its destiny, at least for a while, the author had a front row seat for the heaviest part of Whiskeytown's history, and he isn't shy about sharing it."-Jim Allen, IndyWeek
"O'Keefe does not disappoint. His memory is remarkably clear, his insights into Adams' personality and motivations profound. Waiting To Derail is the type of book that any fan of rock 'n' roll-and of course all fans of Adams- will devour precisely for its fly-on-the-wall qualities and how it provides a sharp-lensed view of what goes on after the lights come on and the gear is packed up."-Fred Mills, Blurt
"I was lucky enough to play shows with Whiskeytown and witnessed many ups and downs. This story shows the true test of friendship of these two punk rock guys navigating the major label world of rock and roll."-Tim Buckley, Maki
"I didn't want it to be over... READ THIS BOOK!"-Daily Vinyl
More details
Edition
Reissue
Language
English
Place of publication
New York, NY
United States
Product notice
Paperback (trade)
Illustrations
16 p b-w insert
Dimensions
Height: 229 mm
Width: 153 mm
Thickness: 15 mm
Weight
265 gr
ISBN-13
978-1-5107-8641-7 (9781510786417)
Copyright in bibliographic data and cover images is held by Nielsen Book Services Limited or by the publishers or by their respective licensors: all rights reserved.
Schweitzer Classification
Persons
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 in Esquire, 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.
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 in Esquire, 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.