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Waiting to Derail: Ryan Adams and Whiskeytown, Alt-Country's Brilliant Wreck
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 Strangers Almanac. That's when tour manager Thomas O'Keefe met the young musician. For the next three years, Thomas was at Ryan's 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 Ryan, fiddle player Caitlin Cary, and Thomas O'Keefe. 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.
266 pages, Kindle Edition
Published June 26, 2018
26 people are currently reading
149 people want to read
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Displaying 1 - 30 of 35 reviews
December 31, 2018
Full of those industry-speak paragraphs that are so prevalent in mid-80s to 00s industry voices. "they were an outfit from _____________ who coulda been huge man!" The internet age gets a lot of shit for killing off the album and the record labels....but I think we forget how insufferable those times were.
that said. O'Keefe was in the shit with one of the great American bands of the 90s, Whiskeytown. And so it's worth the price just to roll your eyes now and again.
that said. O'Keefe was in the shit with one of the great American bands of the 90s, Whiskeytown. And so it's worth the price just to roll your eyes now and again.
June 26, 2018
When Ryan Adams was fronting the alt-country band Whiskeytown, they were notorious for being unpredictable, unreliable, sometimes brilliant, but many times just chaotic and drunk. Brilliant song-writing talent was offset by childish and ridiculous behavior. Thomas O'Keefe was the tour manager hired by their record company for the tour to promote their breakthrough major label album, Strangers Almanac. This book is the story of that legendary and chaotic tour and the subsequent implosion of the band told from an insider's point of view. An important and exasperating part of alt-country history. - BH.
February 4, 2025
3.5 stars. I was a big fan of Whiskeytown and Ryan Adams until Ryan was accused of sexually harassing several women. I still listen to his old music, I just haven’t bought any of his new stuff that’s come out since the allegations surfaced.
This book makes Ryan sound like a very talented but temperamental asshole. It was fun to read about his exploits though.
This book makes Ryan sound like a very talented but temperamental asshole. It was fun to read about his exploits though.
July 19, 2018
Insightful. A good look at the early days of Mr. Adams told from the perspective of someone who saw it all. Told in great detail, this story of 90's nostalgia will make you laugh and cringe at the same time.
A great look at how bands go from the top to the bottom.
A great look at how bands go from the top to the bottom.
Want to read
June 27, 2018I can tell from the cover alone that this is going to be awful, but I'm such an unabashed DRA fan I'll indulge it nonetheless eventually, right after I read the Menconi book.
July 12, 2018
I read this because I love Ryan Adams. Unfortunately, this book fell short of providing any real insight into Adams other than repetitively describing him as a wreck or a genius. The book is a very linear tour diary describing Adam's antics on a daily basis. The book clearly suffers due to the lack of involvement from Adams and thus can only provide a snapshot of anecdotes from O'Keefe's time as a manager.
I think the book O'Keefe wanted to write may have been more successful - a memoir of the industry and time as a tour manager, contrasting different artists and tour experiences over time. There were too many details about the author, his wife, band, etc., that felt unnaturally placed here in a "bio" of Adams.
The book was enjoyable and a fast read, but didn't tell me much I didn't already know.
I think the book O'Keefe wanted to write may have been more successful - a memoir of the industry and time as a tour manager, contrasting different artists and tour experiences over time. There were too many details about the author, his wife, band, etc., that felt unnaturally placed here in a "bio" of Adams.
The book was enjoyable and a fast read, but didn't tell me much I didn't already know.
October 18, 2018
Waiting to Derail was a pretty durn interesting read. I didn't really know what to expect going in, as I knew absolutely nothing about Ryan Adams beforehand. I got nervous for a second; the book flap and Intro let me know that this was an unauthorized bio. Sometimes those get almost vindictive of the subject. But this one was really good and objective. The author was Ryan Adam's first tour agent, so he spent a lot a lot of time with him. Ryan even lived in his house with him and his girlfriend in between tours sometimes. The author never seems like he's being mean in recounting any stories, even when they don't paint Ryan in the best light. He's just stating facts. And he makes sure to spend a much larger amount of time recounting stories that show the depth and breadth of Ryan's talent and drive.
I would definitely recommend for Whiskey Town and/or Ryan Adams fans!
I would definitely recommend for Whiskey Town and/or Ryan Adams fans!
July 29, 2018
Meh. Definitely not a "tell-all," this book is more of a "tell enough to get the book published but not enough to burn bridges if I can work with them again someday." Not enough real detail to provide any insight, the overall lesson is that one of the greatest songwriters of all time was kind of a douche to the actual human beings he interacted with on a daily basis, but he could also be really fun to hang out with when he was in a good mood. But if you follow Ryan Adams enough to read this book, you already know that.
July 20, 2022
Thomas O'Keefe is a North Carolina punk rocker who spent over a decade playing in bands and touring across the USA and Europe after graduating high school, notably as a member of ANTiSEEN from 1988 through 1995. During the latter part of his time in ANTiSEEN O'Keefe assumed some important business-end responsibilities for the group and even served as its manager for a brief period. This turned out to be valuable experience in the next phase of his career, as he began working as a tour manager for Lustre in 1996. Then in 1997 he received a call to serve as tour manager for an up-and-coming alt-country band out of North Carolina called Whiskeytown, fronted by a volatile 22-year-old songwriter named Ryan Adams. That job, which consumed the next few years of O'Keefe's life, is the subject of Waiting to Derail.
Thanks to a detailed expose published in the New York Times in February 2019, Adams came under harsh scrutiny for his behavior toward an array of women, with allegations that he "dangled career opportunities while simultaneously pursuing female artists for sex." But long before publication of the Times piece, which did impede his career for the next several years, Adams' personal reputation was hardly stellar. Among music fans and others, Adams was already well-known for his unprofessional behavior, which included numerous on-stage tantrums, hurling abuse at fans and critics, appearing at gigs drunk or drugged (or both), indulging in violent rages, badmouthing other musicians, and generally carrying on like a narcissistic spoiled child. Yet Adams also has genuine talent as a songwriter and musician and he's released numerous high-quality songs throughout a career that has spanned almost 30 years.
These two aspects of Adams' persona - the genuine talent and the appallingly bad behavior - are the chief focus of O'Keefe's chronicle of his stormy years as Whiskeytown's tour manager. Hired in the spring of 1997 to get the band through a nationwide tour in support of its first major-label album, Strangers Almanac, O'Keefe found his punk rocker past earned him a large degree of respect and credibility from Adams, and O'Keefe in turn was soon convinced of Adams' songwriting chops as well as an ability to put his songs across to an audience with no more than an acoustic guitar. It was Adams' bad habits, however, that dominated the tour from start to finish, and O'Keefe's account is by turns harrowing and morbidly hilarious. Adams' propensity for self-sabotage was in full throttle during Whiskeytown's tours of 1997 and 1998. Among other things, Adams frequently overslept; missed calls to get on the road in time to reach the next stop on the tour; engaged in childish fights with bandmate Phil Wandscher for hours on the road; drank and drugged himself to excess before a show with predictable results for the performance; antagonized audiences and venues by abruptly ending gigs, playing too-short sets, canceling gigs, launching into noisy feedback, and damaging house equipment; refusing to cooperate with standard promotional tasks like radio interviews and performances; and many other shenanigans.
Then, with four shows left on the initial leg of their 1997 tour Adams announced from the stage in Kansas City that Whiskeytown was finished and summarily fired everyone in the band except violinist and vocalist Caitlin Cary. It took lots of convincing on the part of O'Keefe and others to get Adams to agree to resume the next leg of the tour with a new set of musicians, but this had little impact on his behavior and the band eventually fell apart as Adams lost interest in sustaining it, preferring to embark on the solo career he has pursued ever since.
O'Keefe's narrative is well-paced, reasonably engaging, and strangely neutral given how much stress and unpleasantness he must have endured trying to get Whiskeytown through two years of touring while the band exploded and imploded. In this he probably shared a willingness with the rest of the band to put up with a lot, betting on the chance that Adams' talent could catapult Whiskeytown to lucrative commercial success - but it was not to be. As O'Keefe notes in the Epilogue, he collected insights by speaking with all the principal participants in the events he recounts except for Ryan Adams, who (unsurprisingly) declined to be involved. Since his baptism by fire, O'Keefe has gone on to a long career in tour and artist management with other musicians who gave him far less trouble. He probably doesn't miss dealing with Adams all that much.
Thanks to a detailed expose published in the New York Times in February 2019, Adams came under harsh scrutiny for his behavior toward an array of women, with allegations that he "dangled career opportunities while simultaneously pursuing female artists for sex." But long before publication of the Times piece, which did impede his career for the next several years, Adams' personal reputation was hardly stellar. Among music fans and others, Adams was already well-known for his unprofessional behavior, which included numerous on-stage tantrums, hurling abuse at fans and critics, appearing at gigs drunk or drugged (or both), indulging in violent rages, badmouthing other musicians, and generally carrying on like a narcissistic spoiled child. Yet Adams also has genuine talent as a songwriter and musician and he's released numerous high-quality songs throughout a career that has spanned almost 30 years.
These two aspects of Adams' persona - the genuine talent and the appallingly bad behavior - are the chief focus of O'Keefe's chronicle of his stormy years as Whiskeytown's tour manager. Hired in the spring of 1997 to get the band through a nationwide tour in support of its first major-label album, Strangers Almanac, O'Keefe found his punk rocker past earned him a large degree of respect and credibility from Adams, and O'Keefe in turn was soon convinced of Adams' songwriting chops as well as an ability to put his songs across to an audience with no more than an acoustic guitar. It was Adams' bad habits, however, that dominated the tour from start to finish, and O'Keefe's account is by turns harrowing and morbidly hilarious. Adams' propensity for self-sabotage was in full throttle during Whiskeytown's tours of 1997 and 1998. Among other things, Adams frequently overslept; missed calls to get on the road in time to reach the next stop on the tour; engaged in childish fights with bandmate Phil Wandscher for hours on the road; drank and drugged himself to excess before a show with predictable results for the performance; antagonized audiences and venues by abruptly ending gigs, playing too-short sets, canceling gigs, launching into noisy feedback, and damaging house equipment; refusing to cooperate with standard promotional tasks like radio interviews and performances; and many other shenanigans.
Then, with four shows left on the initial leg of their 1997 tour Adams announced from the stage in Kansas City that Whiskeytown was finished and summarily fired everyone in the band except violinist and vocalist Caitlin Cary. It took lots of convincing on the part of O'Keefe and others to get Adams to agree to resume the next leg of the tour with a new set of musicians, but this had little impact on his behavior and the band eventually fell apart as Adams lost interest in sustaining it, preferring to embark on the solo career he has pursued ever since.
O'Keefe's narrative is well-paced, reasonably engaging, and strangely neutral given how much stress and unpleasantness he must have endured trying to get Whiskeytown through two years of touring while the band exploded and imploded. In this he probably shared a willingness with the rest of the band to put up with a lot, betting on the chance that Adams' talent could catapult Whiskeytown to lucrative commercial success - but it was not to be. As O'Keefe notes in the Epilogue, he collected insights by speaking with all the principal participants in the events he recounts except for Ryan Adams, who (unsurprisingly) declined to be involved. Since his baptism by fire, O'Keefe has gone on to a long career in tour and artist management with other musicians who gave him far less trouble. He probably doesn't miss dealing with Adams all that much.
December 29, 2018
Ryan Adams is one of my favorite artists. I first discovered him in Whiskeytown with 16 Days, which got a lot of radio play. But it wasn’t until i picked up a copy of Gold that i really got into Ryan Adams and that’s when i bought the Whiskeytown albums, Faithless Street, Strangers Almanac (awesome!) and Pneumonia. From there i bought his other solo albums, my favorite being Heartbreaker. I also love Cold Roses (Let it Ride is one of my favorite songs), Ashes and Fire, and i can’t even remember the rest of the titles. I have a lot of his music in my library. So i wanted to know more about the artist.
I read Losering earlier this year about Ryan Adams. I had read many articles about him too. He is a musical mercurial genius and a total brat. I had long heard about his antics at live concerts so i never had a desire to attend one, but i always anticipated his next record, and like his concerts, which were hit or miss, i passed on buying a few of them, Rock N Roll, the Taylor Swift 29 which i feel was meant as sheer mockery and him being an asshole, though i guess from some, it worked.
This book is written by his tour manager and is a first hand account of his dealing with Ryan. I don’t know how O’Keefe didn’t suffer some sort of heart attack trying to keep Ryan in line. I’m glad for him he got out. This book reads similar to Menconi’s book Losering. They are both well written. I don’t think either one of the authors knows the real Ryan Adams because i doubt Ryan Adams does. But he is growing up.
And i was hoping he could stay married to Mandy Moore. Now i just hope he stays alive. I really think he’s amazing. I wouldn’t want any of my nieces to date him. I don’t want him in my family. I wouldn’t want to be in his band. But i am glad he is making music. He’s one of the best.
I read Losering earlier this year about Ryan Adams. I had read many articles about him too. He is a musical mercurial genius and a total brat. I had long heard about his antics at live concerts so i never had a desire to attend one, but i always anticipated his next record, and like his concerts, which were hit or miss, i passed on buying a few of them, Rock N Roll, the Taylor Swift 29 which i feel was meant as sheer mockery and him being an asshole, though i guess from some, it worked.
This book is written by his tour manager and is a first hand account of his dealing with Ryan. I don’t know how O’Keefe didn’t suffer some sort of heart attack trying to keep Ryan in line. I’m glad for him he got out. This book reads similar to Menconi’s book Losering. They are both well written. I don’t think either one of the authors knows the real Ryan Adams because i doubt Ryan Adams does. But he is growing up.
And i was hoping he could stay married to Mandy Moore. Now i just hope he stays alive. I really think he’s amazing. I wouldn’t want any of my nieces to date him. I don’t want him in my family. I wouldn’t want to be in his band. But i am glad he is making music. He’s one of the best.
January 8, 2020
A great snapshot of life on the road in the early 90s as part of an upcoming band and their team. O'Keefe comes across as no-holds-barred honest, and he finds himself to be the conductor on an ill-prepared train that we might say had no business getting onto the tracks in the first place.
You always hear about the time before a band breaks being the best time for them. Here, O'Keefe has that front and center. From bedrooms to tour buses. From cheap beer to all you can drink. From local nobodies to hanging out with rock royalty. As the Whiskeytown legend grew, Ryan Adams wanted out. The behaviors are concerning, but given Ryan Adams' reputation, these stories are hardly surprising--self-destructive, mercurial, temperamental, and absolutely childish. If you're a fan, it's worth a read to get O'Keefe's perspective on what went down in Whiskeytown.
I often struggle to separate an artist from his work, and I truthfully struggle to listen to Ryan Adams at times. He is a great songwriter, and I admire him greatly in that regard, but stories such as these do not paint him in the brightest of lights. The more recent media stories about him are further troubling, but I hope he is able to find whatever it is that he's looking for, and that anyone affected is able to gain some measure of peace.
You always hear about the time before a band breaks being the best time for them. Here, O'Keefe has that front and center. From bedrooms to tour buses. From cheap beer to all you can drink. From local nobodies to hanging out with rock royalty. As the Whiskeytown legend grew, Ryan Adams wanted out. The behaviors are concerning, but given Ryan Adams' reputation, these stories are hardly surprising--self-destructive, mercurial, temperamental, and absolutely childish. If you're a fan, it's worth a read to get O'Keefe's perspective on what went down in Whiskeytown.
I often struggle to separate an artist from his work, and I truthfully struggle to listen to Ryan Adams at times. He is a great songwriter, and I admire him greatly in that regard, but stories such as these do not paint him in the brightest of lights. The more recent media stories about him are further troubling, but I hope he is able to find whatever it is that he's looking for, and that anyone affected is able to gain some measure of peace.
January 11, 2019
O'Keefe gives us intimate access to the wild ride of all the brilliance and childish insanity that took place between Whiskeytown's Strangers Almanac and Pneumonia, the ruined shows, the fights, the drunkeness, the creative drive, the friendships built and busted, the hilarity, and the mundane endlessness of the road. It's not a full bio of the band or Ryan, just the insights from O'Keefe's time managing the road tours and Ryan himself for a little while before fate and major label players took control and sent Ryan off to his incredible solo career. At times the story gets a little jumbled but O'Keefe gives us a pretty clear narrative and paints an honest picture of Ryan as a powerhouse talent who doesn't always do a good job (or any job at all) at keeping his shit together, but we see him develop and grow up some here, and as we all know, for all his ups and downs, his talent has kept him afloat through a lot and continues to do so. As a fan this was a fun read and it's recommended for anyone else who has enjoyed the journey as a listener.
February 27, 2022
O'Keefe (with support from rocker/writer Joe Oestreich) turns in a solid story of life on the 90s rock and roll road, and a well-realized profile of Pre-Totally Famous Ryan Adams. The book isn't fancy, but it was a fun Sunday read if you like that kinda thing (I do).
That Adams's unchecked manchilding turned abusive—well, not surprising. I saw Whiskytown many times and whoa man did I get tired of the whole but-he's-a-GENIUS-routine. It was a real circle jerk.
I give O'Keefe props in that he convinced me Adams really has (had? is Adams ded?) that talent you can't fake. I never saw those shows. (Backsliders BTW, all aces every show). And he made me remember the kooky drunk kid at the bar mouthing off in this way that made you like him, even as you felt sorry for anyone who had to deal with him.
Bless yer hearts.
That Adams's unchecked manchilding turned abusive—well, not surprising. I saw Whiskytown many times and whoa man did I get tired of the whole but-he's-a-GENIUS-routine. It was a real circle jerk.
I give O'Keefe props in that he convinced me Adams really has (had? is Adams ded?) that talent you can't fake. I never saw those shows. (Backsliders BTW, all aces every show). And he made me remember the kooky drunk kid at the bar mouthing off in this way that made you like him, even as you felt sorry for anyone who had to deal with him.
Bless yer hearts.
August 2, 2018
I liked this book a lot even though I agree with some of the criticisms. It's not great storytelling and it often portrays Ryan as an incorrigible, little shit. That aside, fans of his will come away mostly unfazed in their opinions of him. Ultimately, this is a book for the fans of Whiskeytown, a look back to something that was almost awesome and crashed under the weight of immaturity. Still worth a read if you remember that scene and want to be taken back to remember a time when some really cool bands were cutting their teeth in the industry and taking us away from the Seattle malaise and the uber-pop of the decade.
February 4, 2020
I was a charter member of the No Depression alt. Country movement, so this book brought back many memories and name checked several people I knew or was connected to. It’s a quick easy read, but very interesting and fun and 100% rock and roll. Highly recommended for any one who is a fan of the genre, not just Ryan Adams. Adams doesn’t get off easy, but the author clearly has a ton of respect for his talent. And probably more respect for him as a person than he deserved at the time.
June 29, 2018
About a fun as a song about smoking Crack
Great stories and anyone who has seen the band or a strange RA show can really find those stories to be true. And on the flip side anyone who has seen a greater RA/Whiskeytown show, has felt that magic. A fair interpretation of the raise and fall of Whiskeytown.
Great stories and anyone who has seen the band or a strange RA show can really find those stories to be true. And on the flip side anyone who has seen a greater RA/Whiskeytown show, has felt that magic. A fair interpretation of the raise and fall of Whiskeytown.
July 23, 2018
When I finally sat down to read this, I read it all the way through in a day. It’s engaging and seemingly honest. O’Keefe’s experience and presumably Oestreich’s polish produced some highly enjoyable prose. Maybe the closest you can get a front row seat to Whiskeytown’s heyday, until or unless Ryan releases his own account.
August 7, 2018
This is a really quick read. I didn’t know much about the Whiskeytown years and this was at least an eye opening reveal of the chaos underlying Adams’s early years. Apparently it’s pretty thankless work to corral a young, energetic, often drunken genius. I would’ve loved to have been a passenger for a little while, though.
August 12, 2018
Interesting for fans of Ryan Adams
Reminds me a lot of the recent book about the replacements. An enjoyable read and I interesting to read takes of Ryan Adams before he was a big deal. Perhaps not essential but if you enjoy reading tales of the prototypical rock n roll lifestyle you'll enjoy it.
Reminds me a lot of the recent book about the replacements. An enjoyable read and I interesting to read takes of Ryan Adams before he was a big deal. Perhaps not essential but if you enjoy reading tales of the prototypical rock n roll lifestyle you'll enjoy it.
March 30, 2019
I bought this a week before the Ryan Adams articles hit the news, and honestly didn’t want to read it at that point. Suffice it to say that Adams is about what I expected him to be. The book is written well enough, but I can’t imagine wanting to read about Adams at this point unless you are interested in car wrecks.
July 24, 2022
Interesting read that Chronicles the beginnings of the career of the genius punk troubadour. Man, he was a F-up, but you can’t deny the talent. I could relate because I too tore managed a small band With a prima donna singer and drug habits in a 15 passenger van with a trailer… A couple of times I broke into a cold sweat while reading.
September 29, 2019
Full spectrum
Wow! By Chapter 17, I never wanted to listen to Ryan Adams ever again, but by the end of 19 O’Keefe did a great job of redeeming him enough to give up on that notion (a bit). Great read!
Wow! By Chapter 17, I never wanted to listen to Ryan Adams ever again, but by the end of 19 O’Keefe did a great job of redeeming him enough to give up on that notion (a bit). Great read!
July 10, 2022
O'Keefe confirmed my impressions of Ryan Adams being a self centered whinyass punk kind of kid with extreme talent. His lack of gratitude for those around him is apparent. Informative about his lack of touring passion. Recommended to those who want to know more about this gifted song writer.
April 9, 2023
If you like Daisy Jones and the six, you will love this book. Thomas O'Keefe provides musical history while traveling with a genius of the 90s music scene, Ryan Adams. I am grateful to have seen whiskeytown live in Seattle, even if it was not their best show.
November 10, 2018
Must read for fans of Ryan Adams and/or Whiskeytown. Enjoyable for any music fan.
August 5, 2018
Can’t help but compare this to Bob Mehr’s Replacements book, only Adams’s debauchery doesn’t make for nearly as good a story or come across as endearing.
April 24, 2019
I love his music, but man, this guy is a douche.
October 4, 2019
Worth the couple hours it takes to read. I didn't learn anything that wasn't in "Losering", but its interesting to see the day to day of a band in that stage of their trajectory.
February 21, 2020
Being credibly talented does not seem to lend itself to being a good human being. Not being a good human being is not necessarily illegal...
April 15, 2021
A good read - I like Whiskeytown's albums and detest Ryan Adams. This just reinforces that...
Displaying 1 - 30 of 35 reviews