Waiting to Derail: Ryan Adams and Whiskeytown, Alt-Country's Brilliant Wreck / Book Review & Interviews with Authors Thomas O’Keefe & Joe Oestreich - by Jeremy Porter

(co-author Joe Oestreich will appear at a reading & discussion event for Waiting To Derail: Ryan Adams and Whiskeytown at Gramercy Books, 2424 E. Main Street, Bexley, OH, this Friday, July 13th at 7 pm) 


They don’t make rock stars like they used to. There’s a scene near the end of “Waiting to Derail” where the author, Whiskeytown’s former tour manager Thomas O’Keefe, then managing the adult-rock mainstays Train, walks into the hotel lobby two minutes late and gets a visual scold-down for his tardiness. What happened to the Stones going on when they felt like it? Or W. Axl Rose taking the stage well after midnight? Or Shane MacGowan showing up blind drunk or not bothering to show up at all? Even Billie Joe Armstrong stopped having tantrums a couple years ago after a highly-publicized meltdown at a festival.   

Maybe that was the bait that made me want to get my hands on this book as soon as I could. Of course I’ve heard the stories too: the meltdowns, tantrums, intense (and annoying) self-awareness, but man, I also love those songs. Whiskeytown sure had the country thing down, but they could also rock like anyone, and it was the definition of Alt-Country when Alt-Country was exciting, before the tag became another overused, over-hyped, over-practiced genre-label, joining the ranks of Hair Metal, Pop-Punk, Grunge, Shoegaze, and a hundred others. Before it was applied to too many bands putting forth a watered-down version of a few pioneers, lacking the originality to come up with their own thing.  

I first heard Whiskeytown right around the time O’Keefe started managing them. They’d signed on with a company called Jacknife for promotion and management, and my friend Jenni Sperandeo (Jacknife founder and a key player in the book) gave me an advance copy of “Strangers Almanac” on cassette with stern instructions to listen to it. She assured me I would love them. At first, I didn’t. I thought they were a passable rip-off of Uncle Tupelo (another band Jenni turned me onto, after they’d broken up), so why would I listen to that when the UT catalog was still fresh to my ears? A few years later I told Jenni she was right about them. I didn’t see it at first, but before long I came to realize that they were incredible, and on their own plane altogether. Sadly, the band was over by then, and the wreckage is laid out before us on the pages of this book. 

The story carries itself along the timeline of a young band thrust into the rockstar life of traveling the country in a big tour bus, but that’s where it differs from other indie-rock bios. There’s no playing to three people and the bartender, no sleeping on the floor of the local support band next to a dirty kitty litter box, no sex with the cute, drunk co-ed fan on the big university campus, no cheap-ass-speed-cut cocaine making everyone agitated. None of that “Remember when we did that crazy thing I would never do now?” stuff that most bands also refer to as “paying your dues.” If Whiskeytown went through that phase, it was before O’Keefe signed on, or he purposely left it out, and the almost immediate jump from no one to someone might help to explain why Adams was unable (or unwilling) to adapt gracefully. Throw in the expectations around the record & the tour, and the age of the kid whose shoulders they were stacked on, and it’s almost surprising they were able to keep it together as well as they did.

Still, It’s not a pretty portrait, and though there are plenty of moments you empathize with him, they’re not quite frequent enough to make you like him more than you did before you picked up the book. He comes off as the kind of polarizing rock star that seems absent from today’s musical landscape. He’s part genius, amazing artist, musical sorcerer, and part spoiled brat, annoying drunk, and selfish, entitled jerk who “needs to get his teeth kicked in” (as Paul Westerberg once said, and later played down). It's downright complicated, and O’Keefe spends a lot of the book, and apparently spent a lot of the time he was with the band, trying to reconcile one side with the other, trying to convince himself that it was all worth it.

The story follows the band from the weeks before “Stranger’s Almanac” came out, the record that was supposed to change everything (it didn’t), until the band played their final show in 2000. It’s chock-full of great stories about being on tour - the mundane and the crazy - delivered in an intelligent, introspective narrative that rises above the majority of this genre of literature, that is too-often written in a much more adolescent voice. Co-author Joe Oestreich certainly has something to do with that, having penned a great book with a similar cadence about his own band Watershed’s adventures called “Hitless Wonder: A Life in Minor League Rock and Roll” in 2012. 

Maybe it’s because I’ve done my share of time in a van, dealing with bandmates and situations I didn’t always find enjoyable, but I could relate to the yin and the yang of the story - the good times & the bad, exciting & boring, drunk & sober, brilliant & terrible, agreeable & defiant. That’s the theme that keeps coming back. Is he a genius or an asshole? Are the sporadic fun times and great shows worth the frequent agitation and disastrous shows? In my experience, that ebb and flow is always present on the road, and always a challenge, but I can only imagine the vast difference between the manic Ryan Adams on his best nights and his worst.

I’m sure that O’Keefe doesn’t regret those years, but I bet he was glad when they were over. Certainly a lesser man would have bailed well before he was forced out. The events were well-chosen and balanced to show the line between the two sides of a young man trying to sort it all out in a head that was often clouded with alcohol and so constantly full of incredible songs that it had little room for anything else, including the impact his actions had on the people around him and those who believed and invested in him. It’s a well-told, detailed, engaging story that reminds us that rock and roll can be the greatest party on the planet some nights, but it can be a downright drag on others. It’s not always pretty, it doesn’t always run on a clock, and there’s always some sort of carnage left in its wake.  


INTERVIEW with author Thomas O’Keefe

JP: You seem like a pretty busy guy, and it seems like a lot of work went into this book. Why did you decide to write it, and did it turn into something more than what you bargained for?

TOK: I had always known I was going to do it, even back then I knew. I met Joe 20 years ago, and we’d discussed writing it for many years, then “Hitless Wonder” came out… Ryan is more popular now than ever before, but the timing is pure coincidence based mostly on my availability and Joe’s availability, our schedules clearing up. We spent about three years from the time we started; acquiring the book deal, working on the book, to the book coming out.  

It wasn’t really [more than I’d bargained for]. Joe had written several books and helped me through the process - what it takes to make a book great. It was an extremely big learning process. I learned that in order for a book to be really great, the right person has to write it. In this case, I’m just the right person. I saw Whiskeytown more than anyone else. I lived it, saw it, remembered it. I don’t mean for it to sound arrogant, but no other person on Earth could have written this book.

JP: When I first heard about the book, several months before it came out, I’ll confess that I was a bit skeptical, expecting something a bit more tabloid or tell-all in nature. Maybe it’s the level of celebrity that Ryan Adams has now or whatever…  Reading the book, I don’t think it really comes off like that, but were you cognizant of that angle, and did you intentionally take it a in direction to avoid (or embellish) some of that stuff?

TOK: To me it’s more the story of this ridiculous young genius, with the good and bad aspects of him, and those of us who first realized he was that guy, and we were the ones who were trying to get him to do the right thing.

Imagine if you were the person who saw Bob Dylan’s first five years - would you want to write a book about it or just let it float away and be lost in the wind, you know? Early on in the book there a part where I realize that he’s this amazing, once in a generation songwriting kid who could just churn out songs almost like it was a burden, one after another after another. I thought, this is like being with Bruce Springsteen when he was 23 years old, or Bob Dylan, or Tom Petty or whoever, and I believe that Ryan Adams is as good as those guys I just rattled off.

We went out of our way to not make it a “Ryan is an asshole” book, but to show how he was tough to deal with, but also that he was insanely, insanely talented. It’s not some kind of “hit piece” aimed to get him or anything. I certainly don’t have any axe to grind, or whatever. You know, he did that stuff, and most of it is public knowledge - the Fillmore show and the bus in Seattle. I feel like it conveys what we wanted it to convey. There was never any intention to make the book negative or tabloid.  

JP: I’m in Michigan, and that Lansing show was legendary in these parts. I have friends who were there. One friend told me the first words out of Ryan’s mouth on stage were “I hate playing places like this.”  You covered it fairly extensively in the book, but I’m curious if there are any juicy tidbits you left out in editing that didn’t make the cut?

TOK: Yeah, something to the effect of “You guys are the sports-bar assholes who used to beat me and my skateboard friends up when I was a kid.”

You know, I think it was all in there, at least as far as we remembered it. The amazing part of that story, I thought, was the guys who were throwing tomatoes at us. I mean - who goes to a rock show to see a band and coincidentally has two grocery bags full of tomatoes? That’s the part I don’t understand.  

The thing about Ryan that you have to understand, like the sports bar in Lansing or the ski resort in Aspen. Most of his lashing out and destroying those shows, the reason for it was rooted in his punk-rock ethic that this band shouldn’t be playing these kind of places. He wasn’t mad at the people of Lansing or Aspen, he was mad because “Why is our band playing a sports bar?”  That was not where they belonged.

The punk rock guy in me loved watching him smash everything, but then the tour manager guy in me had to go clean up the fucking mess afterwards, which I hated, and which was usually difficult, but his reasoning just came from what he thought that band should be and where he thought they should be performing. His reasoning was not out of line, he just wanted to make sure that they stayed credible.

JP: I was glad when you wrote that you later heard that Mac’s was actually a cool place, run by people who love music, because it is, and whatever it lacks in a healthy PA system and rock & roll ambiance, it makes up for in character and spirit when the music starts. Having played (and am still playing) a circuit where these kinds of bars are fairly common - sports/dive bars doubling as rock clubs that aren’t as equipped as full-out music bars - I was kind of surprised that it seemed like so much of an anomaly to the band. Was it that out of the ordinary? Or was it more just the mood of the night and a reason to stir up some shit? 

TOK: Keep in mind that their touring experience at that moment was fairly limited. They’d played everywhere in Raleigh and done some tour dates with the previous record leading up to this, but yeah, the moment he walked in he just wanted to know “Why are we here?”  

JP: It sounds like you talked to just about everyone except Ryan. Can you talk just a little about how you went about tracking down some of the key players in the story?  Anything crazy or out of the ordinary stick out?

TOK: Well, not really. I mean, yeah I talked to all of them, and a few of them I had to track down, but I’m still friends with most of them. 75%, 50% of them are in my cell phone, so I just had to get on the phone with them and do it, or I was Facebook friends with them or something to that effect. I saw Phil when I was on tour in Seattle last year, and I was on tour in Austin so I visited Jenni Sperandeo, so for the most part it wasn’t that hard.

JP: Even though you were there, with a front-row seat, I bet you learned a lot about those events and got a different perspective in the process.  Care to talk just a little about how your feelings, memories, or that perspective changed from the time you started the book and the time you were finished?

TOK: I did an interview the other day and the guy asked me “What was the most surprising part of talking to everyone else?” I thought about it for a second and I told him the most surprising part was how little everyone remembered. I spoke to every single band member, the crew members, the bus drivers, the managers - I spoke to everybody - and the combination of all of those discussions added about three to four percent to the book.  So the reality is that had I not spoken to anyone, the book would have been 97% the same.

JP: There’s a scene in the book where you take GG Allin to a corporate Christmas party for a company you were working for. It’s an interesting segment, but I couldn’t stop wondering what led up to that - I mean, I understand the history around it and stuff - but more the decision to actually take him to that party.

TOK: Well, that was a decision made by two guys - myself and Jeff Clayton from my old band [Antiseen]. We were two 26 year old idiots. It’s astounding to me me today that we did that.

JP: Yeah, I probably wouldn’t have done that.

TOK: Yeah, me neither, today. 54 year old Thomas wouldn’t have done that, but 26 year old Thomas didn’t give a fuck. We probably should have been fired. We were expecting to get called into HR and get a taking to or something, but no one said a word to us. I’m still shocked today that we did that. I’m sure Jeff would say the same thing.

JP: I’ve heard notions that Ryan is not thrilled with the book. Have you heard from him since it came out? Any reaction from him at all?

TOK: No, he declined to talked to me, which I expected him to do, because Ryan only cares about what’s moving forward. If you review his history, he’s always shit-talking his band by the end of the tour. “My next band is going to be way better, my next album is going to be way better.”  He never looks back, he only looks forward.

I think it’s a fair, accurate depiction of those days, and it’s great that somebody documented that. He should be happy as far as I’m concerned, but I’m sure that he will at least publicly say that he doesn’t like it.

JP: He certainly is aware that it’s going on…

TOK: Oh, he’s very aware of it. I did an in-store at a record store in Houston a couple weeks ago and they posted a picture to Twitter and copied him on it, and he blocked the record store 10 minutes later, so I am 100% sure that he’s aware of it, but I don’t know if he’s read it or whatever.

There was a book that came out about Whiskeytown about 10 years ago, written by a sort-of super-fan, local writer out of Raleigh, and he made the mistake of calling Ryan first. Then Ryan called all of us “Don’t talk to him, don’t talk to him!” and I told Ryan that I wasn’t going to talk to him because I’m saving all this shit for my book! Ryan said “I’m not afraid of your book, that’s cool.”  And I said “You shouldn’t be afraid of it!” And he still shouldn’t be afraid of it. It’s the story of a young genius and those of us who tried to help him keep his shit together so that he would become the guy he became.

JP: Any reactions from any of his fans?  

TO: Of course the main people who have read this book so far and I’ve gotten feedback from are the super fans - they bought it the day it came out because they couldn’t wait - and I’ve gotten 100% positive feedback from them, not one negative. I think they all know that he’s difficult, know what I mean?  

JP: Can you talk a little about what role Joe Oestreich played in the writing of the book? How did that dynamic work?

TO: Absolutely. You know, Joe is kinda like a brother from another mother kinda thing. If I had grown up in Columbus I probably would have played in his band. He and I read from the same book, so to speak, if that makes sense. Joe was my only consideration for doing this. His book “Hitless Wonder” was outstanding and really great and I loved the way it flowed. There’s no way on Earth I could have done this book without him. We worked great together. He’s a college professor so he’s a great listener. We powered through it and I couldn’t imagine doing it with anyone else.

JP: So you’re out on the road with Weezer now, right? That’s a good gig! What’s next for you - do you have the author bug and another book in you?

TO: That’s a great question. I don’t know. I have no plans of writing another rock book. Like I said earlier, I was the right person to write this book, but I have no interest in writing about any of the other bands that I’ve worked with. I think my next book is going to be about squirrels and hippies. I have a concept in mind about it, and I’ll leave it at that.  


INTERVIEW with author Joe Oestreich

JP: Hey, Joe! Been a couple years, eh? My first question is maybe a bit obvious... This is clearly Thomas' story, he's the one that lived it, but I couldn't help to feel that it read a lot like "Hitless Wonder" - not so much in story, but in voice. What was your role, and/or what was the dynamic in the writing process?  

JO: This is definitely Thomas' story, and he’s probably the best storyteller I know. He has a great memory, and his stories are packed with quirky, real-life detail. The kind of stuff that only a first-rate storyteller notices. Plus, he’s been telling these stories for twenty years, so he’s got them dialed-in. My role was just to help bring the tales to life on the page. I saw myself as something like a record producer. A record producer’s job is to help turn the artist’s vision into an actual album, right? My job was to help turn Thomas’ vision into an actual book.

Now, regarding similarities to my first book - "Hitless Wonder" - again, go back to the record producer comparison. You and I have both worked with producer Tim Patalan at The Loft in Saline, Michigan. Even though our songs are different and our playing styles are different, everything that comes out of The Loft has a distinct sound: because of the room, the console, because it’s been filtered through Patalan’s sensibility. So I guess it makes sense that everything that I work on would reflect some of my sensibility.

JP: I interviewed Thomas too, and told him that it had to be a lot of work to write this, especially with all the players involved, and it seems like he talked to them all but one. Were you involved in that part at all? What were some of the challenges you had in writing the book?   

JO: The “one” you mention is Ryan himself. We reached out to him several times, but he made it clear that he wasn’t interested. Obviously we wish that we could have gotten his side of the stories, and maybe someday he will write his own book. I hope he does. I’m sure it will be great. But our book was never meant to be Ryan’s story of Whiskeytown. It was always meant to be Thomas’ story of Whiskeytown.

Thomas did talk to every person that played in the band, and as you know, that’s a lot of people. We’re talking Spinal Tap drummer quantities. Plus he spoke with all the crew guys, soundmen, and bus drivers. We also did a ton of research into how magazines and newspapers covered the band at the time. Believe me, we had a ton of material. And that was the biggest challenge: whittling down the material so that it didn’t become redundant. Like, how many stories of Ryan being a screw-up do you have to depict so that the reader can appreciate the depths of Ryan’s screw-up-ness? We tried to keep the narrative tight and fast, and that meant leaving out some good stuff.  

JP: You mention in the end credits that you met Thomas at a Watershed show in Raleigh and Ryan was there, at least briefly.  Did you have any other encounters with the band back when both Whiskeytown and Watershed were active? Were you a fan? Any of the other key players?  

JO: I was a fan and I am still a fan of both Whiskeytown and Ryan. I remember hearing “16 days” on Columbus’s CD102.5 (the station then was called CD101) and loving it. I was blown away when I found out that Ryan was only 22. And though we didn’t meet Ryan and WT back then, Watershed was still touring heavy, and we played many of the same venues WT was playing, right around the same time. For instance, in the book we tell the story of the time Ryan caused a near riot at Mac’s Bar in Lansing. Watershed played Mac’s about a week after that happened. When we got there, all the bar employees were still talking about Whiskeytown. And they were pissed. The fact that I had been there in real life helped me to add some detail to Thomas’s story about that night.  

But, yeah, I’m a fan. I think "Strangers Almanac" is a masterpiece, and Ryan has made several more albums that I love. My favorite is "Rock N Roll." I dig a bunch of songs off recent records like "Ryan Adams" and "Prisoner." I’m also a fan of WT fiddle player Caitlin Cary. I saw her post-WT band Tres Chicas at The Continental Club in Austin for SXSW 2006. They were incredible. And sometime WT drummer Jon Wurster is so freaking great and versatile. Superchunk, Marah, who doesn’t he play with?

JP: I've been a WT/RA fan since the story started, before "Strangers Almanac" came out, but I don't think this book is going to make anyone run out and buy his records. How did you feel about him/them when the book was finished, (assumingly) knowing what you didn't know going in?

JO: I hope the book does make people want to go out about buy his records, because readers will learn more about both Ryan-the-person and Ryan-the-persona. But it’s true that in the book we don’t talk a ton about the music itself. I think that’s for two reasons: 1) The music is almost never the most interesting thing about a musical artist, and 2) We figured that the core audience for this book would probably be people that already owned a Ryan Adams record or two. No need to tell them what the songs they already love sound like. We do, however, talk in some detail about the significance of WT and other alt-country artists at that time. We give larger context to the “y’alternative” movement and to issues like “What makes an artist authentic?” And we talk about what Ryan’s songwriting process looked like from Thomas’ perspective.

Like lots of Ryan fans, I have a hard time keeping up with his overwhelming productivity. He’s like The New Yorker magazine. Somehow a new one keeps coming every week, faster than you can read them, and they just pile up on the coffee table. Sometimes I wish Ryan would release fewer records; but take more time on them. I guess I’m saying I wish he had an editor. But after working for two years on this book, I now have a huge appreciation for his sense of urgency. It seems to me like Ryan always feels the clock ticking, like he feels that he needs to be as productive as possible during the finite minutes he has left. Write every song he can. Make every record he can. He doesn’t have time to be precious with every little decision. He’s just going to get the work done. Keep cranking. I get that. I respect that.

JP: Another thing I asked Thomas about was something that came to my mind as soon as I heard about this book many months ago: that it had potential to be a sort of tabloid story, given Ryan's celebrity & status now, and the legendary shit he's known for.  I don't think it comes off that way, but I feel like it could have without much effort. For example: there are a few vague references to drugs being present, but nothing harder than weed is ever specifically mentioned in detail. Did you intentionally avoid (or embellish) that tabloid side of the story (not just the drugs, but....) at all in a quest to be honest, sell books, make it as interesting as possible, avoid controversy, etc?

JO: People are complex, man. And Ryan is especially so. We wanted to present the truth of him in all his complexity. Genius songwriter? Yep. Childish, self-involved screw-up? Yep, that too. To gloss over either side would be a disservice to the truth. Plus the two sides are connected, maybe even symbiotic. Ryan wouldn’t be such a self-aware and prolific songwriter if he wasn’t also selfish and self-involved. “Selfish” and “self-involved” is how songs get written.

We definitely didn’t embellish. With Ryan, you don’t need to. In those days he was a walking, talking, story-making machine. You just let what happened speak for itself. Stay out of the way of the material. We don’t spare any details that Thomas knew about, but when it came to drugs, etc., we didn’t speculate about the specifics, for a whole host of reasons: practical, ethical, and legal. From a tour manager’s standpoint, it doesn’t really matter how the artist got too messed up to play; it only matters that the dude can’t play.

Whiskeytown seemed to skip a lot of that "paying your dues" stuff that Watershed certainly went through, and that most bands go through (whether they ever get past that level or not). The way the book read, they were doing odd weekend runs, then they were pretty much in a tour bus and playing big shows. No mention of playing to three people some nights, all that stuff.  The story is easily compelling enough and offers more than enough of its own struggles to make up for that, but to me, that's one of the things that sets it apart. Were you cognizant of that angle, did it strike you as odd too? Did you get any PTSD reading some of the painful road stories?

JO: As Thomas says, Ryan pretty much went from writing songs on the edge of his bed straight to the tour bus. It wasn’t quite that quick and easy, of course, but compared to lots of other bands, Whiskeytown did get signed relatively soon after forming. That’s not their fault. It’s not a fault at all. It just speaks to how great they were. They got signed quickly because they deserved it. They were playing the right kind of music at the right time, in the right town (Raleigh), with a charismatic front man and undeniable songs. That’s the key: the songs. Ryan got signed young because he was writing songs that were way better than most 22 or 32 or 42-year-olds can write. And no PTSD from me. I love reading about bands on the road.

JP: This is your fourth official book (right?) and second rock bio. As someone who pretty much just reads rock & roll books (and menus and road signs), I'm all in.....but why another rock and roll book about a band on the road? Did you at all ponder the "been there, done that" question, or is this something you see yourself doing even more of in the future?

JO: As much as I love reading about bands on the road, this is probably my last time writing about them, unless Dave Grohl wants me to chip in on his memoir. I’d love to do that. If you’re out there, Dave, I’m available (wink, smooch).

JP: And what's next for you? You have a reading/signing coming up in Columbus, no?  What's the next project? Another book? Recording at The Loft?

JO: Yep, I’ll be reading from and talking about "Waiting To Derail" on Friday, July 13, at Gramercy Books in Bexley, Ohio. As for the long term, Watershed has a bunch of new songs that we are working on, and I’m thinking about writing a novel. That seems like the hill every writer has got to climb: and hopefully not die on. 

JP: Thanks for doing this! The book is great and I'm sure it will do well. Talk soon I'm sure!  

JO: Thanks, man!


Jeremy Porter lives near Detroit and fronts the rock and roll band Jeremy Porter And The Tucos.

Follow them on Facebook to read his road blog about their adventures on the dive-bar circuit.  

Twitter: @jeremyportermi | Instagram: @onetogive