Whiskeytown’s tour manager had a front row seat to Ryan Adams’ genius, and his turmoil

Whiskeytown formed in Raleigh in 1994, eventually dissolving in 2000 as lead singer Ryan Adams, front, pursued a solo career. A new book by Thomas O’Keefe, the tour manager for the band during its run as the pre-eminent “it” band, chronicles the band’s stories in “Waiting to Derail: Ryan Adams and Whiskeytown, Alt-Country’s Brilliant Wreck.”
Whiskeytown formed in Raleigh in 1994, eventually dissolving in 2000 as lead singer Ryan Adams, front, pursued a solo career. A new book by Thomas O’Keefe, the tour manager for the band during its run as the pre-eminent “it” band, chronicles the band’s stories in “Waiting to Derail: Ryan Adams and Whiskeytown, Alt-Country’s Brilliant Wreck.” NEWS & OBSERVER FILE PHOTO

Twenty-plus years removed from Whiskeytown’s heyday, the shadow of the Raleigh-based group still hangs over the local music scene, perhaps most heavily on any band that attempts to have a sound that is similar to their alt-country ancestors.

Bandleader Ryan Adams’ antics upon local music venue stages have become the stuff of legends. On more than a few occasions, the stage met the end of the singer’s guitar.

Fans of the band and Adams often have questioned whether these moments were legitimate angry outbursts or perhaps calculated moves by a musician determined to be as much of a rock star in reality as he was in his own head.

If anyone can give us insight into who Adams truly was back then, it’s Thomas O’Keefe, the tour manager for the band during its run as the pre-eminent “it” band within the burgeoning genre known today as Americana.

O’Keefe came on board with the band as it signed a major label contract under the Geffen Records umbrella to release what became the album most synonymous with Whiskeytown — 1997’s “Strangers Almanac.”

He had a front row seat to the turbulence that was life on the road with Adams, with his resulting chronicle of the time in the book, “Waiting to Derail: Ryan Adams and Whiskeytown, Alt-Country’s Brilliant Wreck,” co-written with South Carolina-based author Joe Oestreich and published June 26.

Waiting to Derail Cover.jpg
“Waiting to Derail: Ryan Adams and Whiskeytown, Alt-Country’s Brilliant Wreck,” by Thomas O'Keefe and Joe Oestreich, tells stories of O'Keefe's time on the road with Whiskeytown before it broke up. Skyhorse Publishing

The book sheds light on many of the incidents that happened during O’Keefe’s three-year run with the band, from the time of “Almanac”’s release to their ultimate dissolution in 2000 as Adams embarked on a solo career.

The News & Observer spoke with O’Keefe about his experience, and why Adams continues to avoid North Carolina, before he stops at Raleigh’s Schoolkids Records July 23 to share some of those stories. O’Keefe, now the tour manager for Weezer, is in town for Weezer’s show July 24 with the Pixies at Coastal Creek Credit Union Music Park at Walnut Creek.

Q: The legend of Whiskeytown is still a strong presence within the Triangle music scene, with so many bands in the area striving to reach that level of acclaim. Was the impact they were having at the local level noticeable to those working within the band at the time?

A: I would say that anytime an artist within a certain town or scene signs with a major label, all the other bands in the area are immediately “haters,” and it’s clearly rooted in envy. Of course, Ryan hasn’t helped anything by snubbing North Carolina for the last 12 years. It helps contribute to those hard feelings more than anything else. (Editor’s note: Adams’ last show in North Carolina was June 8, 2005, at Meymandi Concert Hall in Raleigh.)

To me, Raleigh, North Carolina, is the place where all of his original supporters were from; that’s where the first people who supported Whiskeytown, loved the band and got in their cars and drove on Friday nights to go see them are from. It just astounds me that he is — for some crazy reason, which I understand, but it’s hard to explain — he just wants to punish the town, if not the whole state.

He hasn’t played a show in the entire state in years, and as someone who makes his living as a tour manager (currently for the rock band Weezer), I can assure you that isn’t a coincidence. No band goes out on a tour of 40 cities in the U.S. and skips Charlotte and/or Raleigh accidentally.

Q: Can you try to explain why you believe he wants to punish Raleigh?

A: He loves a nemesis, a battle, a foe. Whether it’s him battling the band the Old 97’s (whom Adams would call “the Mold 97s” onstage while opening for them) 20 years ago, or whether it’s him battling The Strokes (band members have accused Adams of facilitating guitarist Albert Hammond Jr.’s heroin addiction) in recent years, he needs (someone) to have a diatribe against. He is kind of powered and fueled by drama, and in absence of naturally occurring drama, he’s able to create it. That’s really the best way I can explain it, and he’ll always have his stance of “I’m just not going to play North Carolina again, ever” to fall back on if nothing else is at hand.

Q: Whiskeytown was always described as half-band, half-soap opera. Ryan’s alcohol abuse at the time has always been pointed toward as a factor in this, but how much of the drama surrounding the band do you feel like would have still been there, even if he hadn’t been drinking?

A: The two are unrelated. The entire soap opera aspect of Whiskeytown had nothing to do with his alcohol or drug intake. Ryan Adams is absolutely one of the smartest people I’ve met in my entire life, and he knows you get more press by fighting with the Old 97’s, he knows there’s more press when you fire the entire band onstage four days before the tour is over. Even at a young age, he was very self-aware and calculated (about press), and it was part of his genius.

Q: You’re alluding to the famous Kansas City show that occurred in September of 1997, where Adams fired every member in the band that was playing that night onstage during the show, short of fiddler Caitlin Cary. He and Cary ended up finishing the tour, as a duo, to rave reviews. What can you tell us about that night, and why didn’t they just continue as a duo after that run of shows?

A: They were playing a relatively normal show in Kansas City that night, and toward the end, he started changing the lyrics of one of the songs, which he would do sometimes. But this time just felt negative. He was complaining about the music industry, and complaining about being in a band, and it turned into this diatribe about everything he hated.

And he kept playing and playing, and I’m on the side of the stage trying to figure out what was going on. They did a huge, almost (heavy metal) ending to the song, and he took his guitar off and told everyone in the audience, “Go home and get on the (expletive) internet and tell all your friends that you just saw the last Whiskeytown show.” He walked toward me with a very stern look on his face, which was unusual, and said, “I have to be back in Jacksonville, North Carolina, tomorrow, and I don’t care how you do it.”

So we ended up staying up all night with him, and then his managers took over the next day, and we ended up talking through the whole process of deciding to rent a minivan and do the final three shows as a duo. While we were driving, the three of us — me, Caitlin and Ryan — made all the phone calls at gas station pay phones and (recruited new band members), while the fired members of the band were in the RV driving the thousand miles from Kansas City to Raleigh.

I don’t think Ryan really considered the duo idea very seriously. I know that there were some positive reviews of the duo shows, and there are some (recordings of the concerts) floating around out there somewhere, but there was no serious talk of the two of them continuing on by themselves.

I do believe — and this is important — that the elemental formula of Whiskeytown was always Ryan and Caitlin. I don’t think Ryan Adams has made an album better without Caitlin than the ones he made with her. ... It does bum me out that he hasn’t had Caitlin do some stuff on some of his solo records.

Q: Why — once the number of current and former members of Whiskeytown approached 20 — were so many musicians still willing to sign on to work beside Ryan?

A: The thing about Ryan is you immediately recognize that he is incredibly talented; he is more talented than anyone you could possibly meet in your life. He’s also extremely smart, and when he’s in a good mood, he can be one of the absolute most charismatic and funny people you’ll ever meet. He is a great person that you would want to be in a band with, because he’s extremely prolific, and I’m certain if he took an IQ test, he’d be off the charts.

I think the music, and the greatness of his songwriting ability, is what lured people into wanting to be in the band. The (band firings) did reach a point of ridiculousness, and the band did become a revolving door to a certain extent, but there are many more stories in the book about how incredible it was to have a front row seat every night to watch a genius at work.


Who: Thomas O’Keefe, reading from “Waiting to Derail: Ryan Adams and Whiskeytown, Alt-Country’s Brilliant Wreck”

When: 7 p.m. July 23

Where: Schoolkids Records, 2237 Avent Ferry Road, #101, Raleigh

Cost: Free. Profits from all book sales will go to INTERACT, a Raleigh-based organization that provides a safe place for victims of domestic violence.

Info: 919-821-7766 or

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