Thomas O'Keefe, author of "Waiting To Derail: Ryan Adams and Whiskeytown"...

We recently spoke to Thomas O'Keefe, author of Waiting To Derail: Ryan Adams and Whiskeytown. O'Keefe was the tour manager for Whiskeytown beginning with their first major label tour supporting Strangers Almanac, until their breakup in 2000. The twenty-year veteran of the music industry is currently tour managing Weezer.


As a former punk rocker in the band ANTiSEEN, you seemed to recognize the punk side of Ryan early. And while that attracted you, didn't it also made your job much harder?

My punk rock past actually made my job easier. Ryan listened to my band’s records when he was a kid. It made him slightly more likely to listen to my advice, as in his mind. I was coming from a legitimate place. This was not always the case however…It was a dual edged sword as while he was destroying a show, The Punk Rock dude in me LOVED it but then I realized I was also the guy who has to go and tries to collect the money from an angry promoter when it was over.

Paired with that side of Ryan was a kind of “old soul” side that featured prominently in his songwriting talent. Do you think this dichotomy was an essential component of Ryan Adams and how so?

I believe he is unmatched as a songwriter. The songs come to him with such ease and frequency, it’s almost like witchcraft. I think the important punk rock component is his Indie Rock Cred, That is his most valuable asset and he would never comprise that. He has a Black Flag tattoo.

The real dichotomy was when they played live, When he played a punk rock Whiskeytown show (destroying the show and or guitars) the No Depression/Alt-Country types of the late 90’s were confused. I once told the president of our record label, “If you think of Whiskeytown as a punk rock band, this all makes perfect sense”

You went from road managing Whiskeytown to Mandy Moore. That must have been one hell of an adjustment. What did you learn?

I did her homework during this time and realized I’m still pretty good at geometry…

Since Whiskeytown, I worked with many people from Train, Sia, Third Eye Blind and many others. I currently work with one of my favorite bands, Weezer. Every band is different. Mandy was fun and easy because she was sweet and her parents were out with us and I really liked all of them. Ryan was living at my house in NC while I was out on tour with Mandy in 1999. I didn’t introduce them but, Ryan and Mandy would later marry (and divorce).

What, if any, is your relationship with Ryan now, after the book? Has he read it?

I told Ryan in 2007 I was planning on writing a Whiskeytown book. I felt it was an important story. I saw the band 174 times, I wasn’t drunk and I have an elephant’s memory and I kept notes. I wanted to get the story together before I got old and forgot it myself.

He was cool with it in 2007 but I’ve had little contact with him since. He goes out of his way to avoid everything to do with North Carolina these days and I’m part of those times. He hasn’t played a show in NC since 2005. No band does a US Tour and doesn’t play Raleigh and / or Charlotte. He intentionally avoids the entire state. I don’t understand punishing the state that gave you your start.

I hope he reads it, He should. It’s not negative at all. It’s the story of a young genius and the first handful of people who tried to help him. We were the first believers.

Certainly his restlessness and pace of recording hasn’t slowed down from his Whiskeytown days. What do you think of his post-Whiskeytown work? Do you keep up? Any favorites that match your feelings for “Avenue”?

I think a lot of his solo work is great. However, I still think Stranger’s Almanac remains his high-water mark to date. I believe the important ingredient was Caitlin Cary (Whiskeytown vocals and violin player) The two of them together was the magic of Whiskeytown. I was never a fan of Alt Country. Neither was Ryan. He wrote and played it, but he didn’t listen to it as a fan. While we were on tour, I drove the RV and Ryan sat in the passenger seat, we controlled the stereo. All day long, it was Black Flag, D-Generation and Royal Trux.




Tune into our Spotify playlist Waiting to Derail.




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