Author and Watershed singer/bassist teams up with former Whiskeytown tour manager to pen book on Adams' early, indulgent years

About 20 years ago, Joe Oestreich and his bandmates in Columbus rock act Watershed were playing a Cheap Trick cover at a venue called the Brewery in Raleigh, North Carolina.

“We saw one guy out in the crowd who was loving it, just going nuts,” Oestreich said recently by phone from his office at Coastal Carolina University, where he now chairs the English department.

After the show, Oestreich struck up a conversation with the enthusiastic fan, who turned out to be Thomas O'Keefe, tour manager for Whiskeytown, the Raleigh alt-country act fronted by Ryan Adams that had recently signed to a major label. O'Keefe regaled Watershed with stories about Adams' recent antics on the road, which were already becoming the stuff of rock 'n' roll legend.

Twenty years later, O'Keefe is still telling Ryan Adams stories, and, with the aid of Oestreich, the tales are now set in ink. Last month, O'Keefe and Oestreich published Waiting to Derail: Ryan Adams and Whiskeytown, Alt-Country's Brilliant Wreck. The book charts the alcohol-fueled path of Whiskeytown from just before the release of its 1997 instant-classic, Strangers Almanac, to the band's demise in 2000.

“Thomas is one of the best storytellers I've ever met. He's highly detailed. He's got a great memory,” Oestreich said. In one scene from the book, Adams is hanging out backstage with post-grunge act Seven Mary Three at Milwaukee's Summerfest, and O'Keefe zooms in on the glob of milkshake stuck in Adams' hair. “Those little details that seem maybe meaningless at the time — that kind of stuff makes the story feel real,” he said.

Oestreich, who has previously published a collection of essays, a book of narrative journalism and a memoir (the excellent Hitless Wonder: A Life in Minor League Rock and Roll), likened his role in Waiting to Derail to that of a producer in a recording studio. “In music you have the record producer, whose job it is to put the artist's vision on a medium — in sound. My job here was to take Thomas' vision and make it a reality on paper,” Oestreich said.

It didn't hurt that Oestreich had firsthand experience touring the country with Watershed at the same time Whiskeytown was making the rounds.

“One of the big stories in the book is when Ryan pretty much caused a riot at this place called Mac's Bar in Lansing, [Michigan],” Oestreich said. “We played that place one week later, so we showed up there and everybody was still talking about it: ‘Ryan Adams, that asshole. You should have seen what he did here.' So even though these are Thomas' stories, a lot of the venues where the action takes place, I've been to and Watershed has played, so that helped fill in a few of the details.”

Some of that touring experience also made Adams' tendency to self-destruct hard to watch.

“One thing I had to consciously put aside was, our band got signed around the same time as Whiskeytown, but it was a little frustrating to me when the music industry machine was trying to help them by setting up interviews and publicity, and the band was sabotaging the help. I was thinking, ‘We didn't get any of that!'” Oestreich said. “But even as a guy who wished he had the same major label attention that Whiskeytown did, I'll be the first to admit that doing all of the right things, showing up on time, answering the phone — none of that rocks. Getting all wasted and phoning in the show just for laughs and fun? Or what Ryan does in Aspen, [Colorado], hitting one big E chord and hitting your stomp-box delay pedal and having that chord go on for 20 minutes while Kevin Costner watches slack-jawed? That rocks.”

Plus, if Adams had done everything by the book, there would be no rock mythology handed down by tour managers and bar owners. Waiting to Derail wouldn't exist. “If Ryan was the guy who could show up on time, he probably wouldn't be the guy who wrote those great songs,” Oestreich said. “Even if the songs on Strangers Almanac were exactly the same — and I think that is a brilliant record — and if that tour was just completely safe and everything went according to plan, maybe Whiskeytown would still be together and they'd be as big as Train. But people wouldn't be talking about them in the same way.”