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Waiting to Derail: Ryan Adams and Whiskeytown, Alt-Country's Brilliant Wreck

Name: Waiting to Derail: Ryan Adams and Whiskeytown, Alt-Country's Brilliant Wreck
Brand: Skyhorse Publishing
SKU: 9781510786417
Price: 19.99 USD
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Contributors:

Thomas O'Keefe, Joe Oestreich

Publisher:

Skyhorse Publishing

Genre:

Rock

Binding:

Paperback

Book Category:

Music, Biography & Autobiography

Book Subcategory:

Genres & Styles, Entertainment & Performing Arts, Music

Book Topic:

Rock

Edition Description:

Reissue Edition

Shipping & Return +

The product is eligible for a complimentary return within 30 days from the date of purchase. Furthermore, individual items are shipped within 24 hours of receiving the order.

Rating and Reviews +

Specifications +

Release Date:

12/9/2025

ISBN 13:

9781510786417

Weight:

0.71 lbs

Size:

Pages:

280

Mint Condition +

product description

Description

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.

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 classic: Strangers Almanac. That's when tour manager Thomas O'Keefe met the young musician.

For the next three years, Thomas was at Ryan's side: 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 breakup: Ryan, fiddle player Caitlin Cary, and Thomas O'Keefe.

About the Author
Thomas O'Keefe was the tour manager for Ryan Adams and Whiskeytown from 1997 until their breakup in 2000; he is currently the tour manager for Weezer. His twenty-plus year career in the music business includes twelve years with Grammy winners Train and shorter stints with acts as diverse as D Generation, Sia, Third Eye Blind, and Mandy Moore. He was also the bass player for North Carolina punk band ANTiSEEN, recording thirty-eight releases and playing concerts across the United States and Europe. O'Keefe lives in Nashville, Tennessee.
Joe Oestreich is the author of three books of creative nonfiction: Partisans, Lines of Scrimmage (cowritten with Scott Pleasant), and Hitless Wonder. His work has appeared in Esquire, Creative Nonfiction, River Teeth, Fourth Genre, The Normal School, and many other magazines and journals. Four of his pieces have been cited as notable essays in the Best American series, and he's received special mention twice in the Pushcart Prize anthology. He teaches creative writing at Coastal Carolina University. Oestreich lives in Myrtle Beach, South Carolina.