Ross Grady’s name comes up a couple of times throughout “Losering,” which is fitting. He’s been an important presence in Triangle music for more than two decades, as a writer, deejay, obsessive chronicler, devoted fan, gadfly and all-around bon vivant. Ross was friends with various members of Whiskeytown as the group was forming in 1994 and he’d known of Ryan before that, when Ryan would call up trying to talk himself onto the WKNC local-music radio show Ross did. Ross discussed that when I interviewed him for the book in 2011:
I remember I was living on Cutler in Boylan Heights in about 1993, circa Patty Duke Syndrome. My phone was ringing, I answered and it was this Ryan Adams guy who wanted to tell me things about what he was doing. There was this adorable assumption that I’d give a shit, even though I’m pretty sure I had no idea at the time who he was. You know, jerks call all the time telling you crap you don’t want to hear about their awesome band. But at some level, Ryan was qualitatively different. It was funny as opposed to disturbing, which calls like that usually are. What was sort of endearing about Ryan was he had absolutely zero self-consciousness at all about it. He just had this assumption that you needed to know what he was doing, but not in an obnoxious way like 50 other people you could name. I can’t put my finger on why. I almost feel like it was because I’d never heard of anything he was talking about. Usually when people call they’ve already mailed their stupid tape, I’ve seen their stickers in every bathroom around town and they have a reputation as being irritatingly self-promotional. Ryan was the same, but somehow I’d never heard of him.
Ross wrote the earliest story on Whiskeytown that I could find — January 1995 in The Independent, an alternative country-themed piece about Whiskeytown (then “Whiskey Town”) and Pine State in which 20-year-old Ryan declared, “I don’t have time to be unclear — I’m going to die someday.” A bit more than three years after that, Ross had an entertaining interaction with Ryan at a show in the spring of 1998. It was a well-oiled conversation that concluded with Ryan drawing up a “contract” promising the following:
I hearby give Ross Fucking Grady the rights to anything I did that sucked.
You can read more about this in Chapter 10. The document in question is archived for posterity online here — or you can check it out below. In October 2001, not long after the big Guitatown dustup, Ross posted a picture of this to the online newsgroup alt.music.chapel-hill under the heading “The ‘Suck’ Trial.” That triggered several days of lively commentary, including Ross’ own observation that he “should start seeing checks from Gold any fucking day now.”