Faithless Street serves as an interesting document in the history of alt-country upstarts Whiskeytown, showing 20-year-old bandleader and chief songwriter Ryan Adams' headfirst leap from member of a high-school punk band into an emotionally charged, alcohol-fueled, traditional-minded country singer. The majority of the album was recorded in the summer of 1995 near Whiskeytown's hometown of Raleigh by Chris Stamey (of the dB's) and overflows with beer bottle, front porch, sun-drenched country anguish. Of the recording, Adams would later recall: "All I remember is what we had to drink and Skillet and Ray Duffy's preoccupation with fireworks... the Roman candles and black cats sounded a lot like I'd hope we'd one day sound -- pretty little things all set on fire waiting to get destroyed." Looking back on this statement, the band's history of lineup changes and well-documented onstage fights seems to fit intoAdams' five-year plan perfectly. The music itself is often sparse and gritty, brutally honest, and quite beautiful, especially in the introspective "If He Can't Have You," "Desperate Ain't Lonely," and the achingly gorgeous "Excuse Me While I Break My Own Heart Tonight." For all of the attention surrounding Adams' songwriting and Gram Parsons-like self-destructive bluster, one of the album's highlights comes from violinist and vocalist Caitlin Cary's "Matrimony," sung with a fierce independence that is a far cry from Tammy Wynette's "Stand By Your Man," although with a similar heartfelt enthusiasm. Regarding his songwriting in the Faithless Street era, the lead singer later confided: "In retrospect, I knew that was the last optimism I was gonna have for a long time," which sounds implausible regarding most of the album's subject matter, but later proved to be true. Overall, the album (re-released in 1998 by Outpost Recordings with several bonus tracks) stands as a terrific recording on its own, and also foreshadows many of the forthcoming troubles and achievements in the arc of the band's life span.