Ryan Adams was born in Jacksonville, NC, in 1974. While country music was a major part of his family's musical diet when he was young (he's cited Loretta Lynn, George Jones, Merle Haggard, and Johnny Cash as particular favorites), in his early teens Adams developed a taste for punk rock and he began playing electric guitar. At 15, Adams started writing songs, and a year later he formed a band called the Patty Duke Syndrome; Adams once described PDS as "an arty noise punk band," with Hüsker Dü frequently cited as a key influence and reference point.
The Patty Duke Syndrome developed a following in Jacksonville, and when Adams was 19 the band relocated to the larger town of Raleigh, NC, in hopes of expanding their following. However, Adams became eager to do something more melodic which would give him a platform for his country and pop influences. In 1994, Adams left the Patty Duke Syndrome and formed Whiskeytown with guitarist Phil Wandscher and violinist Caitlin Cary. With bassist Steve Grothman and drummer Eric "Skillet" Gilmore completing the lineup, Whiskeytown (the name came from regional slang for getting drunk) released their first album, Faithless Street, on the local Mood Food label. The album won reams of critical praise in the music press, and more than one writer suggested that Whiskeytown could do for the alt-country or No Depression scene what Nirvana had done for grunge.