The founding of Whiskeytown saw Adams move to alt-country, describing punk rock as "too hard to sing" in the title track of Whiskeytown's debut album Faithless Street.
Whiskeytown was heavily influenced by the country-rock pioneers, most notably Gram Parsons.
In 2000, Adams left Whiskeytown and released his debut solo album, Heartbreaker, to critical acclaim.
After obtaining his GED, Adams left Jacksonville for Raleigh, shortly followed by Mc Ilwean.
The Patty Duke Syndrome split in 1994 Following the breakup of The Patty Duke Syndrome, Adams went on to found Whiskeytown with Caitlin Cary, Eric "Skillet" Gilmore, Steve Grothmann and Phil Wandscher.
His childhood has been described as "dysfunctional." His father left when he was five and at that time he, his mother and his brother and sister had to move in with his grandparents as they became homeless as a result of the divorce.
Ryan was raised by his mother as a single parent until he was 13 at which time she remarried.
Then later, when I was a teenager, I got really hard into cult fiction: Hubert Selby, Jr., Henry Miller, Jack Kerouac." At the age of 14 Adams began learning to play the electric guitar that his mother and stepfather had bought him, and shortly afterward joined a local band named Blank Label.