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, North Carolina in hopes of expanding its following. However, Adams became eager to do something more melodic that 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. But by the time Whiskeytown had signed to a major label -- the Geffen-distributed imprint Outpost Records -- the band had undergone the first in a series of major personal shakeups, and in the summer of 1997, when Whiskeytown's Outpost debut, Stranger's Almanac, was ready for release, Adams and Wandscher were the only official members of the group left. Cary soon returned, but Wandscher left shortly afterward, and Whiskeytown had a revolving-door lineup for much of the next two years, with the band's live shows become increasingly erratic, as solid performances were often followed by noisy, audience-baiting disasters. Consequently, as strong as Stranger's Almanac was, Whiskeytown never fulfilled the commercial expectations created for them by others. In 1999, the band -- which was down to Adams, Cary, and a handful of session musicians -- recorded its third and final album, Pneumonia, but when Geffen was absorbed in a merger between PolyGram and Universal, Outpost was phased out, and the album was shelved; shortly afterward, Whiskeytown quietly called it quits.

Following Whiskeytown's collapse, Adams wasted no time launching a career apart from the band, and after a few solo acoustic tours, Adams went into a Nashville studio with songwriters Gillian Welch and David Rawlings and cut his first album under his own name, Heartbreaker, which was released by pioneering "insurgent country" label Bloodshot Records in 2000. The album received critical raves, respectable sales, and a high-profile endorsement from Elton John, and Adams was signed by Universal's new Americana imprint, Lost Highway Records. Lost Highway gave Whiskeytown's Pneumonia a belated release in early 2001, and later that same year the label released his second solo set, Gold, which displayed less of a country influence in favor of classic pop and rock styles of the 1970s. In the wake of the September 11 terrorist attacks, the album's opening track, "New York, New York," was embraced by radio as an anthem of resilience (though it actually concerned a busted romance), and Adams once again found himself touted as "the next big thing."

Always a prolific songwriter, in a bit more than a year following Gold's release, Adams had written and recorded enough material for four albums. He opted to whittle the 60 tunes down to a 13-song collection called Demolition, which was released in 2002 as he went into the studio to record his official follow-up to Gold. A year later, Adams' concept album Rock n Roll was released alongside the double-EP collection Love Is Hell. Tours around the globe kept Adams busy into the next year as he maintained momentum writing songs and keeping his ever-changing presence in the music press. In May 2005, Adams released his first of three albums for Lost Highway, the melancholic double-disc Cold Roses. Jacksonville City Nights, a more classic-sounding honky tonk effort, followed in September, and 29 appeared in late December. Always prolific, in the interim period before his next album was released Adams posted a large selection of tracks -- including several hip-hop tunes -- on his website, but fans were greeted with more straightforward material on 2007's Easy Tiger and 2008's Cardinology with the Cardinals.

Adams decided to disband the Cardinals in 2009, precipitating an unusual period of quiet from the prolific singer/songwriter. He slowly returned to active duty in 2010, releasing the heavy metal Orion on vinyl-only in the summer and then issuing III/IV -- a double album recorded with the Cardinals during the Easy Tiger sessions -- in November. For his 13th solo album, 2011's Ashes and Fire, the singer/songwriter recruited Norah Jones and Tom Petty & the Heartbreakers' keyboard player Benmont Tench, as well as legendary producer Glyn Johns, who helmed the Who classic Who’s Next.