[5] In 1998, the band released a 7-inch single, "Jukejoint Girl," and in 1999 the album The Two Dollar Pistols with Tift Merritt on Yep Roc Records.

The record landed on the top ten lists for both Time and The New Yorker, and was called the best debut of the year by the Associated Press.

[8] While touring to promote Bramble Rose, Merritt opened for fellow North Carolinian Ryan Adams, who had helped her secure her first management and record contracts.

[9] Her follow-up release, 2004's Tambourine, was produced by George Drakoulias and featured backing by Benmont Tench, Mike Campbell, Neal Casal and Don Heffington.

[citation needed] Merritt has been the opening act for Joan Baez,[20] Kris Kristofferson,[21] and sang "The Star-Spangled Banner" for then-Senator Barack Obama at his last campaign rally.

[27] A review in The New Yorker praised her[27] and The Wall Street Journal included her in a weekend feature on singer-songwriters, describing her as "in the tradition of Joni Mitchell, James Taylor and Leonard Cohen".