After one year of college, he decided to drop out and begin traveling, an experiences that would later deeply influence his songwriting.
Weaver's debut album, El Camino Blues, was released in 1999 and featured Greg Brown, with input from Tony Glover.
Over the years, Weaver has toured with numerous artists including The Waifs and Kristin Hersh.
Weaver's 2010 album, Mirepoix and Smoke, was inspired by his time working in a Minneapolis restaurant after taking a break from recording and touring in 2009.
His short story, "Humanesque," was featured in the 2009 anthology Amplified: Fiction from Leading Alt-Country, Indie Rock, Blues and Folk Musicians, and his poem "Devastations" won the 2009 What Light Grand Jury Prize.