In his spare time, however, he began writing material of his own, citing the music of Nick Drake and Pete Seeger and the writings of Flannery O'Connor as key influences. Some of Tillman's demos found their way to Damien Jurado, who invited Tillman to join his band for a tour. Tillman played solo sets during several dates on the tour and began distributing CD-R copies of an early collection of tunes called I Will Return. During the tour, he also struck up a friendship with Eric Fisher, who produced another CD-R album, Long May You Run, J. Tillman. Both Tillman and Jurado later signed on for a U.S. tour with Richard Buckner, where Tillman once again found a ready audience for home-burned copies of his disc.

In 2006, the independent Fargo Records label released Tillman's first properly distributed solo album, Minor Works, and Keep Records reissued I Will Return and Long May You Run as a two-disc set the same year. In 2007, Yer Bird Records released Tillman's fourth, more elaborately arranged album, Cancer and Delirium. Although his solo work continued to garner critical acclaim, Tillman briefly shifted focus in 2008 by joining Fleet Foxes. The group toured heavily in support of its debut album; meanwhile, Tillman continued working on his own material, releasing Vacilando Territory Blues in 2008 and Year in the Kingdom in 2009. In 2011, Tillman left Fleet Foxes to concentrate on his many solo projects, adopting the pseudonym Father John Misty for 2012's Fear Fun, a twelve track collection of new material that infused the harmony-laden hymns of his former band with a patina of Gram Parsons and Harry Nilsson-informed, Laurel Canyon-inspired, neo-psychedelia. ~ Mark Deming