In 1996, Pearson formed the short-lived, but critically acclaimed band Lift to Experience, who released one double album, The Texas-Jerusalem Crossroads on Bella Union in 2001, before splitting up soon after.

After Lift to Experience disbanded, Pearson retreated to Limestone County, Texas, doing odd jobs to get by while he continued playing and writing music.

[2][3] His only studio recording during this time is a cover of Hank Williams' song "I'm So Lonesome I Could Cry", which was released on 7-inch split single also featuring Dirty Three, and appearance on West Country Night - Session One compilation album.

He also provided guitar and backing vocals on two songs, "Seal Jubilee" and "Trophy", on Bat for Lashes' 2006 Mercury Music Prize-nominated album Fur and Gold.

[30] Pearson's song "Country Dumb" appears in the 2012 Martin McDonagh-directed motion picture Seven Psychopaths[31] and "Woman, When I've Raised Hell" in the 2013 Ridley Scott thriller film written by Cormac McCarthy, The Counselor.