The group was initially formed as a casual collaboration between Freed, Govrik, and Gorman. The three had met together to jam on multiple occasions, constantly cycling a fourth musician. Trigger Hippy made its live debut on February 2, 2009, at the Cox Capitol Theatre in Macon, Georgia with Herring filling out the lineup. Due to Herring’s tour commitment to Widespread Panic, the group recruited Greene and Osborne. The current lineup toured the south of the US in the summer of 2011, playing shows in Atlanta, Birmingham, Nashville, Memphis, and Chattanooga; performing both original and cover material.

After playing shows throughout California, the group spent January 2012 at Mission Bells Recording Studio in San Francisco recording tracks for their upcoming debut album. In March 2012 it was announced that, after finishing these recordings, Freed had left the band. In his place, the band brought in Will Kimbrough, who was then replaced in August 2012 by Bukovac.