Living Inside My Head follows the musical and spiritual journey of Paul Gilchrist, a young rock musician, after he founds a band with the charismatic Jeffrey Hart as lead singer and frontman. After college, Paul, an aspiring singer/songwriter, moves back to Kingston, Ontario, his hometown and meets Rock Desmarteaux and Jeffrey Hart. All three love music—Rock hosts a radio show and Jeffrey is an accomplished singer and guitarist. When Paul starts a band with Jeffrey called The Dregs, Rock appoints himself as their “Quality Evangelist.” After moving to Toronto to be managed by a madcap entrepreneur called Crazy Guy, success eludes them and they almost break up. Everything changes when they meet Patrick, the founder of independent label, Lipstick Records.