A singer/songwriter whose music combines equal portions of passion, heart, and swagger, Boston native Jake Brennan first made a name for himself as the lead singer with the punk band Cast Iron Hike. Joining the band in 1993 when he was 19 years old, Brennan went on to cut an album and an EP with Cast Iron Hike, but he eventually grew tired of the rigid musical boundaries of the band and developed a taste for country, blues, and roots sounds, some through the influence of his father, Dennis Brennan, a fellow musician with a loyal Boston following.