Monroe was born in Clearwater, Florida. He grew up in California, Connecticut, Kansas, North Carolina, and England. There was no history of music in his family, as most of his family members were lawyers. He started off playing the drums at age nine but then switched over to singing.
His music career started with hard rock, and he was the lead singer for a hard rock bar band before learning guitar and songwriting, which sent him off in a mellower solo direction. Monroe started working the coffeehouse circuits, but then he formed his own band and developed a touring schedule of over 100 dates a year. He established his own record label, Divorce Records, in 1996. He would later release all his four albums on the imprint. In 1999, when he was based in Los Angeles, Monroe recorded his album Shame at CAM studios in Bulverde, Texas.
He covered the song "Midnight Rider" in 2005 as the lead single from his album Against the Grain. Calling him a "musician's musician", Billboard commented that his "warm, supple" voice brought "an edgy energy" to the song. In 2007, Monroe moved to Nashville. His "Crazy Not To" single, released in the summer of 2012, reached top-40 radio and chart status.

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