Cain left Iowa City for the town of Maynard, Iowa, in July 2007. He released his debut, Black Eye, in October 2007, on his own City Rain Records imprint. The album was comprised entirely of autobiographical folk songs, featuring the singer-songwriter on acoustic guitar, piano, and harmonica, as well as production and engineering duties.
Quick to follow was Cain’s sophomore set, Highway 187 Revisited, in March 2008. Recorded in two separate week-long sessions over the course of a brutal Iowa winter, the album again featured Cain on all instruments, including guitar, bass, drums, and harmonica. The 14-song LP was largely made up of electrified alt-country tunes in the vein of Ryan Adams and Whiskeytown.
Cain released his final, self-titled album under the “Matthew Cain” moniker in November 2008. He has since moved on to form the rock band Fitzgerald; they have released one album, 2009’s Nothing Left But The Leaving, and are currently recording their sophomore set, Modern Love.