Right away, this sounds like a country version of Beck to me and I found out by listening to it as such that country Beck is a genre that I like. Throughout the songs though, this does take some changes in the sense that it at least elaborates upon that initial thought into something so much more.
Musically, hints of Forgive Durden come out. Devo can come out vocally and then there is also some funk on a song about Chicago. With so many people singing about Chicago I always wonder whether or not it is a real place, but google searches always seem to prove that it is not.