"All the recordings I had done in the past hadn't really represented me in the way that I wanted to be represented." Musicians Pete Maloney (Dishwalla, Tonic), keyboard player Will Hollis (Eagles), and steel guitar player Eric Heywood (Ray LaMontagne) were brought in to help create an honest record based around Andrew's rhythmic guitar and expressive, soulful vocals.

With "Fifty Miles to Chicago", Ripp aimed to create an organic album reminiscent of those made in the 70's and by artists like Otis Redding, Bob Dylan, and Hank Williams. From the electricity of the organ-driven groove of "Get Your Smile On", to the indie-rock drunken bar sing-along of "The Privileged Life", and the heart-wrenching rock ballad of "Dresden Wine", he does just that.