Dierks Bentley followed up his debut album with the successful sophomore album Modern Day Drifter in 2005. The album featured hits "Lot of Leavin' Left to Do" (#3), "Come a Little Closer" (#1), and "Settle for a Slowdown" (#1). While the album was successful from a singles and commercial standpoint, Aaron and Emily struggle with how to rate the rest of the album as they have a preference for his more recent music.