In 1998, James Dewees recorded his first solo album under the pseudonym Reggie and the Full Effect. While Dewees wrote the songs himself, he asked Matt Pryor and Rob Pope to help record some of the instrumentals. The resulting album, Greatest Hits 1984-1987 leaned heavily on the use of synthesizer keyboards for its sound. Their work together on the Reggie and the Full Effect album led Pryor to invite Dewees to collaborate with The Get Up Kids on "Red Letter Day", a five-track EP produced by Ed Rose to fulfill their two-record deal with Doghouse. The cleaner, more focused sound of the EP provided the chance to experiment with the inclusion of keyboards and acts as a sonic bridge between the raw sound of "Four Minute Mile" and the more dynamic, produced style of their next studio album.