After experimenting with narrative storytelling through shifting genres on Susquehanna in 2007 (Latin Pop, Swing, Ska, Glitter Rock), the band felt the need to put out something straight forward and fun, taking a cue from their 1998 compilation CD.
"Just as our swing fans did before Zoot Suit Riot, fans of our Ska songs have been suggesting that we release all of them together", lead singer Steve Perry explained, "
so they wouldn't have to press the skip button over a western swing song with a lap steel, or a Flamenco track. Now they can just throw a Cherry Poppin Daddies record on without having to explain, and possibly apologize for our eclecticism".
With Skaboy the Daddies plan to reconnect with a Ska audience that is largely aware of the band as merely a swing band. "We toured with many of the iconic ska bands when we were coming up," Perry said,
"the Mighty Mighty Bosstones, Fishbone, Reel Big Fish, The Specials, No Doubt, Madness but at that time we were really touring behind Zoot Suit Riot, so we didn't play a ton of Ska in our sets, now we will."