The songs on the compilation cover a broad range of styles of ska music, including traditional Jamaican-influenced ska, reggae, third wave ska and ska punk.
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In mid-2009, the Daddies signed to independent label Rock Ridge Music, home of former Mojo labelmates Reel Big Fish (who, coincidentally, would also release a ska compilation of re-recorded tracks due to an identical conflict with Jive Records), for the national release and distribution of both Skaboy JFK and a re-issue of Susquehanna.
Both songs were later re-recorded, "Hi & Lo" for the Daddies' 2008 album Susquehanna and "2:29" for the 2009 compilation Skaboy JFK, which also included the re-recording of "Hi & Lo".