Skaboy JFK is a compilation of the ska and ska-influenced songs featured on the Daddies' previous studio albums, spanning from 1994's Rapid City Muscle Car to 2008's Susquehanna, excluding only the band's 1990 debut Ferociously Stoned.

[3][4] On February 22, 2009, Perry confirmed the project on the band's MySpace page, revealing that production would take place in March and the album - under the working title of simply "The Skankin' Hits of the Cherry Poppin' Daddies" - would possibly include as many as 15 songs.

He noted the cover art would revisit touches of the Zoot Suit Riot artwork, explaining "...if they look somewhat similar maybe people will put 2 + 2 together and understand that these were special records we did in order to showcase one style, as opposed to getting a wrong impression of what the band is about generally".

PopMatters called the album "excellent" and "packed with irresistible energy", singling out "Hi and Lo" and "Sockable Face Club" as particular highlights,[6] while Blogcritics shared equal praise, citing it as "[proof] that swing and ska are far from dead".

[8] Metro Spirit summarized the record as "a very catchy, very fun and all around toe-tapping, finger-snapping, head-bobbing good time",[9] and The Renegade Rip also complemented the music's energy, again giving particular praise to "Hi and Lo" and "Sockable Face Club", though claiming that eventually the ska rhythms "became predictable and the melodies ran together".