Following the huge success of the band's 1997 swing single "Zoot Suit Riot", Perry sought to write a song which would introduce a truer perspective of the Daddies' sound to a wider audience and help bridge the gap between their swing-oriented fanbase and non-swing music.

[7][8] "Diamond Light Boogie" worked as a musical and lyrical homage to the glam era of the early 1970s, written to fuse the guitar riff-driven melodies of bands such as T. Rex with the rhythmic backbeat and upbeat horn section common of jump blues and swing.

[citation needed] Perry has described Soul Caddy as a loose concept album reflecting his own temporary experience with fame, drawing upon feelings of social alienation, disillusionment and dissatisfaction with the cultural zeitgeist.

[8] Perry described Soul Caddy as a "bittersweet" record about "being alienated and hoping to connect", noting the central themes of the albums as being about loneliness and the search for meaning in a "technically sophisticated yet soulless society".

[4] Openly discontent with the media's persistent typecasting of the Daddies as a generic "retro swing band" at the expense of their dominant ska and punk influences, Perry started writing more diverse musical textures into the album rather than merely return to an overtly swing-oriented sound.

[20] MTV.com offered perhaps the most overwhelmingly negative review, saying that Soul Caddy's "cheesy, super-compressed studio shine" had drained the album of its energy, leaving the "confusing" mix of genres feeling "washed-out [and] a bit depressing and Weird Al-like", summarizing the Daddies as "a band that's trying to show off their record collection, rather than their creativity".

[23] Bogged down by poor reviews, neither Soul Caddy nor "Diamond Light Boogie" achieved any commercial or chart success upon release, casting an unshakeable pall over the Daddies' subsequent US tour in promotion of the album.

In December 2000, the Daddies mutually agreed upon taking an indefinite hiatus from performing, citing both Soul Caddy's commercial underperformance and the band's personal exhaustion from nearly non-stop touring since the release of Zoot Suit Riot as reason.

[15][24] The Daddies would eventually reform in February 2002 to sporadically play one-off local shows and festival appearances for the next several years before returning to touring and recording with their self-produced and independently released album Susquehanna in early 2008.