Lead singer Ron Hawkins, guitarist Stephen Stanley and drummer David Alexander were previously in the band Popular Front, but when they formed The Lowest of the Low, Hawkins, who wrote all but one of the songs on the record, made a change in his songwriting for the material that would ultimately become "Shakespeare My Butt."

While he had previously written material that was "about big global issues" and "places sort of far from ourselves and people that were not in our immediate circle," Hawkins began writing songs that were "much more personal, much more close to me... much more about my surroundings."

Hawkins explained "The whole thing with Shakespeare My Butt was... a whole bunch of songs that dealt with my neighbourhood and my local bars and characters I would run into.

When they had moved 4000 copies of the self-released album they struck a distribution deal with Page Publications (run by former Barenaked Ladies vocalist Steven Page's father Victor) and were soon moving a lot of copies at Toronto's HMV Superstore thanks, in part, to heavy radio play when CFNY began to champion the band.

The album was remastered and re-released in 2010 on Pheromone Recordings, with an accompanying short film DVD, LowRoads, produced by the band's drummer, David Alexander.

"[9] British author John Donoghue's 2004 book Shakespeare My Butt!, a humorous travel memoir of quirky destinations in Great Britain, also took its name from the album; Donoghue acknowledges the band's influence in the book, and the cover features a blindfolded image of William Shakespeare in homage to the blindfolded band photo on the album cover.

Two songs from the album ("Letter from Bilbao", "For the Hand of Magdalena") are featured in virtual museum dedicated to the Spanish Civil War.