The song features San Francisco 49ers players Joe Montana, Ronnie Lott, Dwight Clark, and Riki Ellison singing backup vocals.

[2] He referenced the book Bobos in Paradise in describing the song's inspiration, explaining that "Hip to Be Square" was about the "phenomenon where people from the '60s started to drop back in, cut their hair, work out, that kind of crap, but they kept their bohemian tastes.

Lewis later modified the lyrics to be in the first person as he believed it would enhance the joke, but stated this had unintentionally led to the interpretation of the song as an "anthem for square people".

The song was then featured in the film adaptation during a scene in which Bateman (played by Christian Bale) gives an abridged version of his critique from the novel to his coworker Paul Allen (Jared Leto) just before attacking him with an axe: "In '87, [sic] Huey released this ...

In addition to the title being a direct reference, the song and video featured an interpolation of the main melody from "Hip to Be Square" during a skit which parodies Bateman's critique of the band.