The music on "Dare to Be Stupid" is built around parodies and pastiches of pop and rock music of the mid-1980s, featuring reimaginings of Madonna, Cyndi Lauper, Huey Lewis and the News, and the Kinks. The album also features many "style parodies", or musical imitations that come close to, but do not copy, existing artists. These style parodies include imitations of Devo and Elvis Presley, as well as imitations of various musical genres such as doo-wop, sci-fi soundtracks, and music from the 1920s and 1930s.