"The Headless Children" showcases a new level of maturity from the band compared to their previous three albums, which had stereotypically lewd "rock and roll" lyrics. Politics and social issues are now a theme throughout the album. The cover art, based on "Gateway to Stalingrad", a cartoon by Daniel R. Fitzpatrick, depicts a string of historical figures including Joseph Stalin, Adolf Hitler, Heinrich Himmler, Benito Mussolini, Charles Manson, Jim Jones, Idi Amin, Pol Pot, Al Capone and the Ku Klux Klan, with an image of Jack Ruby shooting Lee Harvey Oswald shown prominently in the foreground. Later editions of the album have replaced, among others, Ayatollah Khomeini with additional KKK members.