I argue that the overt subjugation in the system of American slavery and its subsequent effects offer a case study for an existentialist analysis of freedom, oppression and humor. Concentrating on the writings and experiences of Frederick Douglass and the existentialists Simone De Beauvoir and Lewis Gordon, I investigate how the concepts of “spirit of seriousness”, “mystification”, and an existentialist reading of “double consciousness” for example, can elucidate the forms of explicit and concealed oppression. I then make the case that subversive humor is an effective means to bring to consciousness the inconsistencies and incongruities of the serious oppressors. I also illustrate how humor can act as a bulwark against the rise and persistence of oppression by (non-violently) attacking the absolutist stance on human nature maintained through the use of dominating and “authoritative” language and action.