The paper considers a wider scope of the artistic practice of one of America’s best-known contemporary writers of poetry and prose; the prolific underground writer Charles Bukowski (1920-1994). He is taken as a representative example of an individual’s resistance to the established society – a stance that is continuous throughout his writings. Bukowski’s works replicates a ‘post-modern Steppenwolf’. He is an outsider, beyond society’s norms. To explore living beyond society is to gain a greater understanding of the self. Yet, the truly free life beyond society is non-existent, since it would be ‘social death’. One lives inside society, so one has to embrace it in one way or another. Bukowski was socially disgusted. But beyond society and its relations, one does not exist. Bukowski wrote himself away from this position. His texts are a protest against that it has to be this way; with his writings he battled the social death.