German cultural theorists Walter Benjamin and Theodore Adorno were outspoken in lamenting the industrially-churned sameness produced by the culture industry, yet both men also saw the power of truly authentic work to deliver moments of introspection (or, as is often the case in modern art, to highlight the absence of them). The visual technologies of the twentieth century have the power to lull us into submission, but also to politically energize mass audiences through propagating absurdity, imperfection, and confrontation. According to Benjamin’s theories, film may even have the power to form a window into the unconscious. The philosophy sustained and elucidated by these two men has had a profound influence on modern American comedy, particularly in the work of comedians Tim Heidecker and Eric Wareheim. Throughout their oeuvre of surreal comedy sketches, Tim and Eric take up the complex themes of alienation, greed, inadequacy, and a Freudian obsession with paternity (and by extension patriarchy), and feed them roughly through the meat grinder of lowbrow comedy. The result embraces the derivative, the faulty, and the profane, creating authenticity by pointing out the hopelessness in trying to achieve it. In the process, their comedy expands our sensibilities and sensory vocabularies, challenges our relationships to reality, and redefines the scope of artistic expression.