Bo Burnham’s Inside, promoted as a musical comedy special by its platform Netflix, released in June 2021 to almost unquestioning praise, and has now won 3 Emmys. The work is an evocative retrospective of Burnham’s fictionalized experience during the Covid-19 quarantine. Written, performed, filmed, and edited by Burnham himself, the piece reflects his career as a musical comedy performance artist, and also provides an intimate look into his struggles with mental health, internet culture, and artistic ego. Of particular appeal in this piece is the complex pairing of comedy with pathos. Its songs have become ironic backgrounds to TikTok videos and popular sea shanty renditions. Critics remark: ‘What he’s describing is the near-universal feeling of despair in 2020. And that feels good’ (Herman 2021); ‘A tricky work that for all its boundary-crossing remains in the end a comedy in the spirit of neurotic, self-loathing stand-up’ (Zinoman 2021); ‘A claustrophobic masterclass in comedy and introspection, Inside is a beautifully bleak, hilariously hopeful special’ (Rotten Tomatoes). It is this complexity which I seek to investigate. I assert that Bo Burnham’s Inside achieves its poignancy not through its comedic stylings, but through its implementation of a traditional Aristotelian tragic structure. This paper will discuss the ways in which Burnham follows the tragic structure and the monomyth while engaging with, and subverting, benign violation theory to provide a postmodern catharsis in its audience that feels like comedy, but ultimately provides a shared expression of, and outlet for, the audience’s grief.