I am going to examine the appearance of Poe’s themes of insanity, melancholy, and love in the context of dark cabaret music. I wish to present that Poe’s depiction of melancholy, madness, and his love life stay relevant in the 21st century cabaret music, in two chapters. The first chapter focuses on the birth of dark cabaret and songs that are inspired by Poe’s literary pieces, from one-liners that use Poe’s portrayal of madness to present the narrators mental struggles in a contemporary context to a song that covers Poe’s relationship with his wife, Virginia Clemm. The second chapter explores the haunting stage play and concept album Edgar Allan Poe's The Haunted Palace, brought to the audience by the founding fathers of dark cabaret, The Tiger Lillies, focusing on Poe’s insanity and the loss of his love.