This paper explores two adaptations by rock musician Lou Reed of the Velvet Underground and Metal Machine Music fame. Reed has always been a complicated and controversial figure, but two of his albums—The Raven (2003), a collaborative theater piece; and Lulu (2011), a collaboration with heavy metal band Metallica—have inspired confusion and vitriol among both fans and critics. However, both adaptations, rich in intertextual references, at once show Reed to be what music historian Simon Reynolds calls a portal figure—offering a map of references to other texts for fans, indicating his own indebtedness to prior art—and to also be an uncompromisingly unique and original artist. This thesis analyzes both The Raven and Lulu and their adaptive connections to their source texts (the collected works of Edgar Allan Poe and the Lulu plays by German modernist Frank Wedekind) through the lens of adaptation theory. Although both albums, especially Lulu, were vilified by fans and critics alike, an exploration of both texts and their sources reveals a more complicated reading of the albums, as well as shedding light on adaptation theory. Reed's adaptations, in particular, offer compelling new insights into notions of fidelity—between an adaptation and its source, as well as between Reed and his career—and also promote alternative forms of listening pleasure, which challenge cultural and music industry boundaries regarding contemporary music. Lou Reed and his adaptive practice occupy a crucial position in the adaptive process, in both rock and heavy metal music.