This thesis explores genre and gender in Joss Whedon's web miniseries, Dr. Horrible's Sing-Along Blog. The plot of the web miniseries follows Billy, whose alter ego is the wannabe villain, Dr. Horrible. He spends the majority of the miniseries attempting to commit villainous crimes that will, he hopes, get him placed into the Evil League of Evil, falling for the woman he has a crush on, Penny, and avoiding his arch nemesis, the hero Captain Hammer. The web miniseries is representative of elements of Joss Whedon's auteur signature, also holding implications for the director's self-declared "feminist agenda." This thesis utilizes genre theory and conversations about the musical genre to analyze how Dr. Horrible revises the musical genre. Furthermore, the differences between the musical and non-musical sequences serve to illustrate the duality of Billy's character. The analysis also delves into the tensions between civilized, primitive, hysterical and hegemonic masculinities, as Billy/Dr. Horrible ultimately struggles with all of these forms. Although Billy/Dr. Horrible's struggle with masculinity is central to the narrative of the web miniseries, the depiction of femininity and Penny's character is also explored. Finally, after exploring the role of Whedon's auteur signature, and genre and gender in the web miniseries, the thesis explores the relation between Dr. Horrible and convergence culture, and the role of the web miniseries in the evolution of the Internet as a mode of distribution.