Probably the most immediately remarkable aspect of Waits' music is his vocal quality, both in its recognizability and its variety (Montandon 2005). Also significant are the intersections between Waits' music, his life, and theatrical elements (Hoskyns 2009), most clearly reflected in several albums of music composed for the stage. Unlike much of rock music since the 1960s, which claims some form of implicit autobiography as the voice of the singer/ songwriter, Waits' songs are (often overtly) inhabited by fictional personas (see BaileyShea 2014) who speak in distinct voices, figuratively and literally. In this paper, I explore the hypothesis that there are a relatively small number of character archetypes in Waits' music, whose songs are marked by a high degree of intertextuality and common vocal timbre. An empirical approach supplements close analysis of several Waits songs in support of my theory. For the empirical study, 72 participants each categorized 40 randomly-selected Waits songs by vocal timbre out of 147 vocal tracks beginning with Swordfishtrombones. Participants were given 5-second excerpts beginning from the voice's first entrance in each song and told to sort songs into as many as eight categories by vocal timbre. Once sorted, participants provided descriptive labels, and then hierarchically sorted each group until there was only one left. The excerpts were additionally subjected to feature extraction for timbral cues, and texts for each song were analyzed for emotional and topic categories. Analysis of the results suggests ten timbral categories, representing ten character archetypes.