Tim, you’ve nailed it, absolutely. Twentieth century America’s always been mythic for Waits, and when I showed up his songs just slotted me right into their reality picture. You’re right about the critical gaze, too — more about that tomorrow. (And about Lovecraft’s critical gaze, too, though in his case I think we’re looking at some serious ophthalmological problems, maybe fungal keratitis.)

I think the critical thing with Waits is that he is not of the time and spaces he sings about. He tells stories like they are fantasies, whether they be of the Beat, long drunk night of trucks passing cars in the howling night, or the abandoned Southern barns where slaves were once slaughtered. He romanticizes these places, people, and events, but he also stands outside of them, often with a critical gaze. This self consciousness makes me think he is either 1) of that 21st century world and he is looking back, creating a mythological 20th century or 2) he is indeed part of the 20th century, but is engaged with those parts that culturally most Americans have chosen to ignore or were never aware of in the first place. He shows us just how weird that time was, and how strange our time continues to be (if you have not heard it, his latest album of new material, Real Gone, exemplifies this… its all trash-fantastic, carnies and broken trains, rain and war and nihilism, love and murder, ghosts and wine glasses).
In a lot of ways, his approach is similar to Bob Dylan’s. He uses the detritus of the past two centuries to cobble together narratives and sounds that the underbelly of the present.