The work of singer-songwriter Tom Waits belongs musically and lyrically in the canon of culturally significant late twentieth-century popular music. Working against the grain, drawing on blues, jazz, the “great American songbook,” Jack Kerouac’s prose, outmoded slang, industrial noise, and overheard conversations, Waits has produced a body of work – hundreds of songs and performances – that, to most Americans, would seem grating, nightmarish, and hardly representative of national experience. The critic Greil Marcus famously characterized much of Bob Dylan’s output as coming from the depths of a mythical “old, weird America” of repressed roots. This chapter maintains that Waits’s work portrays an uncanny American scene older and weirder than anything Dylan has produced. Through stories and parables in song; through creative re-use of obsolete words and phrases; by constructing a harsh sound composed of American folk traditions, revival exhortations, blues hollers, carnival riffs, and found bits of junkyard percussion – Waits has created an anti-America in hopes of redeeming cultural fragments lost or passed over during urbanization, consumerization, and cultural homogenization. His uncanny, old, weirder America is alienated from national imaginaries and yet oddly patriotic, though never political or reformist.