This chapter takes the popularity of J. D. Vance’s Hillbilly Elegy (2016) as an opportunity to witness the power of tropes that politically and culturally juxtapose urban and regional concerns, and to explore critical regionalist alternatives to rhetorics of disconnection. It examines assumptions about regions that underly Vance’s “hillbilly” and the ethno-national difference between urban and regional spaces. Vance’s Appalachia had unfortunate resonance in a turbulent political season, spawning a subgenre “Trump Country” essays. A critical regionalist uses these characterizations as an occasion to affirm alternative versions of region. Moving quickly and collaboratively, a network of artists and scholars responded in diverse works, landmarked by What You Are Getting Wrong about Appalachia (2018), the documentary film hillbilly (2018), and the multigenre collection Appalachian Reckoning: A Region Responds to Hillbilly Elegy (2019). These works and the conversations they generated across media create a multivocal portrait of a place that must be understood from a perspective that does not see city and region as antithetical but maps interconnections of urban and rural spaces.