This chapter finds a paradigm for thinking about embarrassment in the music of pop artist Tori Amos because of the myriad ways in which embarrassed thinking and feeling haunts the production and reception of her work. Distinguishing embarrassment from shame and emphasizing the cringe rather than the blush as a synecdochic sign for the ways in which embarrassment appears in and moves through contemporary scenes of cultural activity, the chapter also locates the value of a specifically critical form of embarrassment in its capacious, reflexive refusal to segregate intellective endeavor from its supposed obverses or enemies (earnest sentiment, intransigent stupidity, fandom attachments). Perhaps surprising, Amos does not just thematize embarrassment in her compositions and performances or incite embarrassment in some of her listeners but also models the form of critical embarrassment that this chapter anatomizes and affirms, as she undertakes fraught negotiations required to survive and thrive in the contemporary music industry.