This chapter investigates cringe humor in late-night television talk shows. Unlike genres relying on fiction, talk shows include interviews with real people, mostly enjoying the status of celebrities. Cringe-humorous situations in such interactions appear both in personal anecdotes touching upon taboo subjects and in dialogues, in which the norm stipulating respect and appreciation to others may be violated. Drawing on the characterization of the talk show as a mixed type of discourse, combining the characteristics of institutionalized interaction with spontaneous dialogue, and on the assumption that transgressions of social norms must be perceived as benign in order to be amusing, I analyze manually selected examples from late-night talk shows, demonstrating that the design of the participation roles and the mixed nature of the talk show discourse are conducive to creating humorous cringe.