This volume is the first book-length study of 21st-century English-language cringe humor on screen and in digital media. The book includes quantitative and qualitative analyses of verbal and multimodal cringe humor by international linguists interested in its conditions of emergence and success. It examines the sociocultural variables involved in its reception and sheds new light on audience reactions—from alignment to disaffiliation and resistance to empathy. This book reveals that, while not unanimously championed, cringe humor thrives in the 21st century, drawing on its inherent ambivalence and leveraging the affordances of new media to navigate the post-politically correct ethical complexities of laughing at embarrassing behavior. With its cross-disciplinary, pragmatically grounded approach, this book will interest scholars and students in Linguistics, Media and Cultural Studies, and Psychology.