While conventional wisdom has it that humor embodies a spirit of renewal and humility, a dispirited form of comedy thrives in a media-saturated and politically charged environment. When Comedy Goes Wrong examines how, beginning in the late-twentieth and carrying into the early twenty-first century, a certain comic dispirit found various platforms for disheartening cultural politics. From the calculated follies on talk radio programs like the Rush Limbaugh Show through the charades of "cancel culture" and ultimately to so-called Alt-Right comedy, the transgressions, improprieties, and ego trips endemic to a newfangled comic freedom produced entirely unfunny ways of being. To understand these unfunny ways, Christopher J. Gilbert challenges the prevailing belief in humor's goodness, analyzing radio personalities, meme culture, films, civil unrest, and even the language of ordinary individuals and everyday speech, all to demonstrate what happens when humor becomes humorless. As such, Gilbert imagines a nuanced sense of humor for a tumultuous world. Ultimately, When Comedy Goes Wrong transcends partisanship to explore the uglier parts of American culture, imagining the stakes of doing comedy—and being comical—as a means of survival.