It's time to look at what is not so funny about funny business. While comedy traditionally embodies a spirit of renewal and humility, a new, disheartened form of comedy has begun to thrive in today's media-saturated and politically charged landscape. When Comedy Goes Wrong examines how, in the late twentieth and early twenty-first centuries, disillusioned comedy has found a platform amid polarizing cultural politics. From the calculated follies on talk radio programs like the Rush Limbaugh Show to the anticomedy of the movie Joker and "cancel culture," to the carnivalesque antics of participants in the Capitol insurrection, and development of so-called Alt-Right comedy, the transgressions and improprieties and ego trips endemic to comic freedom have mounted up to an entire discourse of culture and politics. Christopher J. Gilbert challenges the prevailing belief in humor's inherent social and political efficacy by analyzing radio personalities, meme culture, films, political commentary and revolt, and even the language of ordinary individuals and everyday speech. By considering what happens when humor becomes humorless, When Comedy Goes Wrong paints a nuanced portrait of humor's role in today's tumultuous cultural landscape. It challenges assumptions about comedy's unequivocal benefits to democratic praxis, going beyond partisanship to explore the uglier parts of American culture.