We're accustomed to seeing humour as a diversion from the serious side of life, but humour also permeates some of the most troubling political developments in recent years. From the resurgence of white nationalism to the erosion of democratic norms, jokes force-feed us objectionable ideologies while we gasp and splutter at all the side-splitting shenanigans. This book explores the relationship between humour and offensiveness in contemporary society. Drawing on examples from philosophical thinkers and popular culture, it invites readers to consider the dark side of humour. Weaving together cultural analysis, political discussion and philosophical reflection, the book provides an antidote to positive thinking about laughter and a roadmap for navigating different types of offensive humour.