This chapter focuses on examples of comedy practitioners engaging in behaviour online which was perceived by audiences to be offensive. The offensive actions or jokes in each case led to criticism online which caused audiences to engage in digital vigilantism directed at the comedy practitioners. In each case the reaction from audiences led to a negative effect on the practitioners’ career, though in some cases audiences also rallied around the practitioner in their defence. The primary issue in these cases is that comedy is inherently subjective, and relies on both the audience understanding the joke, and the practitioner being of appropriate agency to make fun of their target. In online spaces such as Twitter or YouTube it can be harder for audiences to differentiate between an individual, and a comedian playing as a fictional version of themselves, and as such there can be confusion regarding intent and agency. This confusion is exacerbated as some claims of intent occur after the publication of a joke and as such it is unclear if they are genuine, or a response to negative reactions from audiences. This chapter discusses the way that the cultural capital of comedy is changing, the responsibility of the practitioner, and the circumstances in which audiences become digital vigilantes.