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This article considers Canadian comedian Debra DiGiovanni’s self-deprecatory humour as a performative strategy. In keeping with a performance tradition of self-deprecation as established by women like Phyllis Diller and Joan Rivers, DiGiovanni offers ‘failure’ as a comic strategy. Her comedy is heavily reliant upon the framing of her lack in relationships, in self-control and in body image (in relation to normative gender standards and expectations). At the same time, however, DiGiovanni also engages critically with gendered expectations of heteronormative desirability, lampooning thin women, superficial men and celebrity culture. Although her comedy is generally characterized by self-deprecation, her humour also leaves space for an ambivalent politics of gender.