Our chapter elaborates on the entrance of Playboy into Israeli media in the beginning of the millennium. It contends that this development paved the way for pervasive consumption of pornography. The chapter describes and analyzes the intense debates that followed this process, the feminist struggle against launching a Playboy TV channel in Israel, in particular. The feminists’ and ultra-orthodox parties’ joint success in passing a law against broadcasting pornography in Israeli television is also discussed. We point to the crucial contribution of Playboy to the legitimization of pornography as a leisure activity. Proposing the notion of repressive leisure, we argue that Playboy preserves male dominance and female subordination and exploitation. Moreover, Playboy, as part of the sex industry, reflects a backlash against women’s strengthening in society. Based on personal involvement in the struggle against Playboy in Israel, and on feminist anti-pornography scholarship, we emphasize the power of patriarchy to preserve male sexual predominance while degrading female human dignity. Liberal feminist activists who denounce anti-porn censorship and support sex consumers’ free choice, rather than promoting legislation against objectification of women, are critically discussed. We also contend that in considering Playboy as harmless leisure that should enjoy freedom of expression, the Israeli Supreme Court paved the way for pornography to thrive in Israel.