US economic policy in the late twentieth century privileged the financial sector by advancing generous tax breaks for wealthy Americans and traders, and prioritizing union-busting and cuts to social programs, producing a violence of deprivation against the poor and marginalized others. Simultaneously, the Reagan administration sought to shore up its political coalition in the post-Watergate era by appealing to a newly engaged Christian right with conservative social policies including pushback against the sexual revolution and the formation of the Meese Commission to study restrictions on pornography. These significant changes in culture found their way into a wealth of media including journalism, films, and novels that processed the seemingly contradictory moral claims underlying these policies: greed is good; sex is bad. This article draws on financial and literary theory to examine how two iconic novels from the era, Tom Wolfe’s The Bonfire of the Vanities (1987) and Bret Easton Ellis’s American Psycho (1991), exploit representations of sexualized violence to ramify and then explore the latent links among sex, violence, and finance. Each novel satirizes Wall Street’s violent indifference by embodying it in a figure of elite, white masculinity whose privilege is expressed through sex. The novels’ critiques, however, turn out to be self-contradictory, as their disavowal of the fictionality of finance is bound up with a concomitant investment in regressive sexual politics. In so doing, the novels demonstrate that culture-industry efforts to push back against economic deregulation may be allied with the cultural systems that support that deregulation or enable it.