This paper explores three currents in Iran’s contemporary intellectual landscape. Each of these promotes divergent outlooks and analyses of the present state of Iranian intellectual thought. However, I argue that the underlying epistemological outlook of these three currents vacillates between two extremes: that optimistic epistemology (as described by Karl Popper), which is the notion that humans can discern the truth of reality and thus be free, and pessimistic epistemology, an underlying disbelief in human’s ability to discern truth. As such, these three intellectual trends all may be undermining to a limited but growing trend towards critique, critical thinking, and more specifically, critical rationalism in the Iranian intellectual and political scene. The three trends this article discusses are the following: First, the post-Marxist/post-modern literature proffered by a group of young authors and translators primarily identified with the thinker Morad Farhadpour. Their work appears via articles, classes, public seminars, and, most prominently, translations (favored writers to translate include Alan Badiou, Giorgio Agamben, Zizek, Slavoj, and Theodor Adorno). Second, I explore the promotion of neoliberal-economic intellectualism offered by a number of authors, prominently Musa Ghaninejad, who argues that the solutions to Iran’s contemporary social ills lie in a redoubled focus on economic success rather than any intellectual effort. Lastly, I examine the theories of Seyed Javad Tabatabai, a prolific scholar of Islamic and political philosophy who also offers public classes. In order to tease out the tensions and underlying similarities between these three intellectual trends, I examine their thinking around three core topics: 1) Iranians’ relationship with “the West” and, accordingly, their relationship with modernity, 2) the proper role of the intellectual and the value of intellectual activity, and 3) the social responsibilities assigned to the average citizen/consumer of these respective theories. Research for this paper is based on ethnographic research in Tehran over the course several months, including participant observation in relevant classes and seminars, interviews with individuals involved in promoting each of these three outlooks, and analysis of relevant articles and books. I ultimately suggest that these three trends may pose a potential threat to the growth of critical thinking, and more significantly, to the tenuous hope that has appeared on the Iranian sociopolitical scene in recent years.