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In the Roman Empire, philosophy was as much a brand, an aesthetic, or even a viral sensation as it was an academic discipline. Not so much interested in approaching philosophy as an academic discipline as much as a cultural phenomenon, I argue that there is much to learn from the various iterations of “pop” philosophy in the ancient world, focusing on works that feature philosophy, but are not themselves philosophical treatises in the strict sense. The sophistical, rhetorical, and generally exaggerated works of this era do not simply recapitulate tired stereotypes, but rather prompt metaliterary reflection on complex philosophical ideas and the role of philosophy in the Roman world. I suggest that philosophy was more than an intellectual or academic discipline; it also exerted considerable influence over its fans and was an important form of social capital. Individuals could also cultivate personal relationships with philosophy in various ways. For example, Seneca the Younger describes his collection of statues of various philosophers as his “friends” who inspire him to come up with new ideas of his own, not simply repeat the ideas of the past (Ep. 64). In the first two chapters, I focus on sophistical and satirical depictions of philosophy and philosophers, highlighting the frequent disconnect between philosophical principles and commonsense “wisdom” in a sense that is more general yet, as these authors seek to show, more practical. In the second two chapters, I suggest that ancient intellectuals envisioned philosophy as an entity that has a physical presence in the world, analyzing both personifications of philosophy in literature and the real-life monuments constructed to philosophy in antiquity and in modernity. In conclusion, the phantasia (appearance or imagined form) of philosophy was always “trending” in the Imperial era. It took on a life of its own and was a source of innovation and creativity. Ultimately, representing philosophy in the Second Sophistic was an endeavor that resulted from a complex and inextricable interplay between intellect and imagination.