In this paper I suggest that one of Kant's motives in framing the account of artistic genius that he presents in the Critique of Judgment was to respond to Herder's veneration of Shakespeare. Kant agreed with Herder that Shakespeare was an exemplary artistic genius, but he disagreed with him about the relationship between genius and philosophy. Herder shared Kant's view that beautiful art should not infringe on the boundaries of the sciences, but in Kant's view Herder's own speculative metaphysics violated this principle. Kant accused Herder of allowing his genius to interfere with his philosophy – that is, of philosophizing in a Shakespearean manner. Instead of attempting to adjudicate this debate, I try to show how Herder could have defended his position by reading Kant through the lens of Shakespeare's Henry IV Part 1. I conclude by briefly indicating how the debate between Kant and Herder came to inform the analytic/continental division, which in light of this debate can be understood as a meta-argument about the nature of philosophical arguments.