Pyoderma gangrenosum (PG) is a cutaneous inflammatory disorder that results in painful ulcers. Isolated penile PG is an exceedingly rare entity that has only been reported in a handful of cases. This case highlights the course of a 71-year old man with a locally destructive, nonhealing penile ulceration who was ultimately diagnosed with PG. He underwent extensive work up to reach the diagnosis. His disease progression was halted with systemic steroids and Methotrexate. We present his clinical course and a review of the literature to highlight the need for early recognition of this potentially devastating condition and to outline management options.