Saxophone penis is a rare and severe manifestation of penoscrotal elephantiasis, characterized by marked penile deformity resembling a saxophone. It results from chronic lymphatic obstruction and progressive fibrosis secondary to long-lasting inflammation, most commonly in the course of hidradenitis suppurativa. Hidradenitis suppurativa is a chronic inflammatory dermatosis leading to the formation of painful nodules, abscesses, sinus tracts, and scarring, predominantly affecting intertriginous areas such as the axillae, groin, and perineum. We describe 2 cases of saxophone penis secondary to advanced penoscrotal hidradenitis suppurativa. The first patient was a 33-year-old man with a 1.5-year history of untreated disease, presenting with severe penoscrotal lymphedema and penile deformity requiring surgical intervention. The second was a 58-year-old man with a 20-year history of progressive hidradenitis suppurativa and massive penoscrotal involvement. Both patients experienced substantial physical and psychological burden, highlighting the importance of early recognition, appropriate systemic treatment, and multidisciplinary management.