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Nevus sebaceous of Jadassohn (NSJ) is a cutaneous hamartoma of pilosebaceous origin that differentiates into multiple neoplasms, most commonly trichoblastoma/basal cell carcinoma and syringocystadenoma papilliferum (SCAP). Malignant transformation of NSJ is rare and usually observed in the elderly. However, a diagnosis of more than three separate tumors concurrent to multiple malignancies developing from a single NSJ is extremely rare. We here report a case of a 72-year-old male patient with five distinct tumors arising from NSJ of the scalp, including SCAP, tubular apocrine adenoma, eccrine poroma, apocrine cystadenoma, and cutaneous apocrine carcinoma.