Few benign melanocytic lesions encountered in clinical practice elicit the levels of angst, confusion, and controversy caused by Spitz nevi. This is partly because their clinical, dermoscopic, and histopathologic features can overlap with those of melanoma and partly because their biology and natural history are not fully elucidated. Although the term benign juvenile melanoma has been dropped in favor of Spitz nevus or epitheloid and spindle cell nevus, the original name for this lesion does, in fact, convey the conundrum physicians face when confronted with a spitzoid lesion. Is it truly benign? Does it represent a malignant tumor masquerading as a benign one? Can it transform into a melanoma?