The diagnosis of pigmented basal cell carcinoma can bring significant distress to patients and physicians alike. However, astute clinicians that can employ correctly the clinical and dermatoscopical clues can reach a correct preoperative diagnosis, and as such can avoid unnecessary worry for the patient, additional work-up, or overtreatment. We present a case series of pigmented basal cell carcinomas and a comparative case with pigmented cutaneous melanoma, together with a literature review, that will highlight these aspects of the management of pigmented tumours of the skin.