Skin metastases from visceral malignancies have been well documented in the literature, and may be the presenting sign of an occult internal malignancy. Lung cancer in particular is a relatively common cause of skin metastases, which are considered a poor prognostic sign. Rarely, patients with lung cancer develop a second primary lung cancer that may require a novel chemotherapeutic regimen. The frequency of second primary malignancies presenting with metastatic skin lesions is not documented in the literature. We present a case of a 50-year-old man with a history of metastatic lung adenocarcinoma who was referred for evaluation of a nodule overlying his right mandible, which had been progressively enlarging for two weeks. Biopsy demonstrated metastatic squamous cell carcinoma. Subsequent CT-guided biopsy of a left retroperitoneal lymph node was conducted and notable for squamous cell carcinoma. Therefore, this patient's skin lesion was the presenting sign of a second primary visceral tumor, likely originating in the lung. We present this case to raise clinical awareness of the rare phenomenon that cutaneous metastasis may be the first sign of a visceral cancer, even in the setting of a previous distinct primary malignancy.