Parotid masses coincided with skin tumors in head and neck region may represent a serious diagnostic challenge. Conventional imaging modalities such as computed tomography, magnetic resonance imaging may help to determine nature of the masses. Positron emission tomography - computed tomography imaging is reported to be useful for the detection of malignancy in the parotid gland. But in some situations all of them become insufficient. We present a case of cheek malignant melanoma with an incidentally discovered parotid mass during the investigation. We describe the problems experienced in the course of differential diagnosis and decision making in terms of surgical management. As a result, the most reliable diagnosis of suspicious parotid lesions accompanying head and neck melanomas comes from frozen section analyses. The other diagnostic tools are not reliable enough to allow a safe surgical plan in terms of regional treatment; however, the significance of positron emission tomography - computed tomography in distant metastasis investigation should always be kept in mind.