Knowledge of anatomic variations concerning head and neck veins is important to surgeons performing interventions in these regions, as well as to radiologists. The retromandibular vein is used as a guide to expose the facial nerve branches inside the parotid gland, during parotid surgery and open reduction of mandibular condyle fractures. It is also used as a landmark for localisation of the nerve and compartmentalisation of parotid gland lesions preoperatively, during computed tomography, magnetic resonance imaging and sonography. In this paper, the anomalous retromandibular vein's course on the left side of a male cadaver is described. The vein was formed around the nerve, while the maxillary vein travelled medial to the facial nerve branches and superficial to the superficial temporal vein. Interestingly, the facial nerve temporofacial division crossed again the superficial temporal vein upwards, forming a "nerve fork". The incidence of the reported variability of the relationship between the retromandibular vein and the facial nerve are discussed with a detailed literature review. Accordingly, the typical deep position of the retromandibular vein in relation to the facial nerve is estimated to 88.17% to all sides. Furthermore, an updated classification system is proposed, including 4 types and subtypes.