Metastatic spread into the brain is not infrequently seen in association with epithelial neoplasms such as lung and breast cancer, among others. In the majority of cases such spread entails a poor prognosis. Metastasic spread to the pituitary gland, specifically to the area of the infundibulum is, however, a more rare presentation. Most reported cases of metastatic disease to the pituitary are confined to the posterior lobe, probably related to the richer blood supply as compared to the anterior counterpart. The detection of pituitary metastasis is further complicated by the lack of specific associated symptomatology or definite radiologic diagnostic findings. We here describe the different clinical presentations of two patients with symptomatic pituitary stalk metastasis resulting from primary breast cancer; we also provide a systematic review of the literature.