Male breast cancer is a rare disease. As a consequence, male breast cancer is often recognized later, and most patients present at an advanced clinical stage. We report the cases of two men with stage IV hormone receptor positive breast cancer who had both received at different times both systemic endocrine therapy with an aromatase inhibitor and gemcitabine as well as nab-paclitaxel-based combination chemotherapy. Although the aromatase inhibitors such as anastrozole, exemestane, and letrozole are very active in postmenopausal women with hormone receptor positive breast cancer, their efficacy in male breast cancer has not been demonstrated in phase II or III trials. Moreover, Gemcitabine and nab-paclitaxel every 14 days, with or without bevacizumab, are an active combination in male metastatic breast cancer and should be considered as an option in patients with extensive visceral metastases or hormone refractory disease.