Pleomorphic adenoma of breast (PAB) is a rare mammary tumor of a mixed epithelial-myoepithelial nature. We report two patients with PAB, one of which is male. We believe our male patient is the sixth case of PAB in male breast in the literature. The two cases expressed heterogeneous clinical and radiological characteristics while showing similar histology and immunohistochemical staining profile. The first case was managed with surgical resection while the second underwent interventional radiology excision. PAB is usually a benign entity with occasional cases of recurrence. Malignant transformation is rare but has been reported in a few cases.