Understanding a variety of scrotal diseases is essential to developing an accurate differential diagnosis and is critical in providing optimal patient care. Ultrasound is the imaging modality of choice when evaluating for scrotal pathology, with the major purpose of locating such pathology to either the testis, or epididymis, or other intrascrotal structures, as well as characterizing lesions as solid or cystic. It is generally assumed that most solid intratesticular masses are more likely malignant, whereas most extratesticular ones are benign, although some exceptions to that rule exist. This pictorial essay will focus on rare and less commonly encountered benign and malignant testicular and paratesticular pathologies, which may pose a diagnostic dilemma for interpreting radiologists and treating physicians. Knowledge of their imaging characteristics will help narrow the differential diagnosis and assist in proper patient management and care.