Pathological conditions affecting the male breast (MB) share some similarities with those found in women, while others are specific to men. The first part of this review provides an overview of MB disorders, exploring the most common types of MB diseases. The second part then emphasizes the state-of-the-art approaches proposed in the literature for screening and follow-up with MB cancer patients, which highlights the importance of tailored strategies for diagnosis, follow-up, and identifying high-risk populations. Considering the increasing attention in recent years on the topic, transgender individuals are also included in this review. Together with the MB, it is an understudied category thus far. This review aims to raise awareness among radiologists that MBs should be approached differently from female breasts, contributing to the advancement of medical knowledge, improving patient outcomes, and promoting early detection of MB disorders. The review also provides an update on breast cancer and screening in the transgender population.