Penile cancer is a rare malignancy and a debilitating condition in most industrialized nations that often requires aggressive surgical or multimodal treatment with significant anatomical, functional, and psychosocial impact on patients’ quality of life. Total or partial penile amputation has been considered the standard of treatment according to locoregional clinical staging and risk stratification. However, these surgical options are associated with significant negative functional and psychological outcomes in terms of body image, self-esteem, and manhood resulting in loss of sexual function and inability of upright voiding. Recently, a critical paradigm shift has taken place in the clinical management of penile malignancy, that is, the implementation of alternative, less-invasive surgical strategies to deal with the primary malignancy. These sparing approaches of penile anatomy aim to retain penile and urinary functions and overall quality of life and thus interfering as little as possible with functional anatomy. This paradigm shift has been made possible by advances in surgical and technological developments which have resulted in organ-preserving strategies with gratifying psychosocial and functional outcomes simultaneously without compromising final cancer control. This spectrum of novel surgical strategies includes local excision, glansectomy, and partial penectomy followed by surgical reconstructive procedures consisting of primary closure of the resulting defect, closure with skin flaps or split- thickness skin grafts, penile lengthening and/or enhancing procedures, neophalloplasty, and, more recently, penile transplantation fostered by limitations of conventional reconstruction. This review discusses the complexities of surgical reconstruction following penile cancer treatment including the burgeoning field of penile transplantation.