Attempts to "cure" erectile dysfunction (ED) are as old as recorded history. The history of penile prosthetic devices dates back over 500 years, when a French military surgeon designed the first known wooden prosthesis to support micturition. There have since been a great many technological advancements in penile prosthetics. Penile implants for the improvement of sexual function date to the twentieth century. Like all human endeavors, penile prosthesis innovations have progressed via trial and error. This review aims to provide an overview of penile prostheses for the treatment of ED since their introduction in 1936. More specifically, we aim to highlight important advances in penile prosthesis development and discuss dead ends that were abandoned. Highlights include two-piece inflatables, three-piece inflatables, and malleable/semirigid, along with modifications and updates to each basic design that improved both insertion and usability. Dead ends include innovative ideas that were lost to history due to a variety of factors. We also look to the future and discuss expected advances, including remotely activated devices and prostheses designed for special populations, including transgender men.