Orthognathic surgery has been performed for over two centuries with the first procedure occurring in the 1860s. It was not until the late 1950s with the pioneering work of Obwegeser that the modern orthognathic surgery era began. From the beginning, oral surgeons and orthodontists have worked in parallel fashion; advances in both disciplines have led to what is now routinely performed. New and exciting developments are underway not only in diagnosis but also in treatment planning with computer aided surgical simulation and the use of artificial intelligence (AI) to enhance patient treatment outcomes. The purpose of this article is to briefly review the history of orthognathic surgery, to examine the present status and to highlight emerging technologies and advancements.