Transorbital surgery has gained recent notoriety because of its incorporation into endoscopic skull base surgery. The use of this surgical corridor has been pervasive throughout the 20th century. It has been utilized by multiple disciplines for both clinical and experimental purposes, although its historical origin is medically and ethically controversial. Hermann Knapp first introduced the orbital surgical technique in 1874, and Rudolf Krönlein introduced his procedure in 1889. Rivalry between Walter Dandy in neurosurgery and Raynold Berke in ophthalmology further influenced methods of tackling intracranial and intraorbital pathologies. In 1946, Walter Freeman revolutionized psychosurgery by completing seemingly successful transorbital leucotomies and promoting their minimally invasive and benign surgical characteristics. However, as Freeman’s legacy came into disrepute, so did the transorbital brain access corridor, again resulting in its stunted evolution. Microsurgery and endoscopy further influenced the use, or lack thereof, of the transorbital corridor in neurosurgical approaches. Historical analysis of present goals in modern skull base surgery echoes the principles established through an approach described almost 150 years ago: minimal invasion, minimal morbidity, and priority of patient satisfaction. The progression of the transorbital approach not only reflects psychosocial influences on medical therapy, as well as the competition of surgical pioneers for supremacy, but also describes the diversification of skull base techniques, the impact of microsurgical mastery on circumferential neurosurgical corridors, the influence of technology on modernizing skull base surgery, and the advancing trend of multidisciplinary surgical excellence.