Obesity has been steadily increasing over the last three decades and is one of the leading causes of increased health costs due to its associated comorbidities. Unfortunately, conservative treatment including lifestyle changes did not achieve the desired results. Bariatric surgery, on the other hand, has emerged as an effective and safe treatment for obesity and its related comorbidities such as type 2 diabetes. Much time has passed since the first Roux-en-Y gastric bypass was performed in the 1960s, and the operation technique has since evolved. New variations such as the distal gastric bypass as well as the omega loop bypass have been developed. Today, the laparoscopic gastric bypass is still the most widely applied bariatric operation technique, followed by laparoscopic sleeve gastrectomy and laparoscopic adjustable gastric banding. The refinement of the surgical technique and the introduction of laparoscopy have resulted in low perioperative morbidity and mortality after gastric bypass surgery. In this article, we will be discussing the history of gastric bypass surgery as well as presenting current data on excessive weight loss and resolution of comorbidities with a focus on diabetes. We will be looking into newer techniques such as omega loop bypass and their efficacy compared to the standard gastric bypass. Furthermore, we will be addressing the most important early and long-term complications, their diagnostic strategies as well as their management.