The increasing worldwide prevalence of diabetes mellitus and obesity has projected concerns for increasing burden of cardiovascular morbidity and mortality. The dangers of obesity in adults and children have received more attention than ever in the recent years as more research data becomes available regarding the long-term health outcomes. Weight loss in obese and overweight subjects can be induced via intensive lifestyle modifications, medications, and/or bariatric surgery. These methods have been shown to confer overall health benefits; however, their effect on remission of preexisting diabetes mellitus and reduction in cardiovascular risk has been variable. Recent research data has offered a much better understanding of the pathophysiology and outcomes of these management strategies in obese patients. In this paper, the authors have summarized the results of major studies on remission of type 2 diabetes mellitus and reduction of cardiovascular events by weight loss induced by different methods. Furthermore, the paper aims to clarify various prevailing myths and practice patterns about obesity management among clinicians.