Obesity is a growing epidemic both in Australia and worldwide. Being overweight or obese is known to be adversely associated with multiple cardiovascular risk factors, such as type 2 diabetes mellitus, lipid disorders and hypertension. Despite the adverse impact of overweight and obesity, recent observational studies have suggested that in some overweight and obese individuals with established chronic disease, there is a survival advantage that is paradoxically better than individuals of normal weight. A burgeoning area of interest is the existence of this paradox in chronic endocrine disorders, especially with respect to osteoporosis and type 2 diabetes mellitus, as well as the latter's chronic complications, chronic kidney disease and coronary artery disease. In this article, we review the postulated mechanisms and latest evidence concerning the obesity paradox, with a focus on endocrine-related diseases. We discuss confounders and biases that exist in observational studies from which the paradox has been described and highlight that, despite the observed paradox, substantial literature exists supporting the benefits of weight reduction in obesity.