This review focuses on the associations between testosterone, insulin resistance and metabolic syndrome in men. Testosterone deficiency may contribute to the development of the metabolic syndrome, especially to the accumulation of intra-abdominal (visceral) adipose tissue and insulin resistance. On the other hand, inflammatory and metabolic disorders associated with visceral intra-abdominal tissue contribute to the generation of hypogonadism. This review discusses some possible pathophysiological mechanisms underlying this vicious cycle. Some studies have suggested the use of testosterone substitution in order to prevent or attenuate metabolic syndrome. However, data on testosterone substitution are still controversial and larger controlled trials are needed to establish the population with the optimal benefit/risk ratio.