Hypertension, a prevalent risk factor for cardiovascular disease, frequently occurs in conjunction with metabolic disturbances and in particular with dyslipidaemia; such comorbidity presents in more than one-third of hypertensive patients. Moreover, hypertension and dyslipidaemia often manifest concomitantly in the clinical context of obesity and insulin resistance. In this setting, distinct metabolic anomalies may account for the development of both conditions, and may equally act to exacerbate their effects on vascular dysfunction. Significantly, hypertension and dyslipidaemia are linked mechanistically and may act in synergy at the arterial wall to enhance atherosclerosis. In this review, we identify potential mechanisms underlying the pathophysiological interaction between hypertension and dyslipidaemia at the cellular and molecular levels, and which may underlie elevated cardiovascular risk in obesity and insulin resistance. Finally, the clinical evidence supporting the beneficial effects of an integrated pharmacotherapeutic strategy to the reduction of cardiovascular risk in patients with insulin resistance, type 2 diabetes and the metabolic syndrome is critically discussed.