Understanding the individual factors that predispose persons to criminal behaviour is vital to reducing offending and rehabilitating those who have been sentenced to prison. This study examined the roles of narcissism (at both clinical and subclinical trait levels) and empathy, by comparing levels in young adult males currently serving a prison sentence to those with no history of criminal convictions. Prison participants had significantly higher levels of narcissism—in particular entitlement—than control participants, and this link was sequentially mediated by lower perspective-taking and subsequently lack of empathic concern. Trait narcissism showed stronger effects than narcissistic personality disorder symptoms. Narcissistic young men's feelings of entitlement and ensuing lack of empathy for others may account for their greater likelihood of criminal behaviour. Copyright © 2013 John Wiley & Sons, Ltd.