Does an increasing emphasis on individual freedom in mass values erode or revitalize democratic societies? This paper offers a new approach to this debate by examining it through the lens of Isaiah Berlin, and his distinction between positive and negative freedom. I show that, contrary to the common assumption among scholars who study mass values regarding freedom, these do not consist of one dimension but two: negative and positive freedom. I also show that, while valuing negative liberty clearly leads a person to become more morally permissive and more condoning of non-compliance with legal norms, valuing positive liberty does not seem to have the same effects at all; in fact, it shows the very opposite relationship with respect to some of these attitudes. Thus, it matters what kind of freedom people value. The results rely on confirmatory factor and regression analyses on World Values Survey data from ten affluent Western countries in 2005–2006.