Given the history of charismatic dictatorship in this century, charismatic leaders have been seen as threats to democracy. At the same time, periods of accelerated political change, such as the period of post Communist democratization in Eastern and Central Europe, also give rise to charismatic leaders. This pa per establishes the conditions under which charismatic leaders are compatible with democracy. Using a framework drawn from Max Weber's sociological writings, the paper argues that charismatic leadership is only compatible with democracy when charisma is routinized in a rational-legal direction. In that routini zation, however, rational-legal procedures (the rule-boundedness of power) must predominate over charis matic elements (the arbitrary and personal exercise of power). When this balance is reversed the result will be dictatorship. This discussion highlights the fact that both modern dictatorship and democracy legit imate themselves by a combination of charismatic and rational elements. It then considers whether We~ ber's theory can help us to understand the impact of the charismatic leadership on post-communist democ ratization by considering the experience of Havel in the Czech Republic, Walesa in Poland, and Yeltsin in Russia. It concludes with a discussion of charisma and its role in both democracy and dictatorship in the contemporary era. It finds that the similarity in the way in which modem democracy and dictatorship are legitimated augurs better for the viability of authoritarian regimes than the many recent accounts predict ing a diminished prospect for dictatorship in the current era might suggest.