The purpose of this explorative study is to put the existing theories on charismatic political leadership in a current post-web media context. It also seeks to better understand why “charismatic politicians” seem to have success in present-day cyber politics. The paper considers political charisma in a Weberian perspective and aims to explain what elements it includes in a current electoral environment characterized by a fast-changing media landscape. The paper places the existing theoretical models in the context of two European societies, by comparing Estonia and Italy as case studies. Estonia, a small ex-Soviet country has emerged in recent years as an advanced e-society with highly “internetisized” media. At the same time, Italy became known by the phenomenon of the “Berlusconization” of the media, a popular subject of study in political communication. The analysis considers existing research, mostly based on the work of Max Weber, and aims to test the index of charisma, developed by Pappas (2011), in the two observed countries. The paper concludes with a discussion on if and how charismatic political leaders fit a deliberative democracy. Finally, attention is drawn to the need for further systematic comparative research to better understand the phenomenon of charismatic leadership in the post-web media environment.