This article provides a cultural analysis of Italian leadership from a cross-cultural perspective. Americans view Italian leaders with cultural lenses and stereotypes often exaggerated by the media. Effective cross-cultural, business and international relations with Italians and Italian descendants require awareness of the true cultural dimensions beyond stereotypes and media portraits. Through the examination of Geert Hofstede’s cultural dimensions and the Global Leadership and Organizational Behavior Effectiveness (GLOBE studies), this study reviews the cultural dimensions called power distance, uncertainty avoidance and masculinity in relation to Italian leadership. From a cross-cultural and American standpoint, the author provides a cultural analysis of globally recognized Italian cultural dimensions that explain and enlighten more effective leadership practice and communication across borders and cultures.