This article presents the first assessment of how the five‐factor model of personality and political ideology are associated across the world. Personality traits become more and more important in the study of political behavior. And the relationship with ideology virtually parallels the history of this line of research. Yet, many existing studies are limited to single, highly developed countries and mostly draw on nonrandom or nonrepresentative samples. Our study, in contrasts, makes use of the most recent wave of the World Value Survey and analyzes the relationship comparatively in 21 countries from all continents. Results corroborate the most prominent findings about personality and ideology. However, effects of personality traits cannot be generalized easily across the world as effects vary considerably from country to country. Therefore, we additionally analyze specific preferences concerning social and economic policies on the one side. On the other, we theorize as well as model the moderating role of the country context by introducing cross‐level interaction effects.