Growing evidence suggests that the general personality structure predisposes the political or ideological orientation. Here, we first replicated findings of associations between Big Five factors openness, agreeableness and conscientiousness, and self-reported political orientation in a large German sample. However, the new aspect of our study is the addition of Wahl-O-Mat (WoM; a prominent voting advice application) as a measure of concrete policy-positions. Here, a score of accordance between a participant’s and the several German parties’ stances on current and relevant policy-issues is computed. Given that political science identifies trends towards a dealignment of voters with political parties and a decreasing significance of socio-structural factors, an issue-based approach to vote choice may become critical in the future. Therefore, we investigated whether personality’s influence on political orientation also extends to stances about specific issues and, thus, is not restricted to self-placements. As expected, WoM-scores also showed meaningful correlations with personality traits: accordance with right-of-center-parties is negatively related to openness and agreeableness and positively related to conscientiousness. Finally, we recruited smaller samples in the United States, Denmark, Sweden, Turkey, Spain, Australia, and Bulgaria and showed that the associations mentioned above are cross-nationally replicable. We conclude that personality influences not only self-perceived political identity but also attitudes towards current issues of political controversy. In both cases, the effects of personality were mediated by Right-Wing-Authoritarianism and Social Dominance Orientation.