While recent research on the personalization of politics suggests that the lead candidates of parties competing for power have gained in importance both for the structure of electoral campaigns and results, they have never been unimportant. This paper looks into the political features of Austrian and German post-war opposition chancellor candidates, i.e. the parties’ lead candidates reaching out for the top job in the executive branch. While the obvious institutional similarities between the Austrian and German political systems - including parliamentary government, PR and federalism - would suggest the existence of similar patterns in the track records and political status of chancellor candidates, major differences between the candidates from both countries abound, which points to the limits of purely institutional explanations. That said, party-centered hypotheses do not fare much better either. There are few distinct differences at the level of lead candidates relating to different party families, and those that stand out contradict theoretical expectations. The obvious problems of relating empirical patterns to theoretical propositions marks a more general feature of opposition research and may not only be due to political contingency. Indeed, political challengers may have a vital interest to reserve a strategic element of unpredictability in their actions.