Perspective-taking, by means of creating an overlap between self and other cognitive representations, has been found to effectively decrease stereotyping and ingroup favoritism. In the present investigation, the authors examined the potential moderating role of self-esteem on the effects of perspective-taking on prejudice. In two experiments, it was found that perspective-takers, but not control participants, with temporarily or chronically high self-esteem evaluated an outgroup more positively than perspective-takers with low self-esteem. This finding suggests an irony of perspective-taking: it builds off egocentric biases to improve outgroup evaluations. The discussion focuses on how debiasing intergroup thought is often best accomplished by working through the very processes that produced the bias in the first place.