To stand out, some organizations have started asking unorthodox interview questions to uncover unique qualities of the candidates while signaling the playful culture of their organization (e.g., “Would you rather fight a horse-sized duck or 100 duck-sized horses?”). Despite its growing popularity, there is no empirical research on the organizational impact of these unusual questions. In this paper, we introduce Oddball Personality Questions (OPQs) and a theoretical model of its impact on recruitment. We test our theoretical model had in two studies. In study 1 (n = 275), we found that compared to traditional interview questions, people judged OPQs to be less useful, but more likable. The negative effect of decreased usefulness judgments on organizational attraction was offset by the positive effect of increased likability judgments. Participants were not more attracted to organizations that asked OPQs. In study 2 (n = 266), using a multi-wave time-lagged study, we find job seekers with a greater sense of humor reported more favorable reactions toward Oddball Personality Questions and subsequent attraction to the organization. Despite the double-edged nature of OPQs for recruitment, we believe that its limitations outweigh the benefits. Until the validity of OPQs as an assessment tool is established, its use in employment interviews remains dubious and cannot be recommended.