INTRODUCTION: This paper accomplishes two goals. First, we assesses the measurement invariance of legal cynicism among adolescents in São Paulo, Brazil, Montevideo, Uruguay, and Zurich, Switzerland. Second, we evaluate a series of social and individual antecedents that are expected to influence legal cynicism across contexts. METHODS: This paper first evaluates the measurement invariance of legal cynicism using Multigroup Confirmatory Factor Analysis with three randomized clustered samples of adolescents in Zurich (n = 1447), São Paulo (n = 2680) and Montevideo (n = 2204). Second, we assessed the correlates for legal cynicism in each city using structural equation modelling techniques. RESULTS: The results demonstrated metric invariance, but not scalar invariance among adolescents in São Paulo, Zurich, and Montevideo. We were able to establish partial measurement invariance for legal cynicism in São Paulo and Zurich, and therefore proceeded with the comparison of latent means and antecedents. The results show that on average legal cynicism is higher in Zurich, but that the size and strength of antecedents were similar across cities. Low self-control was by far the strongest correlate of legal cynicism. CONCLUSIONS: Overall, our results suggest that current operationalizations of legal cynicism may not be rooted in social structural context and experiences with legal authorities, but rather reflect how individuals interpret legal boundaries and dispositions towards rule-breaking. Researchers must reconsider how legal cynicism fits into models of legal socialization, and whether developmental models of self-control may help us understand the origins and nature of legal cynicism, as it is currently measured.