Growing evidence suggests heterogeneity within interpersonal-callous (IC) youth based on co-occurring anxiety. The developmental validity of this proposed taxonomy remains unclear however, as most previous research is cross-sectional and/or limited to adolescence. We aimed to identify low-anxiety (IC/ANX-) and high-anxiety (IC/ANX+) IC variants, and compare these groups on (a) early risk exposures, (b) psychiatric symptoms from midchildhood to early adolescence, and (c) school-based functioning. Using the Avon Longitudinal Study of Parents and Children (ALSPAC), a prospective epidemiological birth cohort, model-based cluster analysis was performed on children with complete age-13 IC and anxiety scores (n = 6,791). Analysis of variance was used to compare resulting clusters on (a) prenatal and postnatal family adversity and maternal psychopathology, and harsh parenting; (b) developmental differences in attention-deficit/hyperactivity disorder (ADHD), conduct disorder (CD), oppositional defiant disorder (ODD), emotional difficulties, and low pro-social behavior at 7, 10, and 13 years; and (c) teacher-reported discipline problems, along with standardized test performance. We identified a 4-cluster solution: ‘typical,’ ‘low,’ ‘IC/ANX-‘, and ‘IC/ANX+.’ IC/ANX+ youth showed the highest prenatal and postnatal levels of family adversity and maternal psychopathology, highest levels of ADHD, CD, ODD, and emotional difficulties, greatest discipline problems, and lowest national test scores (all p < .001). IC/ANX+ also showed a distinct pattern of increasing psychopathology from age 7 to 13 years. Adolescent IC subtypes were successfully validated in ALSPAC across multiple raters using prenatal and early postnatal risk, repeated measures of psychopathology, and school-based outcomes. Greater prenatal environmental risk among IC/ANX+ youth suggests an important target for early intervention. Impact Statement General Scientific Summary-Children who display interpersonal callousness (IC; i.e., deceitful behavior, lack of empathy/remorse) have historically been thought to show reduced anxiety or fear. This study, however, identified a subgroup of youth who show IC alongside elevated anxiety. Compared to a low-anxiety IC group, these high-anxiety IC children experienced greater prenatal and postnatal adversity, presented higher levels of co-occurring psychiatric disorders, had greater behavioral problems at school, and performed worse in national standardized school tests.