This study extends past findings of heightened problems among affluent youth by examining adjustment patterns among boys in two academically elite, independent high schools: one for boys only and the other co-educational. Both samples manifested disproportionately high rates of internalizing and externalizing symptoms, but only the co-educational boys showed elevations in substance use. Boys in both schools showed elevations in a new outcome domain examined: exhibitionistic narcissism. Multivariate analyses of predictors showed that parent criticism--a defining feature of youths' maladaptive perfectionism--and perceived maternal depression emerged as major vulnerability factors for both samples in relation to symptom levels. On other parenting dimensions, boys in the single-sex school seemed to be particularly sensitive to feelings of alienation from their fathers and perceived paternal depression. Envy of peers' attractiveness was associated with adolescent distress in both samples, but appeared to be especially critical for co-educational boys. Results are discussed, focusing on the costs and benefits of boys' attendance at a single-sex versus co-educational school, along with implications for practice and future research.