Parent-child agreement regarding emotional and behavioral problems in adolescents with obesity was measured. One hundred Italian adolescents with obesity (36 males, 64 females, mean age ± SD: 15.3 ± 1.61 years, mean body mass index, BMI: 37.9 ± 5.48 kg/m2), hospitalized for a 3-week multidisciplinary body weight reduction program at Istituto Auxologico Italiano, Piancavallo-Verbania, Italy, and one of their parents (n = 100, 40 fathers, 60 mothers) participated in the study. Achenbach's Child Behavior Checklist (CBCL) for parents and the Youth Self Report (YSR) for teens were administered. Most of the CBCL and YSR scores were normal, with more borderline and clinical scores being found in CBCL (29% of borderline scores in attention problems, 28% in affective problems, and 26% in ADHD; 32% of clinical scores in affective problems, 23% in withdrawn/depressed, and 22% in anxiety problems and somatic complains subscales) than in YSR (19% of borderline scores in affective behaviors and 17% in somatic complains; 15% of clinical scores in anxiety problems and 17% in withdrawn/depressed subscale). Young females reported greater anxiety problems (p = 0.009), oppositional defiant problems (p = 0.029), anxiety/depressed (p = 0.030), and internalizing problems (p = 0.045) than males. Pearson's coefficients ranged between 0.273 to 0.517. This study provides information on the cross-informant evaluation of psychological profiles with CBCL and YSR in a clinical sample of adolescents with obesity and their parents.