The prevalence of childhood overweight is a major social and public health issue, and primary assessment should focus on early and middle childhood, because weight gain in these phases constitutes a strong predictor of subsequent negative outcomes. Studies on community samples have shown that growth curves may follow linear or non-linear trajectories from early to middle childhood, and can differ based on sex. Overweight children may exhibit a combination of physiological and psychosocial issues, and several studies have demonstrated an association between overweight and internalizing/externalizing behavior. Nevertheless, there is a dearth of longitudinal studies on depressive and aggressive symptoms in children with high BMI. This study adopted a growth curve modeling over three phases to: (1) describe BMI trajectories in two groups of children aged 2–8 (overweight and normal weight) from a community sample; (2) describe the developmental trajectories of children’s aggressive and depressive symptoms from 2 to 8 years of age. Results indicate higher BMI in 2-year-old girls, with males catching up with them by age 8. While overweight females’ BMIs were consistently high, males’ increased at 5 and 8 years. The mean scores for aggressive symptoms at T1 (2 years of age) were the same in all subjects, but a significant deviation occurred from T1 to T2 in both samples, in divergent directions. With regards to children’s depressive symptoms, the two groups had different starting points, with normal weight children scoring lower than overweight youths. Overweight females showed lower depressive scores than overweight males at T1, but they surpassed boys before T2, and showed more maladaptive symptoms at T3. This study solicits professionals working in pediatric settings to consider overweight children’s psychopathological risk, and to be aware that even when children’s BMI does not increase from 2 to 8 years, their psychopathological symptoms may grow in intensity.