Background: Overweight adolescents engage in risk behaviors at different rates than healthy-weight peers. Most extant research has focused on white or regional samples. Purpose: This article examined associations between weight and risk behaviors and determined whether associations differ by race/ethnicity. Methods: Youth Risk Behavior Survey data (N = 12,301) were used to compare substance use, sexual, and violent behaviors across weight status. Chi-square tests and logistic regression were used to investigate associations between weight and risk behaviors among white, black, and Hispanic adolescents. Results: Overweight and obese adolescents reported a higher prevalence of early cigarette, alcohol, and marijuana use. Compared with healthy-weight peers, obese males reported greater odds of weapon (odds ratio [OR] = 1.54; 95% confidence interval [CI], 1.28-1.87) and gun (OR = 1.51; 95% CI, 1.11-2.04) carrying, and obese females had elevated odds of weapon carrying (OR = 1.75; 95% CI, 1.22-2.51) and fighting (OR = 1.39; 95% CI, 1.08-1.79). These patterns were significant largely, though not exclusively, among white adolescents. Discussion: Overweight and obese adolescents tended to initiate risk behaviors earlier and engage in violent behaviors at higher rates. These trends appear most saliently among white youth. Translation to Health Education Practice: Early adolescence is a critical time to prevent health risk behaviors, and prevention efforts should consider gender, weight status, and race.