Background: Chronic disease risk factors tend to cooccur. Purpose: This study examined the cooccurrence of 8 negative health behaviors in a representative sample of urban adolescents to inform educational interventions. Methods: The prevalence, cooccurrence, and clustering of suicide attempt, lifetime history of sexual activity, tobacco use, cell phone use while driving, risky weight loss, daily soda consumption, sedentary behavior, and extreme video game use were examined among 1354 high school students. Results: Fifty-three percent of the sample were female and 61% were black. Most (80.3%) engaged in 1 to 3 risk behaviors, 10.4% reported none, and 0.5% had engaged in 6 to 8. Ever having sex was the most common cooccurring risk behavior and 4 distinct clusters of risk behaviors emerged: cluster 1 (N = 325) ever having sex; cluster 2 (N = 236): frequent soda drinking; cluster 3 (N = 402): sedentary + extreme video game use; cluster 4 (N = 391): current smoking + attempted suicide + cell phone use while driving + risky weight loss. Discussion: Adoption of multiple risk behaviors is common in youth. A history of sexual activity may be a risk behavior that is shared across different clusters of risk behaviors. Translation to Health Education Practice: Programming designed to address multiple risk behaviors concurrently in youth may be warranted.