Objectives: Late adolescence represents a developmental risk period when many youth become involved in multiple forms of high-risk behaviors with adverse consequences. This study assessed the degree to which two such behaviors, adolescent sexual behaviors and gambling, were associated in a community-based sample with a large African-American presence. Study design: Data are derived from a cohort study. This study focuses on 427 African-American participants with complete information on gambling and sexual behaviors by age 18 (72% of original cohort). Gambling involvement and related problems were based on responses to the South Oaks Gambling Screen -Revised for Adolescents. Several questions assessed sexual behaviors, including age of initiation. Multivariable logistic regression models adjusted for demographics, intervention status, impulsivity, depressive and anxiety symptoms, and alcohol and illegal drug use. Results: Almost half of the sample (49%, n = 211) had gambled at least once before age 18. More gamblers than non-gamblers had initiated sexual intercourse by age 18 (aOR: 2.29 [1.16, 4.52]). Among those who had initiated sexual activity, more gamblers than non-gamblers with high impulsivity levels at age 13 (vs. low impulsivity levels) had become pregnant or had impregnated someone. Among those who had initiated sexual activity by age 18, more male gamblers had impregnated someone by age 18 as compared to female gamblers becoming pregnant. Conclusions: Gambling and sexual behaviors often co-occur among adolescents. Such findings prompt the need for the inclusion of gambling, an often overlooked risky behavior, in behavioral prevention/intervention programs targeting adolescents.