Abstract Background We aim to study the “golden youth” hypothesis and examine the risky behaviors of adolescents with high socioeconomic position (SEP) in post-Communist countries of Europe (PCCE) in relation to income inequality. Methods Adolescents aged 11-15 years from 14 PCCE participating in the Health Behavior in School-aged Children survey 2017/18 were included. A K-means cluster analysis was conducted to group adolescents based on tobacco smoking, alcohol use, binge drinking, and bullying perpetration. Generalized linear mixed models were fitted. Results Four clusters of adolescents were identified. The percentage of high-SEP adolescents in Cluster 1 (low risky behaviors) was slightly less compared to middle and low-SEP groups (70.9% vs 73.1% vs 73.9%, respectively). High-SEP adolescents were more likely to be in Cluster 2, characterized by frequent alcohol consumption but moderate binge drinking (14.3% vs 12.6% vs 10.7%). The prevalence of risky behaviors was similar between high and low-SEP adolescents in Cluster 3 (high smoking, frequent alcohol use, binge drinking, and moderate bullying) (8.0% vs 7.7% vs 8.2%) and Cluster 4 (high levels of bullying perpetration) (6.7% vs 6.5% vs 7.2%). Countries with higher Gini index were at a greater risk of reporting risky behaviors. High-SEP adolescents were more likely to engage in risky behaviors in countries with high income inequality. The odds ratios comparing high- vs. low-SEP adolescents ranged from 0.89 in the least unequal to 1.67 in the most unequal countries for multiple risky behaviors (Cluster 3: P-interaction = 0.042) and from 0.61 to 1.19 for bullying perpetration (Cluster 4: P-interaction = 0.030). Conclusions High-SEP adolescents in PCCE might be at an increased risk for unhealthy and vicious behaviors, especially in countries with high income inequality. This study highlights the need for policies that address income inequality to ensure the well-being of adolescents across socioeconomic strata in PCCE. Key messages • High-SEP adolescents might be at an increased risk for unhealthy behavior in PCCE. • Wide income inequality might contribute to risky behaviors among high-SEP adolescents.