Results suggest that chronic, uncontrollable stressors are significantly related to hopelessness in low-income urban youth. Active, distraction, and social-support-seeking coping exacerbate the association between uncontrollable stressors and hopelessness for boys, and rumination exacerbates the association between uncontrollable stressors and hopelessness for girls. Protective effects did not emerge for any of the coping strategies examined. For boys, the association between uncontrollable stressors and hopelessness was stronger for those boys who reported using more active coping. Active coping in the face of uncontrollable stressors may reinforce an adolescent’s sense that they are helpless to reduce levels of stress, even when they make a direct effort at doing so. Specifically, the association between uncontrollable stressors and hopelessness was stronger for those boys who reported using more social support-seeking coping. Distraction coping also emerged as a moderator for males; the association between uncontrollable stressors and hopelessness was stronger for those boys who reported using more distraction coping. Males were more likely than females to use distraction coping strategies. The most frequent distracting activities reported by both males and females in this sample were listening to music, watching television, and engaging in video games. Adolescent boys who engage in media-based distraction strategies may find themselves caught in a negative cycle; the coping strategies they use to distract themselves from uncontrollable stressors in their environment actually exacerbate their symptoms. Males who experience high levels of uncontrollable stress and utilize high levels of distraction coping via the media may engage in higher than average levels of aggressive and risky behaviors. Engaging in high-risk behavior may lead to exposure to additional stressors, and consequently, higher levels of hopelessness. Whereas females also reported media as their most common method for distraction, distraction coping did not moderate the relation between uncontrollable stressors and hopelessness for girls. Tables, references