People often fail to empathize with others, and sometimes even experience schadenfreude—pleasure at others’ misfortunes. One potent predictor of schadenfreude is envy, which, according to the stereotype content model, is elicited by high-status, competitive targets. Here we review our recent research program investigating the relationships among stereotypes, envy, schadenfreude, and harm. Experiment 1 demonstrates that stereotypes are sufficient to influence affective responses to targets’ misfortunes; participants not only report feeling less negative when misfortunes befall high-status, competitive targets as compared to other targets, they also smile more (assessed with facial EMG). Experiment 2 replicates the self-report findings from Experiment 1 and assesses behavioral tendencies toward envied targets; participants are more willing to endorse harming high-status, competitive targets as compared to other targets. Experiment 3 turns off the schadenfreude response by manipulating status and competition-relevant information regarding envied targets. Finally, Experiment 4 investigates affective and neural markers of intergroup envy and schadenfreude in the context of a long-standing sports rivalry and the extent to which neurophysiological correlates of schadenfreude are related to self-reported likelihood of harming rival team fans. We conclude with implications and future directions.