We analyze the long-term effects of neighborhood poverty and crime on negative self-feelings of young adults. Cumulative and relative disadvantage explanations are tested with the interactive effect of (1) neighborhood and individual-level economic disadvantage and (2) neighborhood crime and economic disadvantage. Results from a longitudinal study following adolescents to young adulthood show that the development of negative self-feelings (a combination of depression, anxiety, and self-derogation) is determined by relative, rather than cumulative disadvantage. The poor in affluent neighborhoods have the highest negative self-feelings, while the relatively wealthy in poor neighborhoods have the lowest negative self-feelings. Similarly, we find the highest increase in negative self-feelings is found in an affluent neighborhood with crime and not in a poor neighborhood with crime.