This research work integrates James Messerschmidt’s Masculinity Theory (1997) with Robert Agnew’s General Strain Theory (1992) to examine the relationship between failure to achieve ideal masculine standards, resultant psychological stressors, and the decision to engage in illicit drug activity. OLS and Binary Logistic Regression was performed on a sample of male college students (N = 851) to examine three hypotheses. Findings support the hypothesis that a positive relationship exists between failed masculinity and negative emotions. Partial support was found for the hypothesis that a positive relationship exists between negative emotions and drug trafficking. Partial support was also found for the hypothesis that negative emotions mediate the relationship between failed masculinity and selling drugs. Further examination of these relationships is encouraged.