Most research into psychopathy among prisoners has almost entirely been based in Western countries, and it is unclear whether these research findings are applicable to other settings as well. The main aim of the current study was to survey the relationship between Five Factor Model and psychopathic personality in a sample of male prisoners in Iran. Participants (N = 202) completed the Hare Psychopathic Checklist: screening version (PCL: SV) and NEO Five Factors Inventory (NEO-FFI). The results were analyzed with Pearson correlation coefficient, regression, and t-test for the independent group. Results showed positive and significant correlation between psychopathy with extraversion and also negative and significant correlation between psychopathy with openness, agreeableness and conscientiousness. The comparison of psychopath prisoners with non-psychopath and non-prisoners showed that there were significant differences between groups in conscientiousness, agreeableness, openness; thus psychopath prisoner, in comparison with other groups, was lower in conscientiousness, agreeableness and openness. More research regarding the studied variables can render brighter data.