Sexual sadism and psychopathy have been theoretically, clinically, and empirically linked to violence. Although both constructs are linked to predatory violence, few studies have sought to explore the covariation of the two constructs, and even fewer have sought to conceptualize the similarities of violence prediction in each. The current study considered all four Psychopathy Checklist-Revised (PCL-R) facets and employed well-defined, validated measures of sadism to elucidate the relation between sadism and psychopathy, as well as to determine the role of each in the prediction of non-sexual violence and sexual crime behaviors. Study 1 assessed 314 adult, male sex offenders using archival ratings, as well as the self-report Multidimensional Inventory of Development, Sex, and Aggression (the MIDSA). Study 2 used archival ratings to assess 599 adult, male sex offenders. Exploratory and confirmatory factor analyses of crime scene descriptions yielded four sexual crime behavior factors: Violence, Physical Control, Sexual Behavior, and Paraphilic. Sadism and psychopathy covaried, but were not coextensive; sadism correlated with Total PCL-R, Facet 1, and Facet 4 scores. The constructs predicted all non-sexual violence measures, but predicted different sexual crime behavior factors. The PCL-R facets collectively predicted the Violence and Paraphilic factors, whereas sadism only predicted the Violence factor. Aggr. Behav. 40:12–23, 2014. © 2013 Wiley Periodicals, Inc.