The goal of the current study was to assess the interrater reliability of the Psychopathy Checklist—Revised (PCL–R) among a large sample of trained raters (N = 280). All raters completed PCL–R training at some point between 1989 and 2012 and subsequently provided complete coding for the same 6 practice cases. Overall, 3 major conclusions can be drawn from the results: (a) reliability of individual PCL–R items largely fell below any appropriate standards while the estimates for Total PCL–R scores and factor scores were good (but not excellent); (b) the cases representing individuals with high psychopathy scores showed better reliability than did the cases of individuals in the moderate to low PCL–R score range; and (c) there was a high degree of variability among raters; however, rater specific differences had no consistent effect on scoring the PCL–R. Therefore, despite low reliability estimates for individual items, Total scores and factor scores can be reliably scored among trained raters. We temper these conclusions by noting that scoring standardized videotaped case studies does not allow the rater to interact directly with the offender. Real-world PCL–R assessments typically involve a face-to-face interview and much more extensive collateral information. We offer recommendations for new web-based training procedures.