The results indicate that child molesters hold a diverse criminal history, but have an elevated level of sexual charges and convictions relative to other sexual offender types. This effect was particularly salient in examining the prolific criminal histories of psychopathic child molesters. Offenders with psychopathy were found to be 2.5 times more likely than non-psychopathic offenders to be successful in their applications for conditional release. This trend existed across different offense types, including psychopathic sex offenders. While psychopathic offenders were more likely to have diverse victim types, psychopathic molesters engaged in a particularly high rate of sexual offending, suggesting that risk assessment tools should be tailored to specific offender groups instead of violent or sexual offenders. Research has found psychopathy to be one of the most powerful predictors of both violent and nonviolent criminal recidivism. This study investigated the influence of psychopathy and sex offender subtype on criminal history, probability of being granted conditional release, and performance while on conditional release in a diverse group of violent offenders. It was hypothesized that psychopathic sexual offenders would be associated with relatively prolific violent and sexual offending, a high probability of successful conditional release applications despite past behavior, and poor performance in the community. Information was gathered through a correctional file review of 310 Canadian male Federal offenders. Figures and references