The ability to express emotion is considered a core socioemotional skill; however, most research is focused on receptive abilities, with little investigation of productive abilities. We present an investigation of individual differences in facial expression of emotion using observational techniques. Given descriptions of highly psychopathic persons as successful liars and manipulators, we investigate the ability to intentionally pose emotional expressions when no emotion is elicited. A mixed sample of adult men (N = 316 community volunteers, prison inmates, and forensic-psychiatric patients) ranging along the psychopathy continuum were asked to facially express a nonfelt emotion, specifically anger, disgust, fear, happiness, sadness, and surprise, through either written instructions or through imitation of a target's facial expression. Through structural equation modeling, we evaluate relations between this emotion expression ability and general mental ability, interpersonal abilities, and psychopathy. We find that psychopathy is moderately associated with poorer emotion expression ability, meaning highly psychopathic individuals are poorer at imitating the expressions of others and poorer at expressing all emotions. However, this deficit is largely attributable to deficits in general mental ability. These results challenge the view that highly psychopathic individuals have the cognitive skills to support a superior ability to deceive or manipulate others. (PsycInfo Database Record (c) 2021 APA, all rights reserved).