Psychopaths have long been associated with a unique ability to manipulate others (Hare, 1999). To shed more light on language production in psychopathy two studies of language production were performed comparing content and fluency under different motivational and difficulty conditions. It was observed that individuals high in psychopathy (HP) were less fluent but maintained a more complex lexicon, than their low psychopathy counterparts, when under high cognitive load and low motivation. Yet when the HP individuals were under low cognitive load and high motivation, they were more fluent, but produced less complex lexicon. Furthermore, it was found that the HP group produced more emotional language in both conditions. The results suggest that HP individuals’ linguistic abilities are inherently related to motivation. Results are discussed in terms of Theory of Mind and emotion perception processes.