Sleepiness and sleep disorders are increasingly raising interesting and important medical-legal issues in three areas: violent or injurious behavior arising from the sleep period, accidents or errors in judgment caused by sleepiness behind the wheel or in the workplace, and disability determinations caused by sleepiness-induced work impairment. Sleep-related violence may be caused by many conditions, most of which are diagnosable and treatable. Legal issues raised by these behaviors are usually enigmatic. The nature of such behaviors may be extremely complex, and documenting that a given violent act was caused by such a behavior, after the fact, may be difficult. Guidelines for the medical-legal evaluation of such behaviors have been developed and are evolving. Culpability determination in sleepiness- related industrial or motor vehicle accidents is in the developmental stage, and varies by jurisdiction. Disability determination for workplace sleepiness caused by sleep disorders is in its infancy, and poses a challenge, given the erroneous but pervasive societal attitude that sleepiness is a manifestation of laziness, depression, sloth, work-avoidance behavior, or a defect of character.