We evaluated the differential effects of employment status on chronic pain and healthy comparison groups. Forty unemployed and 43 employed individuals with chronic pain, as well as 43 unemployed and 45 employed healthy comparison participants completed a series of measures assessing background information, physical and psychological adjustment, and psychosocial features of employment status. In general, participants experiencing both chronic pain and unemployment reported poorer adjustment than the other groups and more financial strain, less structured and purposeful activity, fewer opportunities for skill use and task variety, and decreased social support than the employed chronic pain and healthy comparison groups. Groups did not differ, however, in work ethic values. Scores on measures of pain severity and features of employment status accurately predicted the group membership of more than 70% of respondents from the four groups. The study suggests that there is utility in understanding experiences of chronic pain patients on the basis of features of their current employment status and points to a need for multidimensional measures that evaluate psychosocial facets of employment and unemployment specifically for chronic pain samples.