A previously ignored method of assessing relative levels of alienation is the content analysis of work jokes exchanged in different venues. This study uses quantitative content analysis to code 1,085 joke-texts collected from ten job-sites and from the Internet. Using past measurements of powerlessness, meaninglessness, social isolation, and self-estrangement, the author develops a content protocol that is consistent with popular alienation indexes. Past methods for assessing both the functions of humor and the concept of alienation are criticized as tautologies, and null-categories for the social-psychological aspects of alienation (empowerment, understanding, social integration, and self-actualization) are introduced and critically examined. Research expectations are developed, and evaluations of predictions are made by comparing the proportion of jokes between the data sets within each of the conceptual categories. Jokes posted to the Internet are found to have more expressions of alienation in each of the social-psychological aspects except meaninglessness, which was slightly higher for entry-level service workers. The study concludes that the content analysis of jokes may prove to be a more direct way of accessing group sentiment than the study of either individual sentiment or the social structure of work.