While doing ethnographic fieldwork in a school for high school dropouts in a city in southern Sweden, a lively, often ironic, joking culture between teachers and students was observed, resulting in the following research question: What purposes can joking serve in a school setting for students who have lost faith in their own ability to perform in school? The findings suggest that jokes can support the mobilization of individual cognitive capabilities and that they could function as a kind of pedagogical practice to help students manage, in a more collective way, the double consciousness created by belonging to low-status immigrant groups. The article also sheds light on the question of whether we can understand humor in a high school dropout context as something other than an indicator of a counter-school culture. In dialogue with Paul Willis’s seminal work Learning to labor (1977), the article offers a new understanding of embodied counter-school cultural practices. Instead of a counter-school culture solely acted out by students, there may exist a counter-counter-school culture that is performed by teachers, where students’ cultural practices become resources that are taken over and used by teachers. In comparison with Willis’s results, the present findings show that joking is not always about reproduction in a school context, but that it can bring teachers and students closer to each other in non-conformist ways, in this way allowing conformist spaces to open up for the students.