In this paper, a parallel analysis of the enjoyment derived from humor and insight problem solving is presented with reference to a “general” Theory of the Pleasures of the Mind (TPM) (Kubovy, 1999) rather than to “local” theories regarding what makes humor and insight problem solving enjoyable. The similarity of these two cognitive activities has already been discussed in previous literature in terms of the cognitive mechanisms which underpin getting a joke or having an insight experience in a problem solving task. The paper explores whether we can learn something new about the similarities and differences between humor and problem solving by means of an investigation of what makes them pleasurable. In the first part of the paper, the framework for this joint analysis is set. Two descriptive studies are then presented in which the participants were asked to report on their experiences relating to solving visuo-spatial insight problems (Study 1) or understanding cartoons (Study 2) in terms of whether they were enjoyable or otherwise. In both studies, the responses were analyzed with reference to a set of categories inspired by the TPM. The results of Study 1 demonstrate that finding the solution to a problem is associated with a positive evaluation, and the most frequent explanations for this were reported as being Curiosity, Virtuosity and Violation of expectations. The results of Study 2 suggest that understanding a joke (Joy of verification) and being surprised by it (Feeling of surprise) were two essential conditions: when they were not present, the cartoons were perceived as not enjoyable. However, this was not enough to explain the motivations for the choice of the most enjoyable cartoons. Recognizing a Violation of expectations and experiencing a Diminishment in the cleverness or awareness initially attributed to the characters in the cartoon were the aspects which were most frequently indicated by the participants to explain why they enjoyed the joke. These findings are evaluated in the final discussion, together with their limitations and potential future developments.