Insight problem-solving training is a core topic in creativity education and creative thinking. However, few studies on enhancing such skills have identified the norms of insight problem-solving. According to the literature, a commonality exists between insight problems and jokes. Therefore, the purpose of this study was to investigate insight problem-solving rules and examine their effects on improving problem-solving skills and divergent thinking through analyzing the problem-solving characteristics and structures of jokes. In the first study phase, 101 participants were randomly assigned to either the insight problem-solving training group or the control group. The experimental group received training for “homonyms,” “exceptions to the rules for punch lines,” and “alternatives for punch lines,” and completed tests on insight problem-solving skills and divergent thinking. The results indicated that the experimental group had significantly better performance in “homonyms,” “alternatives for punch lines,” and overall insight problem-solving than the control group. In the second study phase, differences in the effects of three types of insight problem-solving training were examined. A total of 200 college students were recruited and randomly assigned to four groups: “homonyms,” “exceptions to the rules for punch lines,” “alternatives for punch lines,” and “no training” (i.e., the control group). The results indicated that the “homonyms” group performed significantly better for “homonyms” and overall insight problem-solving than the other groups. However, training for “exceptions to the rules for punch lines” and “alternatives for punch lines” exhibited no significant effects insight problem-solving and provided preliminary findings for the effects of training of “homonyms” derived from the structure of jokes. These findings could be applied in practice for future insight problem-solving skill training courses.