The aim of the study was to explore the ways in which a Series of Creative Structured Activities (SCSA) involving humor elements, affected the type and quantity of visual and verbal productions of two preschoolers. Researchers agree on the incongruity element of humor (Theory of the Absurd) and violation of expectations (Empowerment Theory). Also, creativity in relation to humor was examined through fluency, flexibility, originality and elaboration (Torrance test). Data collection included children's humorous drawings and stories, before and after participating in a SCSA and were analysed based on the two theories and the creativity elements. The SCSA affected positively the quantity and originality of humorous events produced by the two children in their drawings and stories. We highlight that the use of a SCSA provides a safe space for children to explore new ideas playfully and creatively; unfold their humorous self and scaffold their creative thinking.