The main aim of this overview is to discuss theoretical work and empirical studies on the proposed association between humor and playfulness. Starting point is McGhee’s (1996, Health, healing and the amuse system: Humor as survival training. Dubuque, IA: Kendall/Hunt; 1999, The laughter remedy: Health, healing and the amuse system. Dubuque, IA: Kendall/Hunt) notion that humor is a variant of play-the play with ideas. Research on play and playfulness is discussed in light of this proposition and an updated definition of playfulness as a personality trait in adults is presented. The latter differentiates among four facets; namely, Other-directed, Lighthearted, Intellectual, and Whimsical. One methodological problem is highlighted in particular: Items such as “I have a good sense of humor ” are to be found in both, measures for the sense of humor and playfulness and sometimes used as both predictor and criterion in the same analysis. Overall, there is evidence that the proposed overlap between humor and playfulness exists, but that it does not indicate redundancy. Avenues for future research are presented. © 2018 Walter de Gruyter GmbH, Berlin/Boston.