Little research has examined the aggregation of humor expression among adolescents. The purposes of this study were to understand the natural clusters of types of humor expression among youth in Taiwan and to discover any related background factors that may shape these aggregations of humor styles. A nationwide survey was conducted of 1,639 students in the seventh to ninth grades. Participating junior high schools were randomly selected in Taiwan. Cluster analysis was used to explore types of humor expression. Multinomial logistic regression modeling was used to examine factors related to types of humor expression. The sample was divided into four clusters based on humor expression and personality: (a) frequent use of various humor types (16.1%); (b) used of deprecating humor group (26.7%); (c) non-hurtful witty group (22.4%); and (d) serious or austere (or rarely use of humor) group (34.9%). Individual (e.g., grade, birth order, academic performance, perceived stress and allergy-related problems) and family factors (e.g., mother’s education, parent’s marital status and family income) were related to clusters of humor expression. Our study discovered that different aggregations of humor expressions exist among youth and that significant associations exist between different background factors and the natural clusters. Based on our study results, we recommend early contact with junior high school students to help establish positive ways that they can express their humor during this crucial period of time. Such insights may very well lead to educational programs or coursework that can enhance students’ understanding of the proper use of humor and its overall role in society.