Humor is applied in pedagogy to create a positive learning environment. Recent research focuses on the theories, effects, individual differences, and qualitative aspects of humor for instruction. However, there is a lack of studies focusing on quantitative features. Therefore, this research explored the quantitative characteristics of instructional humor in a naturalistic setting and applied techniques from natural language processing (NLP). This paper describes the results of two studies. The first study focused on instructional humor frequency and the placement of humor, while the linguistic features of instructional humor and non-instructional humor were compared in the second study. Two corpora were used in this research: TED Talks and user-submitted jokes from “stupidstuff.org” The results found that educators used humor 12.92 times for popular talks, while less popular talks only had 3.92 times. Humor is also more commonly placed during the first parts of the talk and lessens toward the end. There were also significant differences between the linguistic features of instructional and non-instructional humor in terms of readability scores and sentiment. These results provide a substantial update on quantitative instructional humor research and help educators understand how to use humor in the classroom in terms of quantitative and linguistic features.