With the participation of eleventh graders at the Affiliated Senior High School of National Kaohsiung Normal University, this study used various research methods (including classroom observations and document analysis) to explore the effects and value of applying creative concepts of Pop Art into senior high school art teaching. The results show that the multicultural phenomena represented by post modernism in contemporary art created a mosaic combination of different eras, societies, and cultures to students and provided them with refreshing and energetic experiences. Additionally, features of Pop Art such as popular culture seemed more attached to the students’ subcultures. Through the teacher’s guidance, the transformation of visual images, and the application of multimedia materials, students extended their aesthetic experiences into their creation. They also demonstrated their abilities in both aesthetic creation and appreciation. Based on these learning experiences, students may be able to rebuild their inner life order to formulate their future living prospects. Finally, this study provided suggestions to overcome the challenges of teaching contemporary art in high schools, presented feasible teaching models, and provided insight into the education of art.