Engaging fully with contemporary art requires analysis of the relationship between creative imagination, personal experience, and cultural context. This article discusses the study of contemporary works of art as an effective tool for fostering the development of critical thinking skills in a freshman writing class at an art college. In a carefully structured progression of written assignments, students are guided in the step-by-step exploration of the work of three specific artists and their writings. Close attention is paid to students’ written responses to assignments to illustrate how close engagement with the work of specific contemporary artists is particularly well-suited to the development of students’ skills in critical thinking and writing.