There is an increasing interest in using cross-disciplinary approaches to teaching and learning. More specifically, the authors believe that using West Indian literature to teach educational philosophies can promulgate more open discussions during classroom sessions, enhance students' conceptualization of educational philosophies, and engender more interest in the tenets of these philosophies. Therefore, this paper demonstrates how excerpts from West Indian literature exemplify several tenets from two major educational philosophies, perennialism and progressivism at the tertiary level to Bachelor of Education students. The excerpts from the West Indian novels explored are: Butterfly in the Wind, by Lakshmi Persaud; For The Life of Laetitia by Merle Hodge; Walking by Joanne Haynes; Growing Up Stupid Under the Union Jack by Austin Clarke and Spirits in the Dark by H. Nigel Thomas. Furthermore, this paper suggests ways that these literary excerpts can be used to teach both educational philosophies. The authors hope that using these literary excerpts in teaching these concepts at the tertiary level in the Trinidad and Tobago context can provide the impetus for future research in the domain of education generally and other disciplines.