This article describes how counselors may use the portrayal of a historical character in the classroom to teach lessons on self-esteem, motivation, and goal setting. Keeping with a creative spirit, a classroom guidance lesson that involves the use of character portrayal can be engaging for students. This involves the counselor assuming the personality and physical characteristics of a positive role model from history and teaching a lesson to the students on the subjects of motivation, goal setting, and how to overcome obstacles. Entitling the program "Teddy Roosevelt's America," the author taught a lesson dressed in character to all fourth- and fifth-grade students at his school, which involved a costume, props, music, and a computer presentation. The article will provide the reader with background as to the efficacy of role models with children, as well as the action steps for creating the lesson. School counselors often find the need to use a wide variety of resources and creative ways to keep the attention span of children during classroom guidance. Appendix A contains an excerpt from the script of the lesson. Appendix B is a pre-test on Theodore Roosevelt.