Willingham attended Jacksonville Senior High School in Jacksonville, North Carolina and lettered in football, basketball, and baseball.[citation needed] He went on to Michigan State University where he played football and baseball and graduated in 1977 with a degree in physical education. Willingham held assistant coaching positions at his alma mater (1977, 1980–82), Central Michigan University (1978–79), North Carolina State University (1983–85), Rice University (1986–88), and Stanford University (1989–91). When Stanford head coach, Dennis Green, was hired as the Minnesota Vikings head coach in 1992, Willingham followed him as running backs coach (1992–94).