Fife played basketball and football for Clarkston High School in Clarkston, Michigan. In basketball, he was coached by his father, Dan Fife. After his senior season in 1998, he was named Mr. Basketball of Michigan over runner-up Antonio Gates, and was also named a McDonald's All-American and Parade All-American. A blue-chip recruit in basketball and also a star quarterback, Fife was recruited to play both sports in college. He ultimately committed to play basketball for Indiana under head coach Bob Knight. He chose Indiana over Duke, Michigan State, and Michigan, where his father had played baseball and his older brother Dugan had played basketball. Fife became a vocal supporter of Knight, and nearly transferred from the team to Michigan State following the coach's firing in 2000.