His family suffered through the Great Depression, "there was never enough money," but Stampp worked a number of small odd jobs as a teen, managing to save enough to afford tuition, first, at Milwaukee State Teachers' College, and then at the University of Wisconsin, Madison. He earned both his B.A. and M.A. there in 1935 and 1936 respectively under the influences of Charles A. Beard (author of "An Economic Interpretation of the Constitution of the United States") and William B. Hesseltine (known for coining the phrase about intellectual history: it's "like nailing jelly to the wall"). Hesseltine supervised Stampp's dissertation; Stampp remembered him as a "bastard" during this time, but the two managed to work together successfully through the completion of Stampp's Ph.D. in 1942. He then spent brief stints at the University of Arkansas and the University of Maryland, College Park, 1942–46, before joining the faculty at Berkeley. His teaching tenure ran 37 years; in 2006, Stampp celebrated "six decades" of association there.