Professor Rockland served as a corpsman in the US Navy during the Cold War in the mid-1950s, including service in Naval Hospital Yokosuka in a psychiatric unit. He served in the US Information Agency from 1961 to 1968, with postings in Argentina and Spain. He served as Executive Assistant to the NJ Chancellor of Higher Education from 1968 to 1969. He came to Rutgers University in 1969, first as an Assistant Dean at Douglass College (1969-72), then as a Professor of American Studies (1972-present), serving as chair of American Studies from 1972 to 2000.