1926 Hugh Marston Hefner is born in Chicago on April 9 to Protestant parents Glenn and Grace Hefner. Ironically, Hef's a direct descendent of Massachusetts Puritan patriarchs William Bradford and John Winthrop.

1940-1944 Hugh attends Steinmetz High on the West Side of Chicago where he founds a school paper, draws cartoons and serves as president of the student council. He adopts the nickname "Hef."

1944-1946 Hef joins the Army, serving as an infantry clerk and drawing cartoons for various Army newspapers.

1946 Hef spends the summer taking art classes (anatomy, of course) at the Chicago Art Institute.

1946-1948 Hef earns his bachelor's degree from the University of Illinois at Champaign/Urbana in two-and-a-half years by doubling up on classes. He also draws cartoons for the Daily Illini and edits the campus humor magazine Shaft, in which he introduces a feature called "Coed of the Month."

1949 Hef takes a semester of graduate courses in sociology at Northwestern University where he writes a term paper examining U.S. sex laws in light of the newly published Kinsey Institute research on male human sexuality.

1949 Hef takes a job as an assistant personnel manager for the Chicago Carton Company, earning $45 a week. Hef weds Northwestern classmate Mildred Williams. Their marriage lasts for ten years.