Hugh Hefner (7/30) List item Submitted to "30 Celebrities That Served in The Military" Approved by Ed Hugh Hefner served in the military from 1944 – 1946. While enlisted, Hefner served as an Infantry Clerk, and during Basic Training, he won a Sharpshooter Badge. MoreReport Item navigation Previous submission Next submission View full list See more Previous article Jimi Hendrix (7/30) Next article Mr. T (7/30)