The smoking jacket. The grotto. Working in bed with a Pepsi and a pipe. You already know all this about our founder. But most are not familiar with his sketch-y past.

Hef’s been cartooning practically since he was old enough to hold a pencil. Growing up in Chicago with a genius IQ but mediocre grades, Hef founded his high school paper, where he both wrote and cartooned. After graduating, he joined the Army in 1944 and drew for it’s various newspapers while serving as an infantry clerk. With the end of World War II and his discharge, he took classes at the Art Institute of Chicago—in anatomy—before enrolling at the University of Illinois in Urbana/Champaign. There, he drew cartoons for the Daily Illini and edited the campus humor magazine Shaft, where he also contributed cartoons.

Playboy would come 4 years later, but these were his formative—and figurative—years. As he told the Los Angeles Times in 2009, “I…did comic books in grade school and high school. I actually started a comic-book autobiography in high school called School Daze about the adventures of my friends and myself. The comic book was a way of creating your own world and being center stage. And only years later did I realize that when I started the magazine, and the way I used the magazine in my life, it had a direct parallel to what I did in high school. The comic book became the scrapbook that I have continued then throughout my life and now has over 2,000 volumes.”

Those volumes include work from the mighty pens of illustrators Gahan Wilson, Jules Feiffer, and Shel Silverstein, who joined the Playboy staff in 1956 and stayed for 40 years. And of course frequent references to Playboy’s ultimate super hero: Batman.