Hugh Hefner, teenage cartoonist, 1943
Note the conspicuous lack of smut! Frame from a Seattle Post-Intelligencer gallery of Playboy founder hugh Hefner's teenage doodles, sent to his high school
sweetheart friend Jane Sellers in the early 1940s. The full collection is for sale at $250,000, from rare book dealer Lux Mentis (who will send you a PDF listing collection contents upon request).
Update: Ian J. Kahn of Lux Mentis Booksellers tells Boing Boing,
I should point out that Hugh and Jane did not date. He dated her best friend and she his...the four were the core of what they called "The Gang". The really interesting element is that as he evolved into "HH", this group of high school friends served as a touchstone...they were the ones who loved him *before*...and he turned them off and on for many, many years. My favorite story out of this is that Jane and the other girls would go over to Hugh's to read "School Daze" to see which of their boyfriends were "stepping out"...Hugh did not edit *anything*. He took notes during the day as to what people were wearing so he could sketch them accurately that evening. It is a remarkable visual diary.(Via Roger Ebert)