Not many people know that Hef wanted to be a cartoonist growing up, which led to many a great cartoonist getting gigs for Playboy. Jane Sellers, a best-friend of Hef, saved all his old cartoons:

At 16, I knew he was destined to do amazing things, so I saved every scrap of paper he ever sent or gave me

Hef himself:

“ I was most interested in writing and cartooning….I wrote short stories and lots of mysteries and horror stories and 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. I then began adding clippings and photographs too. It eventually became like a scrapbook.

Link totally SFW, by the way.

Photo of Maggie Gyllenhaal on set by Jeff Bridges

Makeup reference photo of Vivienne Leigh

Is there anything sexier than a blonde and a book?

Cartoonists + models in bathing suits = happy plewds.

(via THE BEAT)

Another Eve Arnold shot of Marilyn reading Ulysses

His drawings from his seventies often contrast himself as a buffoonish, wizened dwarf opposite a beautiful young woman.

Jonathan Richman and the Modern Lovers said it best:

Well some people try to pick up girls
And get called assholes
This never happened to Pablo Picasso
He could walk down your street
And girls could not resist his stare and
So Pablo Picasso was never called an asshole

(…)

Well he was only 5’3”
But girls could not resist his stare
Pablo Picasso never got called an asshole

In Joyce and Popular Culture, R.B. Kershner quotes a letter from Arnold about the day she took the shot:

We worked on a beach on Long Island…I asked her what she was reading when I went to pick her up (I was trying to get an idea of how she spent her time). She she kept Ulysses in her car and had been reading it for a long time. She said she loved the sound of it and would read it aloud to herself to try to make sense of it–but she found it hard going. She couldn’t read it consecutively. When we stopped at a local playground to photograph she got out the book and started to read while I loaded the film. So, of course, I photographed her.