Caution: Today's story contains content intended for an adult audience; viewer discretion is advised. From Naomi Campbell indulging in a milk bath to a voyeuristic threesome a la Helmut Newton, the new iPlayboy app invites readers to take a digital, x-rated walk down memory lane. The brand has enlisted the likes of hotelier André Balazs, fashion designer Jeremy Scott, author Simon Doonan, jewelry designer Waris Ahluwalia, fashion duo Vena Cava, filmmaker David Gordon Green and creative directors Partners & Spade for their Playboy Commission; each has picked their favorite moments in the brand’s extensive archive. The selection spans the magazine’s 1953 debut, which featured Marilyn Monroe on its cover, to its recent 689th issue, and includes saucy pictorials starring everyone from Drew Barrymore to Ursula Andress. “The idea is to give people another way to view the material—through the eyes of the cultural and fashion elite, the people who are leaders in their field,” explains Playboy’s editorial director, Jimmy Jellinek. Below, we asked the experts to annotate the above selections.
 
Jeremy Scott on Naomi Campbell by David LaChapelle, December 1999
David LaChapelle's photos of Naomi were so exciting to me, especially as they were in Playboy! That was the cherry on top, as it would be something we could expect to see in a fashion magazine. The photo of Naomi with the milk was a brand new concept for a girlie magazine centerfold.

Vena Cava on the March 1960 Cover
This is an amazing image: a cross between a movie still and an art piece, and ever so slightly out of focus.

Patrick Grant on “Here’s Looking at You” by Helmut Newton, January 1991 
Newton was 70 years old when he took these pictures. His output had reduced considerably but his reputation was stronger than ever. This has all of the sumptuous mise-en-scène that was his signature.

Waris Ahluwalia on the May 1959 Cover
I believe in cleanliness ... in groups.

Partners & Spade on Miss April, April 1967
It's the hair and the matching argyle outfit and socks. It would make any Scottish-Asian proud.

Vena Cava on “The Lass Menagerie,” December 1965
There are some weird nude spreads in this era and this is one of my favorites—specifically the naked "giraffe". It’s like a pornographic children's book.

Jeremy Scott on Nastassja Kinski by Helmut Newton, May 1983
The images Helmut Newton took of Nastassja Kinski were mesmerizing, as the elements do not all add up to make complete sense. Why the Marlene Dietrich doll? And the pool?

Vena Cava on the May 1988 Cover
I love the idea of a pornographic magazine that just has eyes and lips on the cover: far sexier than your typical T&A.

André Balazs on “Designs for Living,” July 1961
George Nelson, Edward Wormley, Eero Saarinen, Harry Bertoia, Charles Eames and Jens Risom. These guys completely transformed what any of us have in our pads today. Chair designers all, it shows that getting this one thing right is the key to the success of every designed environment, and why mid-century is here to stay.

Simon Doonan on the September 1957 cover

Every copy of Playboy is an orgy of groovy visuals. To flip the pages is to experience an orgasm of chic typefaces, gutsy illustration, hip copywriting, top-notch photography and thoughtful, mind-expanding prose. The Playboy aesthetic of the Madmen-style, pre-feminist 60s resonates the most for me. It's a world of nylons, cigarette lighters, cone-bras and sports cars.

David Gordon Green on Miss January, January 1993
In the fall of 1993, I remember packing up the Playboy issue featuring Miss January, Echo Johnson, and bringing her images along with me to my freshman year at the University of Texas at Austin. She served me well that year, kept me company, and set a young man’s new standard for beauty.

The Playboy Commission launches July 14 and is available to download from iplayboy.com