When fellow knockout Paulina Porizkova appeared on the pages and the cover of the August 1987 Playboy, supermodel Cindy Crawford became an overnight fan of the “Entertainment for Men” magazine. “I was suddenly buying Playboy to see Paulina,” she says, laughing, “but I never imagined that I’d actually do a layout in it one day. But then I saw what Herb Ritts did with Brigitte Nielsen in the December issue. And I thought, Wow, if he can make her look that good, I’d love to see what he could do with me. That’s when I decided to go for it.”

The shoot would take place along the sands of Kona and Kanapala, Hawaii—a backdrop perfectly suited to Cindy’s volcanic sensuousness. Although the sessions lasted only three days, both the photographer and the model recall that they required equal measures of stamina and stimulation. The decision to shoot in black and white seemed as natural as Cindy herself; the results, long before they reached our Chicago office, promised to be memorable. “Even before I saw one Polaroid from the shoot,” says Cindy, “I knew it would turn out to be special. We put a ton of energy into this thing—going at it all day—yet it wasn’t torture, by any stretch of the imagination. After all,” she says, smiling, “it’s not unenjoyable trying to make beautiful pictures. And Herb knows how to do that.” The pictorial appeared in the July 1988 issue.

Herb Ritts died in 2002 after spending a lifetime photographing some of the world’s most beautiful women in a signature style that made them even more memorable. His work is larger than life, a reflection of the man and his remarkable talent.