Calvin Klein muse Josie Borain, considered South Africa’s first supermodel, shared a light-hearted story behind this candid photograph of her and Jean-Michel (photo #1), taken in New York City in 1986. “I played doorman/woman at one of Bruce Weber’s book launches, this guy (Basquiat) wasn’t on the list, but I let him in anyway. Hahaha.” Josie soon became a friend of Jean-Michel’s, and managed to photograph him on a few more occasions in what was developing into Josie’s distinct photojournalistic style. Josie went on to become a professional photographer, and in 2003 released her book, “Josie, You, and Me,” chronicling her travels and experiences in the modeling industry. All photos by Josie Borain.