“I’ve never understood why everybody likes them so much,” the photographer David Bailey once said of fashion’s obsession with Jean Shrimpton and Kate Moss. Of course, that might be because Bailey was already close with both (and dated Shrimpton for four years, before marrying, for a time, Catherine Deneuve). And, unlike many on the seemingly endless list of celebrities that the now 79-year-old, nostalgia-averse Bailey has gotten in-your-face close with in his now nearly six decades of photographing, he’s still close with Moss to this day. So when the team behind the biannual magazine Humanity tapped Bailey to guest-edit their latest issue and asked him to “make it personal,” he put Moss on the cover. Bailey, being the unconventional and ungovernable spirit he is, though, bent the rules and enlisted his buddy Ronnie Wood of the Rolling Stones, aka “the Peter Pan of the pop world,” to simultaneously paint his own portrait of Kate. Both of their versions (one on film, one on canvas) can be found alongside the rest of Bailey’s closest London friends—including London mayor Sadiq Khan, who while often the butt of Bailey’s playful political teasing, still contributed an essay; and of course Bailey’s longtime pal, the artist Damien Hirst. Oh, and there’s also so much of Bailey’s actual family, from his children to his wife Catherine, that “we look like the f—ing mafia,” as he said with a laugh. Take an exclusive look inside the issue, here.