Vanity Fair’s yearly Hollywood Issue requires months of preparation and coordination. It’s an annual advanced exercise in star-scheduling, high-fashion logistics, and photographic prowess. This stuff is for the pros, kids. So imagine our surprise a few months back when Joe Evangelisti, head of worldwide corporate communications for JPMorgan Chase, sent us what looked like group portraits from Hollywood Issues past but were, somehow, awry. In fact, they were re-creations of all-female V.F. cover portraits—posed by stripped-down, muscled men. Investigating the provenance of these gender-bending works of art, we discovered that many were the product of lavish get-togethers hosted by a wealthy entrepreneur, who prefers to remain anonymous, in exotic locales, which culminated in photo shoots of his buffest, if not his best, friends.

The photo shoots are informal, staged quickly and shot on an iPhone. In the beginning, the crew would create covers of a motley mix of famous photos, but after a few years they “graduated to Vanity Fair,” says the group’s self-proclaimed spokesperson, L.A.-based photo agent Jorge Perez.

Evidently, throughout the vacations, nobody can stop thinking, Which girl do I get to be? “Everybody’s gunning for the best position,” explains Perez. “Nobody wants to be sitting.”

For instance, on one getaway, a certain model was adamant that he should be Naomi Watts as she appeared on the 2004 issue. That he was ultimately denied the role is perhaps shocking, considering that he was Watts’s personal trainer. But “guys would be cast based on body types . . . how quickly they jumped on the role, and seniority in the group travel,” explains A-list celebrity colorist, and crew member, George Papanikolas. One model got so intensely into the role of Gwyneth Paltrow that he insisted on being her again in the next photo shoot. His request was approved, for with his striking, meditative stare, he was a sublime Gwyneth.

Even though slackers risked being demoted, it’s clear from the shots that certain guys were less devoted to their roles than others. Some obvious minor adjustments, like facing the same direction the celebrity faced in the original, would have made a few of these re-creations much more recognizable as such. In that vein, a onetime prominent Nicole Kidman got recast as a seated starlet. “And he was really upset about it,” recalls Perez.

In the end, each model is happy to take advantage of the opportunity to “show that you can blend campiness and masculinity,” says Perez. We are told the campy cohort includes a film director, a venture capitalist, a porn producer, and a banker.

“Everyone in the group has such different lives,” says Papanikolas, “and those trips really bring the best out of everyone.”

For future V.F. re-creations, follow @jorgeperezjr on Instagram. Or make your own—have you checked out the 2016 Hollywood Issue?—and send it to letters@vf.com.