By Susan Toepfer/Executive Editor
Updated May 10, 1999 12:00 PM

When you set out to photograph the 50 Most Beautiful People in the World, you’re bound to encounter a few surprises. This year, none was bigger than comedian Jon Stewart’s agreement to pose on the condition that he could do it in a prom dress—for a couple of shots, anyway.

“Forty-nine people are doing the right thing,” said the host of Comedy Central’s The Daily Show. “I want to do something different.” Jumping at the chance to be seen as he has never (he assures us) been seen before, he wedged himself into a $1,500 vintage dotted tulle frock and, with tiara, gloves and beaded cashmere sweater in place, declared, “I feel pretty.”

Our plans to shoot Britney Spears took an unexpected turn when the 17-year-old pop phenom hurt her knee while rehearsing for a video and had to undergo arthroscopic surgery. Photographer Sandra Johnson, scrapping her original scenario of a dancing Spears, kept a chair and ice pack at the ready. Spears was “in a lot of pain, and it wasn’t easy for her to get in and out of her clothes,” reports Johnson, “but she didn’t complain once.”

By comparison, shooting our cover picture of Michelle Pfeiffer—who makes a record sixth appearance as a Beauty—was uneventful. “She’s just as beautiful now as she was the first time,” says photo editor Maddy Miller, who has supervised the images for 8 of the 10 Beauty issues we’ve produced to date. “She works the camera with her eyes.”

Still, this shoot involved a remarkable coincidence. In 1990, Pfeiffer lit up the cover of our first collection of 50 Most Beautiful People, while inside, a 20-year-old commercial artist from Nashville, Norman Jean Roy, appeared in a feature on real-life lookers, “Beauty on Your Block.” Now an established celebrity photographer, Roy took this year’s pictures of Pfeiffer. “It was full circle,” he marvels.

Maybe so, but in the years since that first issue, we’ve weathered plenty of trends. “Hairstyles and clothing are always evolving. One year, everyone wanted to wear black. This year’s colors were brighter,” reports Miller, who adds, “but skin is always in.”

We’ve also made a few editorial refinements along the way. “Unless there’s a reason, we no longer reveal how much our beauties weigh, and we’ve grown more interested in beauties of all ages,” says senior editor Elizabeth Sporkin. What hasn’t changed, though, is the issue’s popularity, Sporkin notes, partly because “readers want to see how their choices compare to ours.” No surprise there.