Who Ditched Her Dress When She Got Inside? Who Mistook the Curator for a Waiter? Met Gala Gossip You'll Love

The stories are almost as great as the gowns

You never imagine the perfectly-coiffed and legendarily cool Anna Wintour putting a single foot wrong, but the longtime host of the Met Gala (and thus, star of the upcoming documentary about it, The First Monday in May) admits that she got caught on camera a couple times doing just that — and sometimes the foot was in her mouth. “People who make documentaries are really sneaky people,” she told PEOPLE at the New York premiere of the film, which opened the Tribeca Film Festival this week. “They just follow you around until you make a complete fool of yourself.”

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But she seems to have a good sense of humor about it — and even admits to getting a little verklempt watching the film. “There is a really moving scene in the documentary which shows Andrew [Bolton, the exhibit’s curator] just before the exhibition opened last year just walking through the empty galleries,” she said. “Yes, to me that was absolutely the most emotional [moment]: When you see his work coming together at the end.”

So is Bolton enjoying his star turn? “Anna’s the star,” Bolton replied modestly. “I think it captures the work that goes into the shows we do, and also the work that goes into the gala. Bolton related that the most amusing encounter he had with a star was his first year at the Met gala when he was introduced to Jennifer Connelly. “She thought I was a waiter and she asked me to go get her a glass of wine,” he said.

So what did he do? “I got it for her,” said Bolton. “And she’s a bad tipper.”

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Designer Zac Posen recalled another unseen moment. “When I brought Christina Ricci for the Alexander McQueen exhibition,” he said. “She was wearing quite an elaborate dress. She had corset trained through the weekend to wear it. But we knew that training would only allow her to wear it up until a certain moment. From having been an intern at the Met, I know the guards there. So they let me go into a back room right after the first course was served, and I change her into a very transparent, short un-corseted dress. And they carried her gown out through the back entrance to the car in a body bag.”

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Supermodel Karolina Kurkova has worn a number of dresses that barely fit in the limo, so much so that she knows exactly how to handle it. “The trick is to sit, and then let someone just shove the dress into the car,” she said. Another highlight every year?“And I have to say the ladies room at the Met is always quite a scene. Everybody is always in there touching up. It will be Jennifer Lopez on one side, and Meryl Streep on the other, Nicole Kidman, Rihanna — that is, if your dress will even fit through the door. At the end of the night, I’ve had to be cut out of a dress many times.”

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Lauren Hutton also described the ladies room as one of the starriest hangouts. “There are some huge dresses,” she agreed. “The Olsens were in there. That’s part of the fun, helping everybody get in and out of their dresses.”

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“I loved Rihanna’s dress last year,” said Wendi Deng, a co-host of the 2015 gala. “It was designed by my friend Guo Pei, a Chinese designer. And I’m so proud of her. She works so hard and is so talented. And it helped put her on the map. I saw her later and we had dinner together and she was so happy about it.”

Andre Leon Tally, another star of the documentary, agreed that the most dramatic moment onscreen was: “When Rihanna came up the steps looking fabulous in the Guo Pei coat,” he said. The dress took two years to create and it required a small army to move and place the enormous train for photos on the stairs out front. Ultimately, it was “a moment in time,” Talley said.

What’s your favorite Met Gala moment?

–Jeffrey Slonim