Ever wonder what actually goes down when the most famous people on the planet huddle in a room where the floral arrangements cost more than a suburban house? I'm talking about that specific brand of chaos found in the 2016 documentary by Andrew Rossi. The cast of The First Monday in May isn't just a list of names on a call sheet; it’s a collision of high-stakes museum curation and the kind of celebrity ego that makes for incredible television. Honestly, watching Andrew Bolton try to explain the "art" of a dress while Anna Wintour worries about whether a pillar is blocking a view is the kind of drama you can't script.
The film follows the lead-up to the 2015 Met Gala and the "China: Through the Looking Glass" exhibition. It’s a wild ride. You've got the Vogue team on one side and the Metropolitan Museum of Art’s Costume Institute on the other. It's basically a war of nerves disguised as a party.
The Power Players: Who Really Ran the Show
When people talk about the cast of The First Monday in May, they usually start with Anna Wintour. She’s the sun that everyone else orbits. In the doc, she’s exactly what you expect—decisive, slightly terrifying, and obsessed with the seating chart. There’s this great scene where she’s basically trying to move museum architecture because it doesn't fit her vision for the dinner.
Then there is Andrew Bolton. He’s the heart of the film. While Anna is the face of the gala, Bolton is the guy in the basement actually steaming the gowns. He's the Chief Curator of the Costume Institute, and you can see the literal weight of the world on his shoulders. He was trying to follow up the massive success of the Alexander McQueen "Savage Beauty" show, which is a lot of pressure for one human being.
The dynamic between them is fascinating. It’s not just boss and employee; it’s two perfectionists trying to merge two very different worlds.
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The Supporting Architects
- Sylvana Ward Durrett: As the Director of Special Projects at Vogue, she’s the one actually dealing with the logistics. If Rihanna needs a specific stage or the budget is spiraling, Sylvana is in the line of fire.
- Wong Kar-wai: The legendary Hong Kong filmmaker served as the exhibition’s artistic director. He’s the one who had to tell Bolton that putting Mao suits in a room full of Buddhas was a terrible idea.
- Baz Luhrmann: He pops up as a creative consultant, bringing that "Great Gatsby" energy to the planning sessions.
The Celebrity Cameos You Forgot Were There
The cast of The First Monday in May is basically a Who’s Who of 2015 pop culture. It’s like a time capsule. You see Rihanna in that iconic yellow Guo Pei gown that launched a thousand "omelet" memes. The film actually shows the struggle of getting her through the door in that thing. It was massive.
Then there’s the "blink and you’ll miss it" moments with people like Justin Bieber, who is seen admiring a Maoist uniform and asking his entourage how it would look on him. Kinda surreal, right? George Clooney and Amal Clooney show up looking effortlessly perfect, while Jennifer Lawrence is caught being, well, Jennifer Lawrence—kicking off her shoes and walking up the stairs in a way that makes you realize even A-listers get tired of heels.
You also catch glimpses of:
- Lady Gaga
- Beyoncé
- Kanye West and Kim Kardashian
- Robert Pattinson
- Anne Hathaway
It’s not all glamour, though. Larry David shows up and looks exactly as confused by the whole spectacle as you might expect. He basically asks "What the f*** is this?" which is honestly the most relatable moment in the entire movie.
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Why the "Cast" Matters for Fashion History
The documentary isn't just about famous people in pretty clothes. It’s about the debate over whether fashion is actually art. The cast of The First Monday in May includes heavy hitters from the design world like Karl Lagerfeld, Jean Paul Gaultier, and John Galliano.
Lagerfeld is particularly interesting here. He’s a bit of a contrarian. Despite being a titan of the industry, he’s seen questioning whether his own work should even be in a museum. He’s got this "it’s just a dress" attitude that clashes perfectly with Bolton’s "this is a masterpiece" vibe.
Gaultier, on the other hand, is like a kid in a candy store. Watching him walk through the finished exhibit is one of the few times the film feels genuinely joyous rather than stressed. He sees the craft. He sees the history.
The Conflict Nobody Talks About
One of the tensest parts of the film involves the museum's Department of Asian Art. They weren't exactly thrilled about a "fashion show" taking over their sacred galleries. The cast of The First Monday in May includes curators who were genuinely worried that the bright lights and pop music of the gala would demean the ancient Chinese artifacts.
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There's this guy, Maxwell Hearn, who is the head of the Asian Art department. He’s the "fuddy-duddy" foil to Bolton’s modern vision. The movie frames it as a clash between the old guard and the new, but if you look closer, it’s a real conversation about cultural sensitivity. They even go to Beijing to meet the press, and it’s awkward. The Chinese journalists ask why the exhibit focuses on Western fantasies of China rather than real Chinese history.
It’s a valid question that the film doesn't quite answer, but seeing Wintour and Bolton try to navigate that minefield is compelling.
Actionable Insights for Fashion Documentary Fans
If you're looking to dive deeper into this world or just want to understand why this specific cast of The First Monday in May remains so influential, here is what you should do next:
- Watch "The September Issue" first: It’s the spiritual predecessor to this film and gives you the necessary backstory on Anna Wintour’s leadership style.
- Research Guo Pei: The designer of Rihanna's yellow dress became a global sensation after this film. Her work is a bridge between traditional Chinese craft and modern haute couture.
- Look up the 2015 "China: Through the Looking Glass" catalog: If you want to see the "cast" of garments (the 140+ pieces mentioned in the film), the catalog has the high-res photos the documentary moves past too quickly.
- Check the Met's current exhibition schedule: Andrew Bolton is still there. He’s still the one deciding what the world considers "fashion art" every year.
The real takeaway from the cast of The First Monday in May is that nothing this big happens without a massive amount of friction. It takes a village of designers, curators, celebrities, and one very determined woman with a bob to pull off the "Super Bowl of fashion." It’s messy, it’s expensive, and honestly, it’s kind of ridiculous—but that’s exactly why we can’t stop watching.