Andrew Rossi On Anna Wintour and His Met Gala Documentary The First Monday in May

The film, which opens the Tribeca Film Festival tonight, offers an inside look at the party of the year, and a new perspective on the woman behind it.


When Andrew Rossi was approached to direct The First Monday in May, a documentary about the making of the Met Ball which opens the Tribeca Film Festival tonight, he admitted he was a little nervous to meet Anna Wintour, the woman behind the party of the year and, of course, Vogue‘s Editor-in-Chief and Condé Nast’s Artistic Director. But luckily, he left the initial meeting feeling that “she was a warm person who would be great to follow,” he recalled. And follow her he did—through her home, office, and the Metropolitan Museum of Art, from the fall of 2014 until May of the following year, when “China: Through the Looking Glass” opened at the Costume Institute. The result is an inside look at how both Vogue and the Met pull off such a colossal event, told through the dual narratives of Wintour and Andrew Bolton, the curator of the Costume Institute and “kind of the hero of the film,” according to Rossi. Here, the director talks making fashion into film, attending the Met Ball, and working with Wintour.

How did you get involved in working with Vogue and the Costume Institute? I was contacted by [Vogue Director of Special Projects] Sylvana Ward Durrett, to meet with her and then with Anna Wintour about creating a film that would showcase what the Met’s Costume Institute does. [The goal was] to understand more deeply the importance of fashion and the power of fashion, and also of course to capture the Met Gala, which I think is an event that a lot of people in the fashion world know about but have never really seen inside. And so the question was, “If Anna and the Met pull back the curtain, is there a story to be found there?” And I certainly thought there was. I was particularly excited at the ability to go behind these great institutions and understand them more deeply through the journeys of individuals that comprise them. Andrew Bolton, the curator at the Met in charge of the Costume Institute, is kind of the hero of the film.

Had you been interested in fashion prior to working on this film? Yes, absolutely. One of the movies that was most formative to me in becoming a documentary filmmaker was Unzipped, which I saw in theaters back in 1995. I think that Unzipped is such a gorgeous, lush, intimate story of one person’s creative process. It’s incredibly fun and funny, and Isaac Mizrahi is a great character. As a filmmaker, I really enjoy tackling a diverse range of topics, so I’ve made pieces that are investigative documentaries about higher education and students, more verité-style stories, including Page One, which is about David Carr, the former columnist at the New York Times who recently passed away. The fashion documentary is a great stalwart, a great genre of the medium. I was thrilled to take it on.

It seems like the making of the Met Gala is a good story to tell because there are a lot of different components to work with. I’m drawn to stories that are driven by the kind of characters that one can’t look away from. But on the other hand, I’m also really interested in making movies that deal with ideas that I can unpack, and that are not shy about being intellectual and analytical. In this case, for me, it was a perfect marriage of a character-driven story, because we’re able to follow what Anna does, and Anna is this icon of pop culture and certainly a figure who many people want to watch and don’t look away from. But the context of the Costume Institute and the Metropolitan Museum also gives a framework for us to look at these important questions about the aesthetics of fashion and the sociological role that fashion plays in our culture. So hopefully it will operate on a lot of different levels.

What was it like working with Anna Wintour? I think her mythology precedes her, and I was a little bit trepidatious when I went in to meet her. I left feeling really excited and that she was a warm person who would be great to follow. There were certain moments when she was under one kind of obligation or another that I wasn’t able to film, and she’s not shy about communicating that. So if she didn’t want to film she would tell me very clearly. But that was good, and it was a healthy shoot. She let me film at her house several times, which I think adds to the intimacy of the portrait of her. And she’s also not 100 percent of the movie. It’s sort of a dual narrative structure, I think in some ways similarly to The September Issue [2009], which looks at Anna Wintour and Grace Coddington. Here, you have Anna Wintour and Andrew Bolton.

Anna and Grace were pitted against each other as creative opposites in The September Issue. Was that the case with her and Andrew? That’s one of the things that contributes to what I believe is a different perspective on Anna, because she’s working so much in partnership with Andrew Bolton, or in a supporting role to him because she’s an advocate for the Costume Institute. She’s there to help him; she’s not there to edit him. And she’s also really personally invested in the mission of the Costume Institute and her work as a trustee of the Metropolitan Museum of Art. So we see a side of her I think that is different from what we’ve seen in the past.

During filming, did you learn anything about fashion that surprised you? Just understanding more how art and commerce come together at the Costume Institute, and the Met Gala. The Met Gala is so crucial to providing the funds for the Costume Institute. That was in many ways a revelation just because it’s such a spectacular context to see that in. And to understand how celebrity and high fashion come together, and how the sum of their parts is bigger than each one of them individually.

What did you think of the Met Ball, just as an observer? As an observer I thought it looked like a really fun party. It almost has the feeling of a reunion or something because you have a lot of people in entertainment who have worked together or know each other in one way or another. So you see Madonna talking to Kanye West and Kim Kardashian in the corner. And they’re talking about, you know, “Thank you for sending the flowers,” or, “I’m in the studio, blah blah blah.” There’s that camaraderie that seems very personal and yet everyone has a sense of, “Wow, look who that person is in that corner of the room.” So it feels like this great equalizer.

What do you hope audiences take away from the film? One of my favorite scenes in the film is at the very end when we see Andrew Bolton walking through the galleries where the exhibition, “China: Through the Looking Glass,” has been staged. And everyone is enjoying the party and he’s just with these mannequins and these costumes. You go through this journey with him and Anna Wintour, understanding the stress of putting on a show, putting on a party, inviting certain people, making the trains come in on time. And at the end you’re just left with these beautiful clothes, which hopefully you’ve come to understand more deeply as art. I hope people come away with a certain visual joy.

Photos: Andrew Rossi On Anna Wintour and His Met Gala Documentary The First Monday in May

A scene from “The First Monday in May.” Photo courtesy of Magnolia Pictures.

Andrew Bolton in “The First Monday in May.” Photo courtesy of Magnolia Pictures.

Andrew Bolton in “The First Monday in May.” Photo courtesy of Magnolia Pictures.

A scene from “The First Monday in May.” Photo courtesy of Magnolia Pictures.

Anna Wintour, Andrew Bolton, and Wendi Deng in “The First Monday in May.” Photo courtesy of Magnolia Pictures.

Andrew Rossi. Photo courtesy of Magnolia Pictures.

Photo courtesy of Magnolia Pictures.