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The First Monday in May opened the Tribeca Film Festival last week. It's about the making of the Metropolitan Museum of Art's star-studded annual Met Ball, the glitzy fundraising gala for the Costume Institute that opens its spring fashion exhibition, and confirms that Hollywood's romance with fashion – and the event's chair Anna Wintour – continues apace. Lately, however, it's doing so for worse more often than for better.

Here, filmmaker Andrew Rossi (Page One: Inside the New York Times) is granted exclusive behind-the-scenes access to the making of last year's exhibition, China: Through the Looking Glass, and over months, follows the show's inception and ensuing labours of Wintour, guest artistic director Wong Kar-Wai and curator Andrew Bolton. The documentary is a sequel of sorts to The September Issue, which was filmed during the 20th-anniversary year of Wintour's position as editor-in-chief of Vogue. The breakout star of the movie, however, was her friend and foil Grace Coddington, the magazine's creative director. The First Monday in May, similarly, was filmed in what was Wintour's 20th year orchestrating the Costume Institute gala. It's a process and panic countdown, peppered with ridiculously over-the-top moments, with the result being something like an episode of Ab Fab directed by Frederick Wiseman.

In the movie, people occasionally ask whether fashion can be art and disagree on the answer. But, the bigger question here is whether fashion documentaries can be art – especially since so many seem to be manicured hand-in-glove promotional exercises.

Take the bought-and-paid-for feel of director Matthew Miele's Scatter My Ashes at Bergdorf's, a fawning film only recently bested by his follow-up Crazy About Tiffany's. It's one of those "documentaries" where the audience can't tell the difference between what's cooperation and what's a commercial, maybe because the director can't either. By Miele's own admission, his Quixotic Endeavours production company works only on official "fully authorized" stories of iconic institutions and themes that have "built-in target audiences," which sounds more like a business plan than an artistic statement.

This latest one gloms both its name and raison d'être from a line of Audrey Hepburn's dialogue in Breakfast At Tiffany's – the one she enthusiastically delivers as she pours herself a champagne coupe of milk, while wearing a robin's-egg blue sleep mask. It's all-access gush that is so comprehensive as to be incoherent; it leaves out no aspect of Tiffany's reach or history. No aspect, that is, except an interview with Elsa Peretti, the most iconic of Tiffany's long-time designers. Peretti is discussed by the parade of employees and friends of the luxury brand and shown in archival photos but her conspicuous absence from the film is never broached. (Theirs is a contentious relationship.)

The First Monday in May does not treat its subject with kid gloves and goes to pains to show the project's frequent necessary exercises in diplomacy – with potential guests, between the Met's disparate departments, unveiling the fraught theme to indignant Chinese press – and ongoing discussions over cultural appropriation.

This kind of access combined with trust (where subjects cede creative control) tends to make for better films. The September Issue, wherein R.J. Cutler insisted on creative control and final approval, and director Matt Tyrnauer's Valentino: The Last Emperor are other examples. Tyrnauer's talking point was that while he and the crew may have, over time, become part of Valentino's extended fashion house family, that didn't prevent him from exercising the final cut stipulation in his contract. (Valentino was initially displeased with the film – until it became a popular hit and cemented his iconic status.)

Fashion, however, is an industry more prone to coziness than most, and brands have an expectation of – and regularly exert – control over how they are represented in seemingly objective editorial. Magazine subjects are often big advertisers who can't be offended; if editorial spreads have a boring sameness, it's because many designers only lend out samples of key seasonal looks on the condition that the outfits are photographed as shown on runway, in what's known as the "total look."

There's nothing inherently wrong with the impulse to celebrate. Many good documentaries are born of equal parts intrigue and admiration, like the biographical documentary about the Costume Institute's first doyenne Diana Vreeland made by granddaughter-in-law Lisa Immordino Vreeland (who never met her famous subject). Journalistturned– filmmaker Janice Zolf recently made an independently funded documentary about designer Marie Saint Pierre and, to do so, secured her subject's cooperation but kept her distance. "We remained at arms' length throughout," Zolf explains of Revealing, which will soon air on CBC's DocChannel and in May on Air Canada. "You don't want to be influenced by the person that you're interviewing."

An offending guests's name in The First Monday in May may be blurred out at Wintour's request, but director Rossi otherwise makes no deal with the devil. As the film's cunning editor, he observes a Miranda Priestly moment when an off-screen assistant hands a coffee to her boss, who breezes by, and a glimpse of the powerhouse fleetingly choked up at the Met ribbon-cutting with Michelle Obama unveiling the Costume Centre newly renamed in her honour. In an instance of sobering visual commentary, Rossie foregrounds workers carving foam away from the already-tiny waists of exhibition mannequins.

While the proceedings are sometimes unkind and reveal unflattering aspects of the process, they're seldom off message. Forget separation of church and state: The film was produced by the newish entertainment division of Vogue's parent company. The division's stated goals? "To leverage Condé Nast's iconic portfolio of brands." The First Monday in May cements Brand Anna, the sphinx-like star of the film. And her mythology is not only cemented, it gets the biggest laughs.

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