Anna Wintour on Film: 9 Ways to Go Behind the Scenes of the 'Vogue' Editor-in-Chief's World

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Known for her trademark pageboy bob and dark Chanel sunglasses,
Anna Wintour has a signature look that has often served as armor, hiding her
emotions from the cameras and press that often follow one of the most powerful
women in media. Yet, ever since Wintour’s former assistant, Lauren Weisberger,
wrote the 2003 best-selling roman a clef, The
Devil Wears Prada
, the longtime Vogue
editor-in-chief and artistic director of Conde Nast has been taking off the
glasses -- and letting audiences peek inside her world.

She is more than “the dragon lady,” as she was described in
the book (and later in the 2006 film starring Meryl Streep and Anne Hathaway),
and The First Monday in May, which
opens the 2016 Tribeca Film Festival, is the latest film to expose the many
sides of Wintour. 

The First Monday in May (2016) 

Directed by Andrew Rossi, the new documentary focuses on one
of Wintour’s biggest legacies outside of Vogue:
the Costume Institute Gala. Also known as the Met Ball, the annual fundraiser
benefiting the Metropolitan Museum of Art’s Costume Institute in New York City
has become a major social event since Wintour became chair in 1995. The film looks
specifically at planning 2015’s event, China:
Through the Looking Glass
, which saw Wintour and museum curator Andrew
Bolton navigating cultural sensitivities and trying to secure Rihanna as the
event’s marquee entertainment.

Highlight: Seeing
Wintour implore Rihanna to lower her performance fee and make sure she stays on
brand with the event’s theme.

The Fashion Fund (2016)

Now in its third season (the first two aired on Hulu and
Ovation TV), the Amazon reality series follows 10 designers vying to be named Designer
of the Year by the CFDA/Vogue Fashion
Fund competition. However, the real draw is seeing Wintour and members of the
board -- designer Diane von Furstenberg and J. Crew president Jenna Lyons --
discuss the merits of each designer. The show itself is less of a Project Runway-inspired reality
competition and more of a look behind the process of awarding a legitimate
fashion prize.

Watching Wintour chastise Furstenberg for her unbiased comments during a panel
interview and complaining about the applicants’ repetitive videos.

73 Questions…(2014)

While this is technically a web series, 73 Questions has become a viral hit for Vogue with Victoria Beckham, Nicole Kidman and Iggy Azalea all
answering a list of seemingly random questions -- 73 to be exact -- from Joe
Sabia, digital artist and Head of Development at Conde Nast Entertainment. Over
the course of five and a half minutes, Wintour shares whom she wants to play
tennis doubles with and her least favorite word in fashion.

Highlight: Watching
the growing disdain on Wintour’s face as she participates in her magazine’s own
web series.

and I
(2014), The Last Impresario (2013), In Vogue: The Editor's Eye (2012), Venus
and Serena
(2012), Bill Cunningham New York (2010)

Following The
September Issue
(see below), Wintour embraced her life as a talking head
and fixture among various fashion documentaries. While these stories don’t get
into her life, they do offer a glimmer of appreciation she has for the world
surrounding her. “We all get dressed for Bill,” she famously told director Richard
Press in the 2010 documentary about the New
York Times

Highlight: Aside
from her now-famous quote about Cunningham, seeing which documentaries she
appears in with or without her trademark shades. 

The September Issue (2009)

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The most famous look into Wintour’s world has to be this 2009
documentary about the making of Vogue’s
largest, annual issue. The film, directed by R.J. Cutler, is part of a
zeitgeist moment for Wintour that followed in the wake of The Devil Wears Prada. It offers a look at her role as
editor-in-chief and navigating the big personalities of her staff (creative
director Grace Coddington and editor-at-large Andre Leon Talley) and even
bigger expectations that weigh heavily on Wintour.

Watching the symbiotic relationship between Wintour and Coddington unfold as
they battle over photo shoots and layouts in the September issue.

Watch a clip from The First Monday in May, which will hit select theaters on Friday, April 15.