A new documentary about the influential figure in fashion, Anna Wintour, is set to air on CNN. Entitled *Behind the Bob: Vogue’s Anna Wintour*, this special feature will be available on May 3, one day ahead of the highly anticipated Met Gala. Wintour, renowned for her pivotal role in shaping modern fashion and media, has been closely associated with the Met Gala since she began serving as co-chair in 1995 and subsequently became the sole chair in 1999.
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The documentary delves into Wintour’s extensive influence and examines her nearly three-decade reign within the fashion industry. It promises to present both her substantial achievements and the various controversies that have accompanied her career. This glimpse into Wintour’s life and legacy is timely, coinciding with the build-up to the 2026 Met Gala, an event that has become a cornerstone of the fashion calendar.
Initially founded in 1948 by fashion publicist Eleanor Lambert, the Met Gala, or The Costume Institute Benefit, began as a modest fundraising dinner among New York’s elite for the Metropolitan Museum of Art’s annual exhibits. Over the years, it has transformed into a high-profile celebration of fashion, attracting a diverse range of celebrities from various fields including film, music, sports, and politics. Under Wintour’s guidance, the event has evolved from a mere charity gala into a worldwide cultural spectacle that garners significant media attention.
The documentary not only tells Wintour’s story but also highlights her instrumental role in elevating the Met Gala to its current status. Since the introduction of themed dress codes in 1973, the event has generated numerous memorable and sometimes contentious fashion statements, with designers and their celebrity guests creatively interpreting the chosen theme.
*Behind the Bob* features interviews with several prominent figures from the fashion industry, including designers Isaac Mizrahi and Melitta Baumeister, as well as journalists such as Michael Grynbaum. Former colleagues from Vogue, including Tonne Goodman, Sally Singer, Stephanie Winston Wolkoff, and William Norwich, are also expected to lend insight into Wintour’s professional life. Their contributions offer a multifaceted perspective on Wintour’s influence and the narrative surrounding her career.
As anticipation builds for this year’s Met Gala, the dress code has been announced as “Fashion Is Art,” which will connect to the exhibit titled “Costume Art.” The event is set to feature a star-studded roster of co-chairs, including music icon Beyoncé, actress Nicole Kidman, and tennis champion Venus Williams. With Wintour at the helm, the gala is poised to be another remarkable celebration of creativity and fashion.
*Behind the Bob: Vogue’s Anna Wintour* will be broadcast on May 3 at 8 p.m. ET on CNN and is currently available for streaming on CNN’s digital platforms for subscribers. The documentary promises to be a compelling tribute to Wintour’s enduring impact on fashion, media, and cultural events. As the fashion world eagerly awaits the 2026 Met Gala, this documentary serves as an essential prelude to a night that celebrates the artistry and innovation that define contemporary fashion.
In summary, Anna Wintour’s journey and the evolution of the Met Gala are interwoven tales of influence, creativity, and ambition. Through this documentary, audiences will gain a deeper understanding of the woman behind the legendary bob hairstyle and her lasting legacy in the realm of fashion.