Miley Cyrus Looks Back at Infamous 'Vanity Fair' Topless Pic: 'Everyone Knows the Controversy'

The singer recalled her scrutinized 2008 photoshoot while taking a deep dive into her past for her new "Used to Be Young" TikTok series

Miley Cyrus Looks Back at Infamous Vanity Fair Topless Pic: ‘Everyone Knows the Controversy’
Miley Cyrus dives into her past in new "Used to Be Young" TikTok series. Photo:

Miley Cyrus TikTok

Miley Cyrus is not holding back.

The star has been “sharing untold stories” from her past as part of her “Used to Be Young” series on TikTok, telling fans the truth behind some of the infamous moments. And on Wednesday's installment, Cyrus, 30, dissected her 2008 Vanity Fair photoshoot, which featured her posing topless.

“We gotta go there,” she said as she began the 40-second video, where she described some of the background that went into the creation of the iconic shot. 

“Everyone knows the controversy of the photo but they don’t really know the behind-the-scenes, which is always much more meaningful,” Cyrus said. “My little sister, Noah, was sitting on Annie [Leibovitz]'s lap and actually pushing the button of the camera, taking the pictures. My family was on set.”

One of the standout memories she has from the shoot, though, has nothing to do with her pose — or her lack of a top. “This was the first time I ever wore red lipstick,” she shared, adding, “Because Patti Dubroff, who did my makeup, thought that that would be another element that would divide me from Hannah Montana.”

Miley Cyrus Looks Back at Infamous Vanity Fair Topless Pic: ‘Everyone Knows the Controversy’
Miley Cyrus reflects on her infamous 2008 Vanity Fair photoshoot in new installment of her "Used To Be Young" series on TikTok.

Miley Cyrus TikTok

Reflecting on why the photo caused such public outrage, Cyrus said it was all rooted in the image that the role of Disney Channel's Hannah Montana had created, which the photoshoot was a clear step away from.

“This image of me is a complete opposite of the bubblegum pop star that I had been known for being and that’s what was so upsetting.”

“But — really brilliant choices, looking back now, from those people,” she added of Leibovitz, Dubroff and others’ stylistic choices.

When the Vanity Fair photos were released, Cyrus faced intense scrutiny.

A New York Post headline, “Miley’s Shame,” blasted the then 15-year-old and what it called a “near-nude pic.” 

“Here’s wholesome ‘Hannah Montana’ as you never expected to see her,” the Post’s front page story began. 

In 2018, Cyrus revisited the photo — and the scrutiny she faced for it — as she tweeted “I'M NOT SORRY” and shared a photo of the Post front page from a decade before. “F--- YOU #10yearsago.”

Miley Cyrus Looks Back at Infamous Vanity Fair Topless Pic: ‘Everyone Knows the Controversy’
Miley Cyrus slams New York Post's 2008 front page in tweet from 2018.

Miley Cyrus Twitter

In a statement shared with PEOPLE shortly after the photos were released, the “Flowers” singer said she was “honored and thrilled to be working with” Leibovitz, but wasn’t happy with the outcome.

“I took part in a photo shoot that was supposed to be ‘artistic’ and now, seeing the photographs and reading the story, I feel so embarrassed,” the statement said.

She added that the photos were “silly, inappropriate shots.”

In its own statement, Disney Channel, which was home to Cyrus’ hit show, Hannah Montana, said: “Unfortunately, as the article suggests, a situation was created to deliberately manipulate a 15-year-old in order to sell magazines.”

Miley Cyrus Sheds Tears and Reflects on Her Partying Days in Emotional New 'Used to Be Young' Music Video
Miley Cyrus poses for her new single, "Used To Be Young".

NOUA UNU Studio

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Cyrus has been sharing clips on TikTok as part of her “Used to Be Young” series all week. The series, which celebrates the release of her song of the same name, sees her “start at the beginning” of her story in 1992 and trace the course of her three decades of life. 

“Sometimes it feels like my life started when Hannah Montana was born,” Cyrus wrote in an Instagram post. “But before Hannah there was Miley. My fantasy was to light up the world with laughter, music & iconic moments that last beyond my lifetime. Decades later I continue to fulfill my purpose because of the love provided by my fans."

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