Miley Cyrus Looks Back at Her Controversial Topless ‘Vanity Fair’ Photo Shoot From 2008

Miley Cyrus is looking back at the defining moments of her career in her Used to Be Young TikTok series, and she’s tackling some of the biggest controversial moments of her life.

One such moment was the heated outcry sparked by her 2008 Vanity Fair cover, shot by Annie Leibovitz. In the latest installment of her Used to Be Young series, the 30-year-old singer reflects on how hard she worked to separate herself from her cookie-cutter image that came with starring in Disney Channel’s hit show, Hannah Montana, from 2006 to 2011. In Part 15 of the TikTok series, Cyrus notes that many people remember the controversy that the photo set off, but they don’t know the sentiment that took place behind the scenes “which is always much more meaningful.”

Cyrus recalls, “My little sister, Noah, was sitting on Annie’s lap and actually pushing the button of the camera, taking the pictures. My family was on set, and this was the first time I ever wore red lipstick, because Pati Dubroff, who did my makeup, thought that that would be another element that would divide me from Hannah Montana.”

“This image of me is [the] complete opposite of the bubblegum pop star that I had been known for being,” the singer notes. “And that’s what was so upsetting. But really, really brilliant choices looking back now from those people.”

The Leibovitz photo chosen for the Vanity Fair cover featured the then 15-year-old Disney star’s bare back exposed with her body wrapped in a satin sheet. 

When the image originally came out in the Vanity Fair piece — titled “Miley Knows Best” — Cyrus brushed it off, saying, “I mean I had a big blanket on. And I thought, ‘This looks pretty and really natural.’ I think it’s really artsy.”

Shortly after the image was released, Cyrus issued a statement, apologizing for posing in such a manner. “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,” she said at the time. “I never intended for any of this to happen and I apologize to my fans who I care so deeply about.”

In response to backlash from the media, parents and others, Disney issued a statement, saying, “Unfortunately, as the article suggests, a situation was created to deliberately manipulate a 15-year-old in order to sell magazines.”

At the time Leibovitz also released a statement on the subject, saying, “I’m sorry that my portrait of Miley has been misinterpreted. Miley and I looked at fashion photographs together, and we discussed the picture in that context before we shot it. The photograph is a simple, classic portrait, shot with very little make-up, and I think it is very beautiful.”

Ten years later, Cyrus would retract her apology. On April 29, 2018, the then-25-year-old “Malibu” singer shared an old New York Post cover on X (formerly known as Twitter).

The image, which featured the 2008 Vanity Fair photo, had the headline, “Miley’s Shame: TV’s ‘Hannah’ apologizes for near-nude pic.”

Cyrus tweeted the image, writing, “I’M NOT SORRY F**K YOU #10yearsago.”

The Used to Be Young series accompanies the release of Cyrus’ latest single of the same name. In the emotional music video for the song, the singer opens up about the highs and lows of her past. 

Cyrus released the song’s lyrics in full earlier this week and shared what inspired her to pen the track. “These lyrics were written almost 2 years ago at the beginning of my ESV,” she wrote of Endless Summer Vacation, the album she released back in March. “It was at a time I felt misunderstood. I have spent the last 18 months painting a sonic picture of my perspective to share with you. The time has arrived to release a song that I could perfect forever.”

“Although my work is done, this song will continue to write itself everyday,” she continued. “The fact it remains unfinished is a part of its beauty. That is my life at this moment ….. unfinished yet complete. Sincerely, Miley.”

The Used to Be Young TikTok series currently has 19 videos for fans to watch. In one, Cyrus opens up about her home in Malibu, California, that she shared with ex-husband Liam Hemsworth. Cyrus said that while writing her first solo album, Meet Miley Cyrus, she was introduced to the residence, and it was where she recorded the songs. 

She didn’t know that 15 years later, it would become a major part of her life.

“That house had so much magic to it,” the “Used to Young” singer added. “It ended up really changing my life.”

Cyrus and Hemsworth, 33, lived in the Malibu home until the Woosley wildfires destroyed it in 2018. At the time, Cyrus was away filming, and Hemsworth was at their house and rescued a number of their pets. A rep for the then-couple told ET that the duo donated funds that would aid in rebuilding and preventing more fires from overcoming the area.

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