Miley Cyrus Reflects on ‘Really Brilliant Choices’ of Topless 2008 ‘Vanity Fair’ Cover

In the spirit of her new single “Used to Be Young,” Miley Cyrus is strolling down memory lane and reflecting on some of the most pivotal and controversial moments of her nearly two-decade career. For Part 15 of her Used to Be Young TikTok series, Cyrus tackled her controversial 2008 Vanity Fair photo shoot.

Fifteen years ago, Cyrus posed for the cover of Vanity Fair. The shoot was helmed by famed photographer Annie Leibovitz, and featured a then-15-year-old Cyrus exposing her bare back to the camera as she wrapped her body in what appeared to be a sheet. At the time, Cryus was still starring as the titular character on Disney’s blockbuster television series Hannah Montana. The Vanity Fair shoot was intended to help further differentiate Cyrus from the character that quickly consumed her.

Upon release, Miley disregarded the potential controversy of the image saying at the time, “I mean I had a big blanket on. And I thought, ‘This looks pretty and really natural.’ I think it’s really artsy.” Nonetheless, controversy inevitably ensued, forcing Cyrus, Leibovitz and Disney to release statements apologizing for the photographs. In the years that followed, the controversy continued to obfuscate the real story and intent behind the images, “which is always much more meaningful,” according to Cyrus in her new TikTok post.

She 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.”

What the star calls “really brilliant choices” made in an effort to separate Miley Cyrus from Hannah Montana, the public perceived as the inappropriate hypersexualization of America’s most beloved and recognizable child star.

Cyrus’ initial apology, which she retracted via Twitter (now known as X) a decade later, read, “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.” For its statement, Disney went for an offensive approach, writing, “Unfortunately, as the article suggests, a situation was created to deliberately manipulate a 15-year-old in order to sell magazines.”

As for Leibovitz, she defended her work. “I’m sorry that my portrait of Miley has been misinterpreted,” she said. “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 makeup, and I think it is very beautiful.”

Check out Part 15 of Miley Cyrus’ Used to Be Young TikTok series:

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