The famous Vanity Fair photo shoot began a controversy that really ushered in the beginning of Miley's adoration for the inappropriate. Miley was just 15 years old when she posed seemingly half-naked for Annie Leibovitz for Vanity Fair in 2008. However, we can't lay the blame for all of this on Miley since there were several other adults (including her father, Billy Ray Cyrus) involved with the shoot. While it might not be the worst thing she's ever done, she was still famous for being Hannah Montana and it seemed widely inappropriate for her millions of pre-teen fans to see her in such a scandalous photo.