Annie Leibovitz shot the first pics of Bruce Jenner's amazing transition for the upcoming issue of Vanity Fair, a publication known for its ground-breaking, jaw-hits-the-floor photography.

This is hardly the first time Leibovitz and crew have shocked the newsstands. Here, six of the most controversial VF covers to date.

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Bruce Jenner becomes Caitlin, July 2015

After months of speculation, the former Olympic athlete and reality TV star reveals her new stunning new identity in a lush Annie Leibovitz photo shoot. All we can say is: Bravo!

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Demi Moore, August 1991

Seven months pregnant and totally au naturel, Demi graces the VF cover.

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K.D. Lang and Cindy Crawford, August 1993

It seems tame now, but then, Lang had just come out as a lesbian and everyone was abuzz.

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Miley Cyrus, October 2013

In 2013, Italian Vanity Fair published an old photo of a 15-year-old Miley Cyrus...practically in the nude. Fans were shocked. (Little did they know, she'd be swinging naked from a wrecking ball in just a few years' time.)

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Tom Ford, Scarlett Johanson, Kiera Knightley, March 2006

After Rachel McAdams ducked out of this cover photoshoot due to concerns about baring it all, Ford stepped in to balance the composition.

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Tiger Woods, February 2010

The shirtless golfer graced the VF cover two months post-infidelity confession and golf club/car crash catastrophe. No more Mr. Nice Guy.

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