Sometimes, a picture can transform a culture.

Caitlyn Jenner’s Vanity Fair cover, which exploded across the country this week, certainly elicits comparisons with transgender actress Laverne Cox’s 2014 photograph on the cover of Time. Time itself called the photo of Cox a “transgender tipping point,” and, undoubtedly, it paved the way for Jenner to appear on the cover of Vanity Fair.

But Jenner’s photo also evokes a different cover, from a different time. Its existence owes just as much to a pregnant and nude Demi Moore on the cover of Vanity Fair in 1991.

Like Jenner’s cover, Moore’s image was gorgeously and memorably shot by Annie Leibovitz. In both, the women face the camera head-on (even as Moore is turned to show her pregnant belly), and the patina of the print is rich. There’s a barely restrained sexuality in both, even though they are not what the general American public has been trained to perceive as sexy: Moore is pregnant, Jenner is a transgender woman.

Both covers are as controversial as they are iconic, and controversy sells. Moore’s cover helped the magazine shatter sales records. Even though it was considered indecent (it was displayed for sale behind brown paper), it sold more than one million copies (in contrast to a regular distribution at the time of around 800,000).