1. Cindy Crawford as George Washington

  2. Drew Barrymore as Marilyn Monroe

  3. Barbara Streisand as Betsy Ross

  4. Demi Moore

  5. Harrison Ford as Abraham Lincoln

  6. Robert De Niro as George Washington (with Washington’s real sword)

  7. Julia Roberts as Susan B Anthony

  8. Karen Mulder

  9. Salma Hayek

  10. The Farewell Issue

by nizaad

15 Comments

  1. I can’t be the only one that had to double and then triple check that the first pic wasn’t Rachel Zegler. …right? ….right????

  2. VirusHeavy1280 on

    That whole series feels like someone put “90s Vanity Fair” and “8th grade history class” in a blender and hit purée. The De Niro as Washington one lives rent free in my head, it’s so serious and so goofy at the same time. Also Julia Roberts as Susan B Anthony is such a hilariously specific choice, like who pitched that with a straight face 😂

  3. ImAboiledCabbage on

    So weird I was just thinking about the Cindy Crawford cover a few days ago without ever mentioning it. It was such an iconic cover when I was a kid.

  4. frolicndetour on

    I had a subscription to this mag. I actually liked it…I think in some ways it was ahead of its time about the confluence of pop culture and politics. Back then, there are not as many celebs who were as vocal about politics, especially without having social media to platform it.

  5. He did a Marilyn cover?? The woman who had an affair with his father and humiliated his mom in front of the nation with that flirtatious birthday song? Wow.

  6. Educational-Help-126 on

    I’ve been weirded out by the commentary on this man and Carolyn recently. The biggest ick that I’ve experienced has been the think pieces about how innovative JFK Jr was with his personal style. He clearly styled himself with black men as the inspiration. His magazine was ahead of its time but it is comical how he never included his inspiration on the covers.

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