I am curious about when was the first time (novel, tale, paint, drawing, etc.) that the iconic human skull/raven motif was used to refer to the Master of the Macabre, Edgar Allan Poe?

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    Quoth the raven, probably on a book cover; gohd.com.sg/wp-content/uploads/2015/04/… although he was sat upon an bust of Pallas – Valorum Oct 19 '19 at 16:39
  • Is this a question about science fiction or fantasy? – Laurel Oct 19 '19 at 16:48
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    @Laurel - It's about the history of an icon associated with a fantasy author; "Behind-the-scenes and fandom information" – Valorum Oct 19 '19 at 18:17

The image of something raven-like (an hour glass with raven's wings, as a symbol of Death) on a skull certainly goes back a long way. Gottfried Wilhelm Sacer made a woodcut of the image in the middle to late 1600s:

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As for Poe, certainly the illustrations of Carling and Doré (in specific, those for The Raven) of the mid-late 19th century at least place the raven properly on the bust of Pallas, if not an actual skull.

I think this is one of Carling's creepier ones:

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Doré's version:

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Most of the raven on skull imagery I'm finding appears rather newer, so perhaps not quite the answer you're looking for!

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