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So, on the chat room just now we were discussing how classic pictures would be improved by adding in the Iconics. Which seemed somewhat amusing, and hey, if any of you artists wanted to make something like this up, it'd be pretty ace to see. Anyway, the pictures we thought up were this.
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Merisiel and Ezren in the American Gothic picture by Grant Wood.
The Last Supper, with all the Iconics. (Though who gets to be Jesus is up for debate!)
Abbey Road, with Valeros, Seoni, Merisiel and Kyra.
Birth of Venus by Botticelli, with Seoni as Venus.
Any other fun suggestions from you guys?

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Guess Gustav Courbet isn't as well known as I expected. I was sure we'd have every possible permutation for L'Origine du monde and Le Sommeil by now. I'll suggest Lem for Self Portrait (aka The Desperate Man).
Seltyiel, Valeros, Kyra, and Sajan (L to R) for Nighthawks, Edward Hopper. Seoni and the LoF early employer for his Chop Suey.
Amiri for The Charging Chasseur, Gericualt.
Ezren as Sadko in Ilya Repin's Sadko in the Underwater Kingdom.

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Difficulty:
/cast all iconics
/no repeating artwork from other posters
/no repated artists within my own posts
Lini and Droogami in Rousseau's The Sleeping Gypsy
Ezren in Blake's Ancient of Days
Merisiel in Waterhouse's Miranda - The Tempest
Seelah in Moreau's St. George and the Dragon
Lem in Gainsborough's The Blue Boy
Kyra in Goya's The Naked Maja
Seoni in Collier's Lady Godiva
Seltyiel in Munch's The Scream
Will have to do Valeros, Harsk, Sajan, and Amiri later...