It's hard to think of a more challenging test for realistic illustration than Vladimir Nabokov's book, Lolita. Nabokov emphasized to his publisher that any illustrator who attempted a representational image of the character would be missing the point. He wrote: "There is one subject which I am emphatically opposed to: any kind of representation of a little girl."
The difficulty of illustrating Lolita has been widely recognized. The (excellent) book, Lolita; The Story of a Cover Girl contains essays and dozens of images on "Vladimir Nabokov's novel in art and design." Lit Hub compiled a (useless) survey, The 60 Best and Worst International Covers of Lolita and here are 210 covers over the years. In 2016 The Folio Society produced what they called the First-Ever Illustrated Version of Vladimir Nabokov’s Lolita."
Many artists and art editors have tried coming up with realistic illustrations for Nabokov's psychologically complex novel but the results have been pretty worthless:
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Illustration for the recent Folio edition
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You may not think much of the talents of these particular illustrators, but replace them in your imagination with your favorite representational illustrator. Is there a facial expression or a pose or a color scheme that you think would be more successful?
Now contrast the representational images above with the conceptual illustrations below, often using photography or graphics.
In my view, these conceptual illustrations are far more impressive; they get closer to the meaning of the book; they engage the viewer and inspire deeper thought. The sheet of notebook paper shockingly reminding us of what a 12 year old girl is. The broken lollipop or the crumpled clean white page conveying besmirched innocence. The repetitive writing of Lolita's name giving us insight into Humbert Humbert's obsessive brain.
The following photographic illustration (one of my favorites in this series) could be the view of the deranged Humbert lying in bed staring at the ceiling, and it could also be the panties of a 12 year old girl. A very powerful use of imagery by Jamie Keenan.
Could this image have been as effective if it was painted by a talented artist? I doubt it. Crimped by the intent of the artist, a painting would look too much like either panties or a ceiling. The objectivity of the camera gives this image its double entendre, and it gives us the shock when we realize what our mind is seeing.
If anyone can suggest more effective representational paintings or drawings of this book, I would welcome them. Absent that, I think these images are strong evidence for the argument that the end justifies the means in illustration, and that excellence can extend beyond hand drawn or painted images, to encompass some kinds of photography, graphics and digital imagery.