If a picture’s worth a thousand words, imagine what a picture from Vincent van Gogh or Leonardo da Vinci could tell you about your favorite book characters.

No doubt, the master painters could each put their own spin on literature’s giants. But the greatest works of art emerge from a sympathy between the artist and the subject.

These pairings came to my mind:

Peter Pan should be painted by Claude Monet.

Claude Monet is top dog among the impressionists, a camp of artists who believed in dreamy landscapes, vivid colors, and objects in motion. (Can you imagine Peter sitting still for a portrait? Neither can I).

Image result for monet

Above: Imagine Peter soaring by the second star to the right in Monet’s London.

Impressionists were also the first painters to begin working outside, rather than in studios. Why? They wanted to capture natural light. Light, according to the impressionists, is a representation of the transient nature of all things. Light reminds us how constantly and easily the world changes–an appropriate backdrop for a story that begins, “All children, except one, grow up.”

Why Peter and Monet? Monet likes:

  • dreamy landscapes
  • bright colors
  • freezing time

Bilbo Baggins should be painted by Jean-Baptiste Chardin.

Much like Bilbo, Jean-Baptiste Chardin was an unlikely hero in his world. He was a self-taught artist, son of a cabinet maker, and during the height of Paris’s gaudy Rococo period, he chose to paint children, kitchen maids, and blocks of cheese.

File:Jean-Baptiste Siméon Chardin 019.jpg - Wikimedia Commons

Chardin’s love of childhood innocence and (it must be admitted) food would surely have drawn him to hobbits as subject matter for his paintings.

It’s not hard to imagine Chardin standing in for Thorin Oakenshield when he tells Bilbo, There is more in you of good than you know, child of the kindly West. Some courage and some wisdom, blended in measure. If more of us valued food and cheer and song above hoarded gold, it would be a merrier world.

Why Bilbo and Chardin? Chardin likes:

  • childhood innocence
  • unlikely heroes
  • food!

Lolita should be painted by Frida Kahlo. 

Feminist, nationalist, passionate lover and open griever, Frida Kahlo is one of the few artists who could pull off a portrait of Lolita.

There’s a deliberate mania in Kahlo’s paintings that matches Humbert Humbert’s voice when he describes Lolita:

Lolita, light of my life, fire of my loins. My sin, my soul. Lo-lee-ta: the tip of the tongue taking a trip of three steps down the palate to tap, at three, on the teeth. Lo. Lee. Ta. 

She was Lo, plain Lo, in the morning, standing four feet ten in one sock. She was Lola in slacks. She was Dolly at school. She was Dolores on the dotted line. But in my arms she was always Lolita.

Portrait of Miguel N. Lira, 1927 - Frida Kahlo - WikiArt.org

Above: Frida surrounds her subject with objects that represent the different facets of his identity, just as Humbert tries to describe the different facets of Lolita.

And Frida brings another rare skill to the table. She has a knack for channeling sexuality in unexpected ways. (Unibrow, anyone?) This skill would surely be necessary to capture what Humbert sees in Lolita, a twelve-year-old girl–and indeed, what Lolita seems to see in herself.

Finally, and perhaps most importantly, Frida Kahlo is a feminist. She is famous for producing images of female suffering that few others could stomach: cesarean sections, murders, miscarriages and more. When she picked up a brush to paint Lolita, we wouldn’t just get Humbert’s view. We would get a raw image of Lolita’s suffering–and her survival.

Why Frida and Lolita? Frida is good at:

  • showing many facets of a personality
  • channeling sexuality in weird ways
  • portraying women’s pain

Anna Karenina should be painted by Andy Warhol.

Tolstoy tells us of Anna Karenina: Her loveliness consisted precisely in always standing out from what she wore. Who better than Andy Warhol, prince of pop art, to make her stand out in a portrait?

Andy Warhol | Coca-Cola Art Gallery

Anna and Andy can be paired on a deeper level too. In essence, Anna Karenina’s story is unremarkable. A woman has an affair. It’s as common as a can of Campbells soup. Yet, Andy Warhol, like Leo Tolstoy, has the sensitivity to turn her common story into something arresting.

Why Anna and Andy? Andy is good at:

  • high contrast images
  • fascinating you with the commonplace

Jane Eyre should be painted by Vincent van Gogh.

Misery loves company. So the saying goes. Yet, there is more to draw Jane Eyre and Vincent van Gogh together than misery.

Jane is an icon of the Gothic romance genre: a young lady in a dramatic landscape who has a brush with the supernatural–and with madness.

Van Gogh | Byron's muse

Above: It’s easy to imagine a Gothic heroine like Jane Eyre wandering down one of van Gogh’s rabbit trails.

She’s the stuff of van Gogh’s darkest paintings and the darkest moments of his life. But she could also be the subject of one of his more tender paintings.

What makes Jane different from the other heroines of Gothic romance? She is poor, plain, and most importantly, level-headed. She’s not going to faint every time her candle blows out.  In these ways, she matches up with the peasants harvesting wheat or eating potatoes who van Gogh painted with great tenderness.

When Jane Eyre asks, Do you think that because I am poor, obscure, plain, and little that I am soulless and heartless? it’s easy to imagine van Gogh’s resounding NO!

Why Jane and Van Gogh? van Gogh is drawn to:

  • dramatic landscapes
  • moments of madness
  • poor, hardworking people

Odysseus should be painted by Leonardo da Vinci.

Homer describes Odysseus as “a man of many turnings.” Who better, then, to paint him than the creator of the Mona Lisa’s inscrutable smile?

Image result for the last supper da vinci

Above: da Vinci was regularly commissioned to paint heroic figures. He would have had no trouble fitting Odysseus to his mold.

Coming from the Italian Renaissance, da Vinci would have been intimately familiar with Odysseus’s life. Most Renaissance scholars conducted deep studies of Latin and Greek texts, and da Vinci was no exception. Likewise, he was closer in time and place to Odysseus than most other painters. Like Odysseus, he sailed the Mediterranean, played the lyre, and sopped his bread in olive oil. And like Odysseus, he was devilishly smart.

Why Odysseus and da Vinci? They share:

  • an ability to mystify people
  • a connection to Greek mytholgy
  • a penchant for looking heroic (even when they’re actually kinda shifty)

What do you think of these pairings? Who would you like to add to the list?

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