Concept  
This was a picture I had been thinking about doing for a long time, so when the opportunity came along I jumped at the chance. The scene is this: Alice has been shrunk down to just a few inches in size, and while wandering through a garden encounters an aloof character - the caterpillar - sitting atop a mushroom. The underside of the mushroom is exactly at the height of Alice's eyes, which is why she doesn't notice the caterpillar up there at first. The tough part was setting up the scene so the viewer could see the facial expressions of both characters simultaneously. The facial expressions themselves were also crucial - the caterpillar somewhat irritated, but also bored; Alice a little surprised, but I also wanted her to look delighted with her discovery, and curious. I did a lot of thumbnails for this one.

 
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  Planning the light  
   
Along with setting up the positions of the figures for maximum impact, I had to consider how I wanted the shadows of the main objects (mostly the large mushroom) to fall. I use cast shadows behind other lit objects to create silhouettes where I want to carve out a shape to grab the viewer's attention (more on that later). I was pretty sure what I wanted to do with the light in this one: I wanted the mushroom to cast a shadow in Alice's direction, but behind her (on the ground and foliage), not right on her. I did a couple of special purpose thumbnails to establish the main elements.
  Character design - Alice  
   
    Next I took a look at costumes from the general era of the Alice story, but I opened it up a bit, going as late as 1920 or so to see if I found something I liked. I did a bunch of sketches to explore a few ideas. I liked the sailor bib and the loose low waist, as well as the matching ribbons on her hair and waist.

     
  Character Design - Caterpillar  
   
    I also did a little research into caterpillar morphology... and was surprised to learn that they have two different kinds of legs (front legs vs. back legs). That suited my needs perfectly, since I wanted my caterpillar to have arms and legs (the story specifically says the caterpillar's arms were crossed, or folded). When doing animal characters I like to stay as close to the real creature as possible, only anthropomorphizing when necessary to create the feeling of a character. To show you what I mean, here are some other animal characters I have created.      
   
To be able to just let my pencil go and explore different character ideas, I need to study a lot of examples of the real animal beforehand - thank goodness for Google image search! Although in this case I was also fortunate enough to find a rather large caterpillar in my own garden.


     
  Drawing  
   
    For this picture I drew a slightly more detailed drawing than I customarily do, although I still did not let this lock me into compositional elements that I found weren't working as well once I added value and color.

The sketch was begun with (real) pencil and paper (some of the elements were scanned from various sketches, shown above, then assembled to create a rough composition), then finished in Painter using a custom brush that pretty closely mimics my pencil work.


     

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