It’s not every week that I get inspired by Illustration Friday, but this weeks topic, Wings, got me thinking. Mostly I thought about flying monkeys.

I’ve always loved the Wizard of Oz, but there is something about flying monkeys that I’m drawn to in particular. As far as minions go I really think that they’re the ultimate choice. Loyal, compact, agile and snappy dressers all in one. Now that’s a minion!

At first I was going to draw an aviator style monkey. In fact I considered for a moment submitting the logo I designed for a domain I still haven’t decided what to do with, Flying Monkey Ink. I imagine it will be an illustration site at some point, ergo, the INK… or a monkey tattoo parlor. But as much as I like the marriage of flight and monkey, there was something inside me that wanted to draw a straight up Wizard of Oz flying monkey.

I spent about a half hour looking at pictures of monkeys in their natural habitat trying to figure out what my version of a flying monkey would look like and what he’d be doing, but I couldn’t come up with anything. Then the idea of a sock monkey struck me. I actually find making sock monkeys therapeutic, so I may end up making this for realz… if I can find the right colored socks. But for now he’s just a illustration of a toy I badly want.

In the beginning it was just going to be a monkey picture, but for some reason I couldn’t get the idea of Toto out of my head. Probably because my reference picture was of a flying monkey with Toto in a basket. I knew Toto was dying for revenge, and what better chew toy. At first I had them in the Haunted Forrest, but it made no logical sense. Why would a real Toto encounter a toy flying monkey? In the end I decided on a Wizard of Oz themed play room. Just look at Toto back there. He knows he’s not supposed to be here, but he just can’t help himself.