Here are some of the Cave Drawings I did for Starter Squad Episode 9 by @Shippiddge. I should have posted these a while ago, but better late than never I suppose. I'm gonna post the rest the drawings in a chain.
You can also watch the episode here:

The idea is that Shipp wanted the Caterpie to have drawn many different ways of Charmander's demise and that they looked like "Children's drawings." Most of these I came up with on the fly and might be a little repetitive as we go along because there's over 40 of them.

Here's two straight forward assassinations and two sadistic tortures lol

I think a couple of these might of been a bit too elaborate or overkill to be depicted as a simple illustration. But I guess they're mixed in with a more straight forward pokemon death

Charmander's worst nightmare

I think what makes these funnier to me as I drew these, is how absurdly impractical the Caterpie's stubby bodies are to physically achieve any of these actions

Another adorable existential nightmare for Charmander lol

At this point I was having a tough time coming up with ways a caterpie could kill Charmander, so I resorted to drawing other Pokemon doing the dirty work for them

Definitely the most brutal kill out of all the drawings. Shipp considered not using this one, but then instead made it the centerpiece of all the illustrations. I'm glad that he changed his mind :)

If I was a caterpie in the Starter Squad world, I wonder if I would have been appreciated for my ideas to destroy the enemy or would my caterpie brethren take me as a psychopath?

More outsourced pokemon assassinations

Anticipation and follow through

I wouldn't mind inking and colouring this one some day. I enjoy the perspective of it.

Looking back, making these doodles was a fun afternoon