Ever since December 2025, I’ve had the thought of drawing Chester Cheetah inflated, but since I’ve mainly been busy drawing things for the holidays, as well as some fanart of 1998 Rudolph since it’s one of my new favorite things, I never had time on my hands to draw out my inflated character idea. But now since it’s 2026 and I saw a few art pieces of Chester Cheetah inflated, it got me motivated to finally draw out what I had in mind! And well, like most of my recent inflation art, it turned out really good! I’ll admit that drawing Chester’s spots was a bit hard and may not be the most accurately placed or whatever, but I’d say it’s still great enough with the art I’m able to do. Oh, and of course the inflated body shape is mainly the same with most of the inflation art I’ve been making.

As for the background, it’s inspired by the Bird Houses level from the Sega Genesis/SNES video game, Chester Cheetah: Too Cool to Fool, which was honestly a pretty alright licensed video game, at least the Sega Genesis version was in my opinion. Speaking of which, the title is also a play on that name as well. Perhaps I might consider making a pixel remake of this in the future? But I’ve been really busy working on other things, so that’ll probably be saved for the future. Still, I’m hoping to make more inflation of Chester when I have more time on my hands, and the same goes for 1998 Rudolph as I mentioned earlier in the description.

Chester Cheetah is owned by Cheetos/Frito-Lay.