Mint_Raccoon

Jet Set Radio

It’s through Proton, but the game runs flawlessly. Do note that you’re really going to want a controller for this one. Playing this with a keyboard is a miserable experience. Another thing is that there’s an unofficial tool for importing images over your custom graffiti, but it’s for Windows and I’ve never tried it with Wine.

I’m happy with the 8bitdo controllers I’ve picked up. They’re great if you like the official controllers, but want something wireless.

This might not be as old as you’re looking for, but there was a really good homebrew painting program for DS called Colors. It even had pressure sensitivity on DS and DS Lite (but not DSi or 3DS consoles because their touch screens just didn’t have that feature).

Don’t forget that DarkMateria also did The Worf Song and Frame of Mind.

Since they haven’t been mentioned yet, I’d like to recommend all three Klonoa games on the GBA. There’s Empire of Dreams and Dream Champ Tournament which are both platformers with some puzzle elements. The third game is Klonoa Heroes, which is an ARPG (making it totally different from anything else in the series). Do note that Heroes wasn’t released outside Japan, but there is a translation patch available.