I believe it was on about the same time as Three Friends and Jerry. It was intentionally (I hope) poorly drawn. I think the main character was black with glasses and maybe a red hat. The kid had a female friend. I am pretty sure it took place in middle school. Probably Canadian, but maybe not.

I didn't even like the show that much, but I have not been able to figure it out for the last five years or so. I tried a search and none of them were the answer. I checked both wiki and the 90's section for a title that looked familiar to me. My guess is that it isn't in your data base, but perhaps someone recalls it. Please it has been killing me for years.

Stickin' Around, perhaps?
http://www.imdb.com/title/tt0275153/

The only thing that comes to mind is Disneys' Fillmore on ABCs' One Saturday Morning.

That is it. Thank you, I can finally rest easy.