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so basically multiplayer MS paint? heck, it's a good idea!

Microsoft NetMeeting had that in the 90s, I remember it quite fondly.

It excited me as a kid haha. Between that and Comic Chat, and V-Chat I was convinced the future was now.

I kind of wish Comic Chat still existed (though everyone should be blaming it for Comic Sans)

Wasn't Comic Sans created for Microsoft Bob?

It was but it never made it into Bob because they did not manage to get it ready in time.

I'm having a hard time picturing exactly what could be so hard about getting Comic Sans "ready" in time.

Also: https://www.formgraph.com - a bit richer (multiple layers, drawing tools, social features, etc)