I asked Grok “Can you tell me the first instance of fan art in which someone drew South Park’s Craig Tucker with his black hair visible with his blue chullo?” and it processed for some time and then returned me some known info that is obvious but then… and I shit you not… it provided me something OLDER than even I was aware of.
This drawing by artist Team Rocket from published Mar 15, 2005 could very well be one of the earliest pieces out there with Craig having black hair, 2 years before his hair was canonized as black in “Lice Capades” and a decade before “Tweek X Craig”
“Tweek vs. Craig” dropped June 23, 1999, so the whole shipping them would probably have started after that episode.
OMG Grok! You actually provided potentially useful in providing older data!
I am not going to lie… I am actually f’n impressed!
Artist: TeamRocket | https://www.deviantart.com/teamrocket