Thank you for this wonderful meta post about a wonderful thing.
I think Charles Barkley has been extremely memeable his whole career, but I especially think the Barkley Shut Up and Jam game for SEGA Genesis coming out just a few years before Space Jam must have something to do with it. I have a special place in my heart for the incredible games-as-memepost Barkley, Shut Up and Jam: Gaiden series.