These Two Have Appeared In The Same Thingさんのイラストまとめ

Squidward Tentacles (SpongeBob SquarePants) and Joe (Blue’s Clues) appeared in a 2002 Nick promo together

James Bond and Jigglypuff (Pokémon) almost appeared in Super Smash Brothers Melee

The Honey Nut Cheerios mascot appeared in a commercial for the cereal alongside Sonic the Hedgehog in 1994

Peter Griffin (Family Guy) and Ryu (Street Fighter) appeared in American Dad vs. Family Guy Kung-Fu II together

Aigis (Persona) and Yang Xiao Long (RWBY) appeared in BlazBlue: Cross Tag Battle together

Silver Surfer (Marvel Comics) and Hank Hill (King of the Hill) appeared in a Fox Kids promo together

Piglet (Winnie the Pooh) and Sephiroth (Final Fantasy) appeared in Kingdom Hearts together

Joker (Persona 5) and Jinjo (Banjo-Kazooie) appeared in Super Smash Brothers Ultimate together