>>713565369The joke was demonstrated immediately at the start of the game- the graphics of the DK Arcade are associated with old man playing gramophone, then the hot new 3d jungle jumps in and old man gets kicked out as cool new DK with sunglasses dances and listens to much more elaborate cool music in a ghetto blaster. The whole joke was "Our new game is fresher and better, and only old people care about old games that much and they're just grouching about".
It's also never really been the "canon" outside of DKC. In the interactions the Mario series has had with these subseries, DK is always treated as being the same one from the original game, exactly because otherwise you have to acknowledge that a character that was contemporaneous to Mario suddenly is a geriatric with a nephew who is NOW contemporaneous to Mario
It was always a silly joke Rare made, because they liked breaking the 4th wall, think Banjo and Kazooie being fat because they haven't had a game in years in Nuts and Bolts. Nintendo always ignored it when needed, as they are doing now