I think Cranky becoming a racer in the next Mario Kart and him constantly making playable appearances in the future mainline DKC games will eventually ensure him a slot in the Smash roster at some point. K. Rool's in Smash and Dixie and Funky are in Mario Kart Tour so that's plus since that's makes Cranky very likely for Mario Kart 9 along with the other Kongs, K. Rool, and the Kremlings.
I think the rumors Hyle Russell has mentioned are true that Nintendo is planning to make DKC big again like it was in the 90s and make it a top official Nintendo franchise like Mario, Zelda, and Pokemon instead of a secondary one that barely get's games anymore. I think the future is looking very bright for the DKC franchise.