According to Donkey Kong Country animator and character designer Kevin Bayliss in 2019, when Rare co-founder Tim Stamper and Nintendo tasked him to redesign Donkey Kong and "bring it up to date", he originally wanted DK's design to be "compact" similar to how NES characters were previously designed, and wanted the character to show up "nice and clearly." When designing DK's new facial features, he used the same design as the Battletoads' eyes, noting that gorillas "look like they got this big brow". He later expressed frustration in 2025 that this design choice always made DK look "annoyed", in defense of a new, contentious redesign of the character first introduced in the 2023 film The Super Mario Bros. Movie and later incorporated into Nintendo's games starting with Mario Kart World.

Many players assumed that the redesign was derived from his appearance in the film, resulting in complaints that it represented a sterilization of the character's public image. Closer to the release of Donkey Kong Bananza, the game's producer Kenta Motokura and the character's creator Shigeru Miyamoto explained their reasoning for the redesign. Motokura revealed that the design was first conceived for Donkey Kong Bananza before being applied to Mario Kart World and the film, and was made to account for the former game's 3D gameplay. He stated that they first accounted for how players would spend the majority of their time viewing DK from behind before snowballing into more substantial "creative adjustments," using his design from the original arcade game as a reference point; Motokura quipped that they "returned to where it had all started" while overhauling his design. According to Miyamoto, the redesign was intended to make DK more expressive, citing Donkey Kong Jungle Beat as the starting point to the new direction they took his design.