I just thought of this and liked it a lot, most likely won't age well but it was still fun to make

Connections between the two:

• Both are indie video game protagonists with heavily stylized, era-specific aesthetics (1930s rubber-hose vs. modern GLITCH web-animation style).

• Both fight alongside sentient, living objects that double as extensions of themselves (Cuphead is a living vessel holding magical liquid; Kit fights with Kaboodle attached to her spine).

• Both can shift their combat styles on the fly by instantly swapping out their gear mid-combat (Cuphead switching shot types; Kit changing armor skins).

• Both act as "bounty hunters" forced to track down specific items for a higher authority (Cuphead collecting soul contracts for the Devil; Kit collecting game progression assets for the Farcade).

• Both are trapped in systems controlled by overarching factions (The Devil's casino debt vs. The Farcade).

• Both are absolute physics-breakers who ignore the standard rules of their environments (Cuphead using unpredictable Toon Force; Kit using external System Authority).

• Both are defined by their contrast of Naive Ambition vs. Bitter Experience (Cuphead is a reckless kid blindly trying to beat his game to save himself; Kit is a traumatized adult who knows firsthand that beating the game deletes the universe) 

Hope y'all enjoy!

"No Winners in Inkwell" Kit Bodega vs Cuphead (Glitch Productions vs Studio MDHR) Debate Chart