The Cuphead meme stems from the 2017 run-and-gun indie game famous for its hand-drawn animation and brutal difficulty. Central to the meme's popularity are the 'Don't Deal with the Devil' intro sequence and the various expressive boss characters like King Dice. It is commonly used to illustrate situations where someone makes a high-stakes mistake, faces an impossible challenge, or experiences extreme frustration. The unique retro aesthetic allows creators to contrast the charming visual style with dark humor or modern gaming struggles, making it a staple in the gaming community.