Character crossovers are not a concept reserved for big box office cinematic universes. Arguably, the idea was birthed by animated shows with "Scooby's All-Star Laff-A-Lympics," "Cartoon All-Stars to the Rescue," and most famously, "The Jetsons meet the Flintstones" 1987 movies. Even Marvel had their share of crossovers before becoming a Hollywood sensation — Spider-Man blended in with the X-Men in their respective '90s cartoons, and the Fantastic Four's The Thing met "The Flintstones" way back in 1979. Needless to say, there's plenty of precedent for a crossover between "The Cuphead Show!" and another animated franchise.
There are endless television programs that "The Cuphead Show!" could cross over with. The Netflix Animation subsidiary has some in-house options, including "Kid Cosmic," "Aggretsuko," and "Hilda." Arguably, the style of "The Cuphead Show!" would be best fitted with cartoons that have done crossovers before, like "Scooby-Doo" or "The Flintstones." But Cuphead would be even better served blended with a vintage style animation from the era it tries to emulate, such as "Tom and Jerry," "Betty Boop," or the Walt Disney animated characters. However, when showrunner Dave Wasson was questioned by Animation Scoop regarding which cartoon he would most like to see a crossover with, he answered by saying, "I think it would be great to see an adventure between Cuphead and Popeye."