Our picks, beyond the numbers
5 games like Cuphead we would recommend for different reasons
Cuphead's whole identity rests on two things working together: hand-drawn, rubber-hose animation straight out of 1930s cartoons, and boss fights that demand you learn an attack pattern cold before you'll ever beat it. Neither one alone would carry the game — it's the combination of gorgeous presentation and real difficulty that makes losing to the same boss for the tenth time still feel worth it. We looked for games that chase either half of that combination, or both at once.
Some of these come from the same run-and-gun lineage Cuphead itself pays homage to, others swap the boss-rush structure for a different kind of unforgiving challenge, and a couple are built specifically to be shared with a second player. Here's where we'd send a Cuphead player next.

Hollow Knight
Our first choice for demanding bosses in hand-drawn art
Hollow Knight shares Cuphead's refusal to go easy on you, with bosses that demand the same careful pattern-reading, patience and recovery from failure, wrapped in hand-drawn art that trades Cuphead's bright cartoon bounce for its own quiet, melancholic style.
We'd point a Cuphead player here first because the core skill transfers directly — learning an opponent's rhythm well enough to beat it clean — even though the game around that skill is a much larger, more exploratory metroidvania than Cuphead's boss-to-boss structure.
It's an exploration-heavy metroidvania rather than a boss-rush shooter, so expect long stretches of wandering Hallownest and plenty of platforming between the fights that will actually test you. If you want nothing but boss encounters back to back, this asks for more patience along the way.

Enter the Gungeon
For bullet-dodging with permadeath raising the stakes
Enter the Gungeon channels the same bullet-dodging instinct Cuphead's boss fights run on into a top-down roguelike, where learning a room's attack patterns matters just as much as memorizing one of Cuphead's bosses, except now a bad run ends the whole attempt.
We like it for a Cuphead player who enjoyed the dodge-and-learn rhythm of the boss fights and wants that same pressure applied to procedurally generated rooms, with a huge item pool giving every run its own shape rather than one fixed, memorized sequence.
Procedurally generated dungeons and permadeath replace Cuphead's fixed, hand-crafted boss gauntlet, so no two runs play out quite the same, and there's no guarantee you'll see the same room twice. Expect a looser, more chaotic kind of difficulty than Cuphead's rehearsed boss patterns.

Blazing Chrome
For the run-and-gun lineage Cuphead borrows from
Blazing Chrome comes from the same run-and-gun lineage Cuphead pays homage to, trading the 1930s cartoon aesthetic for a Contra-style robot uprising, but keeping the same insistence on memorizing enemy patterns and shooting your way through relentless waves without flinching.
We'd recommend it to a Cuphead player who wants to trace the genre back to its roots and see where that run-and-gun DNA actually came from, with built-in local co-op for two making it an easy game to share the way Cuphead's couch co-op was meant to be played.
There's no boss-rush structure or parry mechanic here — levels run start to finish against regular enemy waves throughout rather than building toward discrete boss encounters, so the shape of the challenge is noticeably different even with a similar skillset involved.

Broforce
For co-op chaos on an even bigger scale
Broforce takes Cuphead's willingness to be ridiculous and multiplies it, parodying decades of action-movie heroes across destructible, explosive levels built specifically for running, gunning and blowing things up with friends.
We'd suggest it to a Cuphead player who loved sharing the couch with a second player but wants the chaos turned up considerably louder, with both local and online co-op supported — something Cuphead's own co-op mode never offered online.
Levels are played start to finish rather than structured as discrete boss fights, so the rhythm of memorize-and-beat a single encounter isn't really here. Go in for destructive, over-the-top co-op mayhem rather than Cuphead's precise boss-pattern memorization.

Rayman Origins
For the art, and a gentler co-op challenge
Rayman Origins deserves a place here for the art alone — every frame is hand-drawn and animated with the same obsessive care Cuphead's cartoon world got, and its local co-op for up to four players makes the whole thing easy to share with a group rather than just one other person.
We'd point a Cuphead player toward it specifically for that visual craftsmanship, with combat used mostly to clear a path forward rather than building toward elaborate, memorize-or-die boss encounters.
It's a platformer first, with a gentler overall rhythm than Cuphead's bullet-dodging bosses, so anyone coming specifically for punishing difficulty will find this considerably more forgiving. Choose it when the art and the shared couch matter more than the challenge.