Top 15 Hardest Cuphead Bosses (Ranked)

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Back when it first came out in 2017, Cuphead was hailed as “the new Dark Souls” – much like any other high-difficulty game in the last few years.

In this case, it might be true.

Not only will you need to hone your skills battle after battle to progress, but most of these hardcore boss fights require plenty of trial and error before you learn your foe’s patterns and find their openings.

If you’re still unsure about which bosses are just the absolute worst, join me as we take a look at Cuphead’s most challenging boss fights. Don’t let them take you by surprise!


15. Ribby & Croaks – World 1

Ribby & Croaks – World 1 Cuphead Boss

This pair of martial arts lovers are more about psychological warfare than actual difficulty.

They look like bullies, their faces are infuriating, and they’re intimidating because they’re among the first bosses you’ll fight.

After you’ve dealt enough damage, they’ll do the classic Ornstein & Smaug move and fuse together, becoming a giant slot machine that performs different moves depending on your luck.

The hardest part about this battle is avoiding the Battletoads flashbacks, which can become demoralizing once you’ve lost once or twice. But keep calm and persevere, and you’ll be moving on to the next stage in no time.


14. Sally Stageplay – World 3

Sally Stageplay – World 3 Cuphead Boss

Slightly more difficult than our previous contenders is Sally Stageplay.

You’ll see most of her moves coming from a mile away, allowing you to prepare and dodge easily. The fact that she remains in your line of fire for almost the entirety of the fight also helps.

The reason she’s even on the list is her second phase. There are just too many things happening on the screen at the same time to keep track of everything.


13. Hilda Berg – World 1

Hilda Berg – World 1 Boss from Cuphead

Hilda Berg is on a whole other level compared to the rest of the first area’s bosses.

And she actually made me drop the game for a few weeks after numerous failed attempts.

After calming down (and playing some Gradius as training) I came back and beat her on my first try.

It’s a pretty simple fight if you’re used to shoot-em-ups, but you need to keep your calm.

Her patterns aren’t too intricate, but some of her attacks are deceptively fast, requiring your full attention and fast reflexes.


12. Wally Warbles – World 2

Wally Warbles – World 2 from Cuphead

This father-and-son combo can be one of the most frustrating fights in the entire game. But it’s not nearly as bad as long as you breathe deeply and go with the flow.

Easier said than done, right?

What makes the fight so intense for some is that the bird duo doesn’t give you a lot of room to move around to rest and collect your thoughts.

That said, you should be fine as long as you stay on the leftmost part of the screen. This should give you enough time to dodge eggs, feathers, and other hazards carefully.


11. Baroness Von Bon Bon – World 2

Baroness Von Bon Bon – World 2 Cuphead Boss

This queen of Candyland is a bit of a divisive subject among Cuphead fans.

While some find the fight nigh-impossible, others regard it as one of the easiest. The reason?


The Baroness summons candy lackeys to do her bidding during the first phase of the fight, and they’re not always the same.

If you get lucky, she’ll summon easy enemies like Sargent Gumbo Gumbull (gumball machine) and Lord Gob Packer (jawbreaker).

But if you’re unlucky, you’ll meet the hellish Muffsky Chernikov (muffin), who’s arguably more problematic than the Baroness herself.


10. Captain Brineybeard – World 3

Captain Brineybeard – World 3 from Cuphead

Among all the things that make this fight hard, I’d say the game’s awkward control scheme is at the top of the list.

Especially if you’re using a gamepad.

This can be solved by remapping the buttons so you can more easily jump, dash, and aim while simultaneously shooting – which is a godsend considering the captain is at an annoying upward angle.

Also, watch out for the barrel and try to run under it from time to time when you catch a breather to reset its countdown. This will keep it from coming down on you when you’re busy dodging a cannonball or something of the sort.


9. Beppi the Clown – World 2

Beppi the Clown – World 2 Cuphead Boss

This Pennywise wannabe relies on confusing you with its 1001 attacks and phases, so you can’t catch the “flow” of the battle.

Balloons, crash test dummies, and horseshoes come from every direction. And don’t get me started on the damn rollercoaster.

It feels as if someone got confused and put a boss from the third isle into the second.

There’s no easy way around this – you’ll have to learn the patterns and probably get a little lucky! But you can make it a bit easier on yourself if you equip the Spread shot.


8. Djimmi the Great – World 2

Djimmi the Great – World 2 Boss from Cuphead

Even shoot-em-up enthusiasts will find Djimmi the Great challenging. And if this is your first aerial rodeo, you might feel like it’s impossible at first.

His hat will chase you, he’ll send a giant puppet version of yourself after you – simultaneously poking fun at the fact that you’re doing the Devil’s bidding – and he’s generally pretty annoying.

The background can also be very distracting, which adds to the challenge.

If years of social media addiction haven’t destroyed your attention span and you manage to ignore the background, you should be successful after a couple of attempts.


7. Phantom Express – World 3

Phantom Express – World 3 Cuphead Boss

Most people won’t necessarily find the Phantom Express all that hard. Especially for such a late-game boss.

Still, trying to deal damage while staying on the moving trolley and avoiding this spooky boss’ attacks can be tricky at first.

Through trial and error, you’ll eventually learn their patterns and make it through the first phase unscathed.

For the second and third phases, try hugging the screen edges, and you should find it much more manageable.


6. Cala Maria – World 3

Cala Maria – World 3 Cuphead Boss

I’m a simple man.

I see a hot mermaid, and I’m instantly mesmerized. That’s probably the reason why I find this fight so damn hard.

You might also get distracted by her adorable minions. I mean, look at those cute blowfish!

As if hypnotically swinging her hips wasn’t enough, Cala Maria will start turning you into stone during the second and third phases of the fight. There’s no way to avoid this, so your best bet is trying to plan a relatively safe trajectory whenever she’s about to freeze you.


5. Rumor Honeybottoms – World 3

Rumor Honeybottoms – World 3 Cuphead game

Much like Beppi the Clown, the fight against Rumor Honeybottoms relies on overwhelming your senses with information to make you miss.

There are explosive hazards, flowing honey, bee law enforcement, and even some private bee citizens flying around trying to end your climb up the honeycombs.

Make it through that, and you’ll have to deal with bee torpedoes and energy balls.

The fight gets considerably easier once the Queen Bee turns herself into a plane – that is, of course, if you brought the Chaser shots.


4. Grim Matchstick – World 2

Grim Matchstick – World 2 Cuphead Boss

Compared to this classic medieval dragon and the three bosses coming up on our ranking, the last spots might as well be filler.

This fight is a severe difficulty spike in the second isle.

Not only are some aspects of the fight randomized – meaning you can’t memorize all of the patterns – but the moving cloud platforms you have to jump on are the same color as the clouds on the background, which may confuse some people.

The fireballs that split up into smaller ones during the last phase of the fight killed me more times than I’d like to admit.

There’s no easy way to beat this scaly threat – except perhaps enlisting some Co-Op help.


3. Dr. Kahl’s Robot – World 3

Dr. Kahl’s Robot – World 3 Cuphead Boss

Frustrating to the point of feeling unfair, Dr. Kahl’s Robot is intense from beginning to end.

Not only is there no room for errors – there’s no room to move around in either!

Giant magnets and massive lasers make the fight feel like trench warfare, and don’t make me get started on the homing bombs.

To clear this level you’ll need to think one step ahead at all times.

Always keep an escape route in sight, and pray your parry skills don’t fail you.


2. King Dice – World 4

King Dice – World 4 Boss from Cuphead

The thing with fighting a kingpin is that you have to get through their lackeys first.

And King Dice has plenty of them.

While not much of a fighter himself, this sinister swindler will make you fight at least three mini-bosses before you get to him, without healing – and it can go up to nine if you’re unlucky.

Luckily, it’s pretty easy to avoid his marching cards once you’re done with that. After all, you couldn’t have gotten here without some pretty good parrying skills.

If you’re really stuck have a look at this guide for some advice.


1. The Devil – World 4

The Devil – World 4 Cuphead Boss

After the torture of Dr. Kahl’s Robot and King Dice, I thought The Devil couldn’t possibly be any worse.

Oh, how wrong I was.

As expected from the game’s final boss, The Devil is relentless in his onslaught.

Even if you’re a gaming god with the reflexes of a 15-years-old e-sports player, moves like the hoof arm are impossible to figure out without a lot of trial and error.

Add the annoying minion spawns and you have legitimate gaming hell.

Just keep trying (or maybe watch a walkthrough) and I’m sure you’ll be successful.

Finally, Inkwell Isle will be freed from this furry demon’s grasp.

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Nelson Chitty

Nelson Chitty is a Venezuelan expat living in Argentina. He’s a writer and translator passionate about history and foreign cultures. His ideal weekend is spent between leisurely playing games of Civilization VI and looking for the next seinen anime to marathon.