Hardest Cuphead Boss To Easiest, Ranked

by Sameed Khan · Published November 2, 2017 · Updated September 20, 2020

Cuphead takes inspiration from vintage entertainment for both its art design and gameplay. The indie title looks like a 1930s cartoon and plays like an NES-era game. The unforgiving nature of the boss rush game may have caused the rage-fueled demise of countless gamepads, but that’s what makes beating it so satisfying. Its difficulty also makes it an ideal candidate for a boss ranking list.

We put together a boss difficulty ranking for Dark Souls III, and in what follows, we’re going to do the same for StudioMDHR’s Cuphead as well. The ranking is, of course, based on our own maiden playthrough of the game, though we did take polls from across the web and chatter over social media into account whenever we felt torn as to the place of a boss in the list.

Let’s get right into it, starting from the easiest boss in the game and going all the way up to the hardest one.

19. The Root Pack (Botanic Panic)

The Root Pack poses little threat to the seasoned gamer. Widely considered the easiest Cuphead boss, this trio of vegetables, aptly encountered early in the game, practically serves itself on a platter, ready to be sauteed. All three phases of the fight are quite straightforward, with the only challenge being the homing carrots in the last one, which could swarm the unwary player if ignored.

18. Goopy Le Grande (Ruse of an Ooze)

You wouldn’t expect much of a challenge from a blue bouncing ball with hardly any variety to its attacks, but Goopy Le Grande does have the potential to catch players off guard, specifically during the first two phases of the fight, where he tends to bounce off the edge of the arena and right on top of your head.

17. Ribby & Croaks (Clip Joint Calamity)

For most, Inkwell Isle One’s frog duo is the first real challenge of the game. The battle with Ribby and Croaks starts, like most others in the game, with a set pattern, that once memorized, is quite easy to beat. The real fight starts when the two amphibian boxers merge into a slot machine a la Voltron, as frogs do. The boss can only be damaged when the slot machine is activated, with players having to fire off shots at it while simultaneously dodging one of three series of moving obstacles.

16. Hilda Berg (Threatenin’ Zeppelin)

Cuphead is adored for its wacky boss designs and Hilda Berg takes that sharp segue from reality to a whole new level. The first plane fight of the game sees the player facing off against wildly different transformations that take up most of the screen, and for the first time in the game, the boss randomly picks between two transformations through the third phase of the fight. The fourth and final phase is the hardest, however, with players having to dodge multiple projectiles while also dashing to avoid tractor beams from UFOs flying across the top of the screen.

15. Werner Werman (Murine Corps)

This homage to the classic Tom and Jerry cartoon show offers one of the simpler challenges in Cuphead, with much fewer transformations and variations compared to the other bosses from the same portion of the game, that being the third and penultimate world. After the likes of Rumor Honeybottoms and Dr. Kahl’s Robot, this cat and mouse duo feels like a walk in the park.

14. Sally Stageplay (Dramatic Fanatic)

This deadly stage actress can prove to be quite challenging through your first few tries, though that difficulty is brought down drastically with the Smoke Bomb Charm equipped. The most troublesome phase of this boss fight would be the second one, where, in addition to mechanical mice scampering across the floor, you have to be on your toes for hostile babies dropping milk bottles from random windows in the backdrop. Equipping the Chaser and Smoke Bomb should make said portion a breeze as well.

13. Cagney Carnation (Floral Fury)

In addition to being the most challenging boss in the Inkwell Isle One, Cagney Carnation is the first Cuphead boss that uses a platforming element for added challenge. The three platforms truly come into play in the third and final stage of the battle, which restricts players to one platform at a time while chucking projectiles at them.

12. Baroness Von Bon Bon (Sugarland Shimmy)

The creatively named candy queen of World 2 is not to be taken lightly. Positioning is key in the first three phases of this battle, as Baroness Von Bon Bon’s random selection of minions can easily box you into a corner, making it hard for you to dodge the armed jelly beans that come running out of the frosted castle’s mouth every now and then. The final phase might look quite daunting at first blush, but all you really have to worry about here is timing your movements with the Baroness’s detached head, which takes a second of rest between its own. The Chaser can prove to be an invaluable secondary weapon for all phases of this fight.

11. Beppi The Clown (Carnival Kerfuffle)

Yet another reason for people to dislike clowns, this nefarious carnival comic combines a variety of minions and platforming challenges to keep players on their toes. The first two phases are quite straightforward, but having to jump over the roller coaster while also trying to avoid a bevy of horseshoes in the third can ruin your day. The best way to avoid said situation is to stand below the boss through this phase when possible. In the fourth and final phase, it’s safer to do away with the penguins as soon as they fall to the bottom of the screen as they can force you off the swings as the roller coaster speeds across the bottom.

10. Captain Brineybeard (Shootin ‘n’ Lootin)

The first phase of this battle is at the very least as easy as most fights in both Inkwell Isle Two and Inkwell Isle Three. The ship’s energy beam attack and the awkward height of its vulnerable uvula, combined with the constant threat of the hanging barrel can make the third phase a pain, especially if you didn’t save your super for last. Through my first playthrough, I didn’t consider that you could duck under the energy beam, which made this portion of the fight even harder.

9. Wally Warbles (Aviary Action!)

This cuckoo bird would be much higher on this list if there weren’t for the relatively easy first and final phases of its fight. Sticking to the extreme left of the screen in the first phase makes dodging most attacks a walk in the park. If the barrage of hostile feathers in the same phase seems daunting, you could use dash to survive the sequence and deal damage during the small attack window before the next barrage. The second phase, however, demands a lot of focus. Not only do the revolving eggs block most of your shots at the boss, they will at times choose to expand right as the bird zips across the screen at top speed, making them a pain to dodge. Saving your super meter for this phase is recommended.

For the final phase, the best way to deal damage would be to drop bombs onto the boss from above using the alternative weapon, or if you have HP to spare, you could try squeezing into the bottom-left corner for some free hits.

8. Djimmi The Great (Pyramid Peril)

The sheer length of the battle with Djimmi the Great alone earns the red genie a high place on this list. Combine that with the three variations in the first phase and the huge spike in difficulty in the fourth, and you’ve got a fight that challenges both your skill and endurance. The first three phases are quite easy to get through unscathed with a little practice, where the third phase is best passed sticking close to the boss or right above him while using the alternative, high-damage weapon. The fourth and fifth phases should ideally be fought with full HP and super meter.

7. Cala Maria (High Seas Hi-Jinx!)

Many might place this cross between Medusa and Ariel in their top five hardest Cuphead bosses given the amount of variations in the first phase of the battle. With the right RNG, however, even the hardest parts of this phase and the ones that follow tend to become surprisingly easy. For example, I had the most trouble with the electric dolphin when combined with the barrage of blowfish, but while the combination almost always took at least one health point from me despite my best efforts, there were times when I got through the same attack unscathed, without trying.

As for the second phase, the best way to give yourself more time to break out of Cala’s stone gaze is to stick to the left edge of the screen. I noticed that taking out two to three of the eels closest to you reduces the chances of you getting hit by a projectile after the boss renders you immobile. Save up on your super meter during this phase, and the third final one becomes all that much easier.

6. Phantom Express (Railroad Wrath)

One of the most satisfying fights of the games, the bout with this ghost train makes heavy use of the parry mechanic. The boss seems quite difficult on the outset but sticking to a precise pattern of attack brings that difficulty down several notches, as there is very little variation in its own pattern. That is easier said than done, however – mistime a single parry and things can go south very quickly.

The Chaser or Spread are practically essential to deal with the eyeballs during the first phase of the fight. You must stand close to the left lever while firing off your shots, ready to parry any pink ingots that dare fall on it, or you could shoot the flying pumpkins that carry them. You can fight through the entirety of the second phase without moving the platform – for each of the skeleton’s attacks, there is a safe portion of the platform to stand on.

The third phase becomes a breeze if you immediately move the platform to one edge of the screen and hit one of the two Blaze Brothers with everything you’ve got before they can start attacking. With one down, you can take your time with other, carefully dispatching any ghosts that may try to move your platform. For the final phase, all you really need to do is keep the platform at the middle of screen.

5. Grim Matchstick (Fiery Frolic)

The green dragon of Isle Two is much harder to beat than it has any right to be, and for all the wrong reasons. Adding a platforming element to a boss fight is one thing, but completely randomizing the generation of those platforms makes its difficulty much too reliant on RNG. Simply put, any fight with Grim Matchstick could be prove to be unfairly difficult if you’re unlucky with the position or number of platforms appearing on the screen.

This becomes particularly apparent in the third phase of the fight, where the dragon grows two more heads and takes up half the screen, spewing fireballs that, when shot, divide into four more projectiles, further restricting the player’s movement. The second phase is equally difficult with the boss occupying the bottom-left corner of the screen, which make it harder to hit him with most weapons while the fireballs marching along the bottom make it more difficult to move around. Using the Lobber or Chaser for second and third phases does make dealing damage a tad easier, but there is no solution for the platforming problem apart from improvisation.

4. Rumor Honeybottoms (Honeycomb Herald)

Rumor Honeybottoms has much of the same problems as Grim Matchstick with the addition of projectiles that are much harder to dodge. The first phase is utterly forgettable when it comes to difficulty, but as soon as the queen bee herself jumps into the fight, chaos ensues. The easiest attack to dodge in this phase would be the two parryable spheres that slowly follow the player around the arena. The projectile-firing rectangles require some getting used to, but are manageable.

By far the deadliest attack in the bee’s arsenal is a barrage of zigzagging missiles, which are a pain to dodge, as you have to keep an eye out for the next missile in line every time you jump away from one. This is compounded by the arena taking away some platforms at random, reducing the number of safe places you can jump to.

The final phase sees the boss transform into a plane and fly to the bottom of the screen. The Lobber or Chaser are recommended for this phase as these will allow you to fire away at the boss down below without having to aim.

3. King Dice (All Bets Are Off)

None of King Dice’s mini-bosses are difficult on their lonesome, and neither is King Dice himself, per se. The battle with the Devil’s right hand man is more of an endurance battle than any other fight in the game as well as a test of how comfortable you are with the parry mechanic.

The reason we haven’t placed this boss fight at second place is that while parrying is essential, and its timing, critical, to land the right dice rolls, the marching cards King Dice spawns in the final phase – parrying which is what most players seem to have trouble with – can be avoided altogether. You can read all about that or watch our video guide right here: How To Beat Cuphead’s King Dice Boss The Easy Way [Guide].

2. Dr. Kahl’s Robot (Junkyard Jive)

The fight with Dr. Kahl’s Robot has two of the most projectile-heavy phases in the game. This ode to bullet hell games tries its best to trap players in the very first phase, which requires the player to destroy three separate weapons on the Iron Giant look alike’s body before destroying the heart to progress to the next phase, all while the robot begins spawning additional obstacles and stronger projectiles, including but not limited to those annoying homing missiles that can take away your HP with an AoE blast when destroyed.

If you manage to get through the first phase, you’re afforded some respite in the form of a relatively easier second phase. Once the third phase begins, however, you’re back to clenching and tapping into the powers of The One to dodge an onslaught of countless projectiles filling the screen, which is made worse by electric barriers that both restrict your movements and prevent regular attacks from reaching the boss. We’d recommend equipping the Twin Hearts Charm for this battle, at least for your first few tries.

1. The Devil (One Hell of a Time)

It shouldn’t be surprising that the main baddy of the story is considered the hardest boss of the game by many. In the first phase, in addition to the three attack variations that I still haven’t figured out how to dodge and three different transformations, purple imps will run out from behind the Devil’s throne, then scamper across the foreground to ruin your day.

All of this is nothing compared to what players have to face during the second phase – whirling axes, an exploding bat that must be parried, and flaming poker chips fall from above over one of five platforms. These platforms are reduced to three as more damage is dealt to the boss, with a different set of minions filling up the screen, and finally to one. The frequency of falling poker chips increases each time. When there’s just the one platform remaining, it takes lightning reflexes – unless lady RNG is on your side – to jump away from falling poker chips and dash back to the platform while also avoiding or parrying the Devil’s tears.

Do you agree with our list? Which boss was hardest for you? Sound off in the comments section below!

You may also like to check out this remix we made for the Inkwell Isle One soundtrack.