Released back in September of 2017 on the Xbox One, and prepping to launch on the Nintendo Switch in April, Cuphead was a smash indie hit, both critically and commercially. Having been announced initially in 2014, its release paid off with delightful old-school cartoon visuals and airtight run and gun gameplay that would ultimately provide for some of the toughest boss fights in gaming history.

Speaking of which, Cuphead has no shortage of boss fights. In fact, the first level largely cements the game as a boss rush title, barring some retro side-scrolling levels. Yet, some bosses are surely harder than others, leaving players with no other recourse than to remove their hair, strand by strand.


Grim Matchstick

cuphead grim matchstick

Quite easily the toughest boss in all of Cuphead, Grim Matchstick, an adorable-looking cartoon dragon, is very prone to making the most stoic of gamers cry. Although the fight starts out easily enough, it quickly moves into the controller-breaking territory. Grim Matchstick’s first phase involves it levitating in mid-air while it fires small comets from its mouth, shoots rings from its eyes, and occasionally melees Cuphead with his tail from below. Meanwhile, the player has to jump from cloud to cloud, as the fight rotates around a tower.

Phase 2 swiftly ramps up the difficulty. At this point, Grim Matchstick flies around the stage to the left of Cuphead, rolling out his tongue at the bottom of the screen, like a red carpet, while malicious flame-shaped enemies attack Cuphead. In this phase, Grim Matchstick also projects fire out of his nostrils for added measure.

In a wallop of a final phase, Grim Matchstick suddenly decides he has three heads instead of one, each of which shoots fire intermittently at Cuphead, both in-direction and neutral, while one head will morph into a flamethrower and launch a large burst of fire at Cuphead.

The strategy here is quite simple: Stay as far away as possible while shooting at the beast and, with patience, you should be able to defeat him handily.


Baroness Von Bon Bon

cuphead baroness von bon bon

Initially, the fight against Baroness Von Bon Bon in the level “Sugarland Shimmy” is pretty hilarious. In an environment where rules are thrown out the window thematically with an “anything goes” vibe, Cuphead defending himself in a Candy Land-esque stage is fairly creative and well-executed. More to the point, it might be whimsical in any other scenario, but because this is Cuphead, there is no so thing as whimsy.

In the first phase of the battle against Baroness Von Bon Bon, an anthropomorphic fortress made out of candy rests at the right of the stage, while one of five mini-bosses attacks. These include Lord Gob Packer, an enemy very similar in appearance to a jawbreaker, as well as Sargent Gumbo Gumbull, an antagonistic gumball machine. The rest include Kernel Von Pop, a mad candy corn creature, as well as Sir Waffington III, a flying waffle, and Muffsky Chernikov, a homicidal cupcake.

Selected at random, multiple mini-bosses will attack. While none are especially hard, they can be very tough to endure. This comes in addition to the final phase in which Baroness Von Bon Bon mobilizes her candy fortress, where Cuphead will be pursued by her.

While mints roll out of the mouth of the fortress toward Cuphead, Baroness Von Bon Bon will launch her own head at our titular hero and will, naturally, grow another back. As the head also pursues the player around the stage, you will have to stick to the sides to dodge the giant mints.

As with most other Cuphead bosses, it’s well-advised to stay mobile. Stand still for one second and you will be struck by Baroness Von Bon Bon or one of her candy-themed minions, which is partly why she is one of the toughest bosses in the game.


Dr. Kahl’s Robot

cuphead dr kahls robot

One of the few remarkable flight levels in Cuphead, the level “Junkyard Jive!” sports one of the toughest boss fights in the entire game. From the get-go, Dr. Kahl’s robot, who shares a resemblance to Bender from Futurama, or the Iron Giant, is fairly unforgiving. Launching projectiles from his stomach and shooting laser beams from an antenna on its head, the robot lets you know you’re in for quite the battle.

In its transition to its second phase, the robot will then launch bolts at you from its mouth, as it also attempts to strike you with a homing missile and trap you with a giant magnet. The second phase then sees the giant’s head separate from its body, causing it to hazardously fly around the screen. All the while, homing missiles will still be inclined to prevent Cuphead from being absolved of his debt to the Devil.

In the boss’s final phase, Dr. Kahl finally reveals himself. The mad doctor resembles Dr. Wily in nature, both physically and in terms of wanting to do nothing but evil, and moves around in the robot’s head, which appears similar to the Koopa Clown Car ridden by Bowser and Baby Bowser from the Super Mario series. While in the car, Dr. Kahl ruthlessly fires waves of gems at Cuphead, who also must dodge oncoming electric walls.

This fight is all about reflexes. As mentioned previously, constant mobilization is a must in Cuphead generally, but idling about in this level is a gargantuan mistake for players to make. All that can really be said here is that, hopefully, you know the deal at this point in the game. As frustrating as it may be, look for the pattern in which gems are fired and that final phase should be surmountable enough.


The Devil

cuphead the devil 1

Although technically an optional boss, The Devil provides a solid final challenge. “One Hell Of A Time” presents us with he who tasked us with claiming the souls of all the bosses we’ve defeated thus far, and it does so epically. Taking place in The Devil’s lair, which is easily the most ominous stage in the game, Cuphead first faces the cartoon and beastly rendition of The Devil, as he sits in his throne, holding a trident.

In this phase, The Devil can execute multiple attacks. One involves morphing into a ram and attempting to crush Cuphead with his hands, while the second involves The Devil’s head turning into a spider and trying to kill Cuphead that way, and the third, finally, has The Devil launch a few circular projectiles Cuphead’s way.

The second and final phase requires you to head down further into The Devil’s lair, where you now recognize he is a giant. Bombarding the player with peculiar bat-like enemies, axes, and poker chips, you must almost constantly jump from platform to platform, while taking down The Devil himself. After he has taken enough damage, he will summon two minions who will heave skulls at you as well as more bat-like creatures trying to kill your buzz.

After enough time attacking The Devil, he will start to cry as tears of pain, which inflict damage, fall from his eyes, and more poker chips fall from above onto the single platform that remains for the player. Once he’s been shot enough, it will be curtains for The Devil and Cuphead will be victorious.

All told, for a final boss in a markedly difficult game, The Devil isn’t terribly hard compared to boss fights that come before it. However, the ominous buildup to it and simply knowing this is the final boss can easily cause one to trip up. Plus, it does require a degree of accuracy. Overall, you have likely learned to dodge many types of objects/enemies thus far in the game, so you are in the knowhow there, and try to stay in the air during much of his second phase. He should go down swiftly.


Sally Stageplay

cuphead sally stageplay

There are often mixed reactions with Sally Stageplay, who we face off against in “Dramatic Fanatic” on a literal stage. Some found her laughably easily, while others found her profoundly difficult. Regardless, something that sets her apart in terms of challenge from most of the bosses on this list, is that Sally Stageplay gets four phases. That alone grants her a distinct quality in challenge.

In her first phase, Sally will hop into the air frequently and come towards you like a spear, while occasionally slinging harmful fans. She will do this in her second phase as well, which has a three-story home for a backdrop. However, in this phase, there is also a baby that will drop a milk bottle from the backdrop as well as descending wind-up toy cars.

In Sally’s third phase, she appears to be dressed as an evil goddess. Complete with an annoying crew member who can injure Cuphead with a prop, as well as other moving hazardous stage items, Sally is very idle in this phase.

Phase 4 might actually be one of the easier phases in this fight. Here, Sally Stageplay is outfitted as an angel, flying around the stage as a mobile umbrella moves back and forth on the stage to try and kill Cuphead. The apparently hostile crowd will also toss an occasional rose to hit Cuphead with, though you can easily maneuver around the weaponized roses.

Overall, Sally Stageplay is by no means an unfair boss. However, as is the case with Baroness Von Bon Bon, it is a matter of endurance. Four phases is a lot in the world of Cuphead, so keep with the strategy of timely dodging and never being stationary. You’ll be golden.


So, what do you think? Were these some of the toughest bosses to you? Or do you scoff at the mere idea of Cuphead being hard? Let us know in the comments below!

Cuphead is available right now for Xbox One. Pick it up from the Xbox Store without delay.

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