Ranking All 40 Cuphead Bosses

We look at every single boss in Cuphead and its DLC and rank them.

Posted By | On 18th, Jul. 2022

Ranking All 40 Cuphead Bosses

Cuphead is a wonderful game, and with The Delicious Last Course, we now have a fantastic series of boss fights to talk about. Cuphead is nothing if not for its phenomenal fights, after all, and so here we are, ranking EVERY SINGLE BOSS in Cuphead and The Delicious Last Course. That’s right, we’re ranking all 40 bosses in the game. Now, it is worth keeping in mind that Cuphead is a phenomenal game, and both the base game and the expansion feature some of the most creatively-designed encounters in gaming. This means that even Cuphead’s most boring, dull fight is leagues ahead of the sorry excuses for boss fights we tend to get in most other games. With that out of the way, let’s get right to it!

1 – King Dice (All Bets Are Off)

There’s just something brilliant about the King Dice boss fight. Of course, it certainly helps that King Dice has been around as a character since the very beginning of the game, and finally beating him is definitely one of the best experiences Cuphead has to offer. Despite being the second-to-last boss fight in the base game, King Dice steals the show quite handily thanks to his unique design, general presence throughout the game, and fun fight. And yes, I am a sucker for a good boss-rush styled encounter.

2 – Grim Matchstick (Fiery Frolic)

Grim Matchstick is my pick for the second best fight in Cuphead because it’s quite easily one of the first fights where Cuphead’s difficulty has the potential to reach a player’s frustration threshold. Not only is a fall instant death, there are also a lot of projectiles to dodge while staying on the tiny cloud you’re allowed to stand on, all while trying to deal as much damage to Grim Matchstick as you possibly can. This is the fight that most people think about when Cuphead comes up.

3 – The Root Pack (Botanic Panic!)

Talk about first impressions! The Root Pack is likely the first boss most players will face, and it does a wonderful job of teaching players just what it is they can expect from the rest of the game. It tests several skills—avoiding attacks, keeping up with your damage, parrying—but in a relatively safe environment. The Root Pack isn’t a particularly tough encounter, but it’s a brilliant teacher.

4 – Ribby and Croaks (Clip Joint Calamity)

Right after The Root Pack, you’ll get access to Cuphead’s first dual boss. Once again acting as a sort of soft tutorial, Ribby and Croaks teach players that they have to pay attention to more than one thing at a time. Again, not a particularly difficult encounter, but the way Cuphead teaches its players how to play the game with expertly-designed encounters is just plain old brilliant.

5 – Captain Brineybeard (Shootin N’ Lootin)

Who doesn’t love pirates? Captain Brineybeard has a great design, but more importantly, Brineybeard’s also a pretty fun fight. Considering that this fight is fairly deep into the base game, Brineybeard doesn’t hold back any punches. Keeping a handle on Brineybeard while dodging attacks, avoiding the barrel, and even dealing with various sea creatures can get hectic, but it certainly makes for a fun fight.

6 – Moonshine Mob (Bootlegger Boogie)

And here’s where we see one of the first encounters from The Delicious Last Course. Having no time for yet another tutorial, one of the few fights available at the start of Cuphead’s DLC throws you right into the thick of it. Moonshine Mob has you pay attention to three different layers, all while avoiding bombs, goons, and a random enemy that shoots lightning. The Moonshine Mob is definitely a great way to kick things off with a bang in Cuphead’s DLC.

7 – The Devil (One Hell Of A Time)

The Devil doesn’t really need much of an introduction; he is the primary antagonist of Cuphead, after all, and this fight definitely puts players to the test. The Devil is an intense fight with four phases to go through, and interestingly enough, varies things up by transforming into various beasts right from the first phase. It certainly helps that finally getting to the final phase of the fight gives The Devil a mental breakdown, which is always great to watch happen to a story’s main villain.

8 – Baroness Von Bon Bon (Sugarland Shimmy)

I’ll admit, Baroness Von Bon Bon is so high in these rankings purely because of her design. In a game filled to the brim with wonderfully-designed characters and enemies, Baroness Von Bon Bon’s entire encounter is truly a sight to behold. And if fighting the Baroness by herself wasn’t enough, players will also have to deal with her castle fortress, which has a mind of its own, of course.

9 – Angel and Demon (One Hell Of A Dream)

Acting as a capstone to finish off Cuphead: The Delicious Last Course—and by extension the entire game—is the Angel and Demon fight. It is worth noting that Angel and Demon is a secret encounter that can only be accessed once you figure out a major puzzle in The Delicious Last Course. I won’t go into details here to avoid spoilers, but I’ll still talk about the fight, and what a glorious fight it is. Having to deal with both bosses at the same time is intense, since when you’re dealing with one of them, the other’s going to be affecting the fight in its own ways, be it by creating a wall of fire, or a wall of water.

10 – Cagney Carnation (Floral Fury)

And once again, we’re at a tutorial fight. Cagney Carnation teaches players an incredibly important skill: how to effectively read the enemy. Like I mentioned higher up in the rankings, Cuphead’s approach to tutorials is one of the best things about the game, since it teaches players by just throwing them into fights where they have to learn the skill, or die trying, and Cagney Carnation teaches players how to keep an eye on an enemy’s tells so that they can watch out for specific attacks.

11 – Gloopy Le Grande (Ruse Of An Ooze)

Maybe I just have a strange preference for earlier fights in Cuphead for some strange reason, but Gloopy Le Grande is right up there with Ribby and Croaks and The Root Pack as an effective way to teach players the necessary skills to survive in Cuphead. Gloopy teaches players how to constantly be on the move, how to figure out positioning, and most importantly, how to have patience. Of the tutorial fights, Cagney Carnation and Gloopy Le Grande are quite possibly the hardest ones on the first island.

12 – Chef Saltbaker (A Dish To Die For)

Chef Saltbaker’s sudden but inevitable betrayal would likely sting a lot more if it wasn’t such a fun fight. Acting as the ending of Cuphead: The Delicious Last Course’s story, Saltbaker throws just about everything he has at you. Using and abusing various ingredients as part of his different attacks, Chef Saltbaker is definitely a worthy villain to a fun story, but more importantly, his post-fight redemption makes beating the crap out of him all the sweeter.

13 – Glumstone The Giant (Gnome Way Out)

cuphead the delicious last course

Another potentially wonderful first impression, the Glumstone The Giant fight is one of two available at the start of The Delicious Last Course. Unlike the Moonshine Mob, however, Glumstone keeps it relatively simple. I am also a fan of the fact that, after spending the first phase fighting off gnomes from his beard, Glumstone gets frustrated enough that he looses all of his facial hair. If that’s not great design, I don’t know what is.

14 – Hilda Berg (Threatenin’ Zeppelin)

Here we have the first flying encounter of Cuphead—essentially a tutorial for the concept—and as you might have noticed, there aren’t any other flying encounters higher up in the rankings. While great in design, flying encounters tend to be less interesting to me because they disregard your equipment, shoehorning you into a standard moveset for the entire fight. Hilda, however, gets a pass because, ultimately, it’s still a fun boss fight that teaches you all the ins and outs of how to handle flying encounters. Hilda’s use of zodiac motifs is also quite interesting, providing her a lot of possibilities for different attacks.

15 – Phantom Express (Railroad Wrath)

phantom express cuphead

Who doesn’t like a good train encounter? The sheer weirdness of the Phantom Express encounter is truly a sight to behold. Players will have to dodge eyeballs, deal with the Conductor, and even fight off ghosts. Phantom Express definitely earns its place in these rankings.

16 – Cala Maria (High Seas Hi-Jinx!)

Not only does Cala Maria’s name make for a wonderful pun, but Cala herself is a pretty fun boss fight. Despite being a flying encounter, Cala Maria manages to be an interesting fight owing to her wide variety of attacks, which among other things include the use of sea creatures, and a head full of eels.

17 – Sally Stageplay (Dramatic Fanatic)

The Sally Stageplay encounter is involves having to deal with quite a few attacks, even in her first phase. As the fight goes on, Sally likes to use more and more of her acting chops, including background actors that will deal damage.

18 – The Queen (The King’s Leap)

Acting as the final test in The King’s Leap in Cuphead: The Delicious Last Course, The Queen will push your parrying abilities as far as they can go. Dealing with a boss by using nothing but the parry ability is an interesting idea, and while the entirety of The King’s Leap series of encounters tests your parrying skills, The Queen is the ultimate challenge.

19 – Dr. Kahl’s Robot (Junkyard Jive!)

Another encounter where the design alone puts it above and beyond most of the other bosses of Cuphead, Dr. Kahl’s Robot is a fun fight where players will have to deal with quite a few attacks, and ultimately dismantle the giant robot.

20 – Djimmi the Great (Pyramid Peril)

One of the first potential bosses on Cuphead’s second island, Djimmi The Great uses weapons like scimitars, weaponizing jewelry, and even using cats in his attacks. The Djimmi encounter is a generally grueling fight, with five phases, and a secret sixth phase that will put your flying to the test.

21 – Chips Bettigan (Inkwell Hell)

Quite easily the most memorable of all the encounters leading up to King Dice in Inkwell Hell, Chips Bettigan makes clever use of his design by having players dodge poker chips, all the while trying to keep up the damage. Like the other Inkwell Hell mini-bosses, Chips Bettigan isn’t a particularly long—or difficult—encounter, he’s memorable thanks to his design and the general motifs.

22 – Tipsy Troop (Inkwell Hell)

The Tipsy Troop is yet another example of just how wonderful the design for some of the enemies in Cuphead can get. You’re invading a den in hell. Again, Inkwell Hell bosses aren’t particularly long or memorable, but with designs like this, they don’t have to be.

23 – Mr. Wheezy (Inkwell Hell)

Keeping up with Inkwell Hell’s general motif of vices, Mr. Wheezy is a sentient cigar that loves teleporting all over the ashtray. While the fight itself is quite fun, what makes Mr. Wheezy so memorable is his death; on defeat, Mr. Wheezy is crushed by King Dice’s shoe.

24 – Pip and Dot (Inkwell Hell)

The sentient domino Pip and Dot is a duo that has a couple of interesting things going on in its fight. Alongside having to deal with Domino Birds throughout the fight, players will also have to keep avoiding various hazards in the level, and even avoid 20-sided dice. The whole encounter is topped off with platforming challenges throughout the fight.

25 – Hopus Pocus (Inkwell Hell)

The crazy magician Hopus Focus is yet another encounter King Dice throws in your way. Throughout the fight, players have to avoid rabbit skulls, and playing card-based attacks. Hopus Pocus also puts your parrying skills to the test, especially with the card attacks.

26 – Phear Lap (Inkwell Hell)

In a series of fights basically meant to slow your progress down before the finale, Phear Lap is here to test your aerial battle skills. Phear Lap is an especially intense flying encounter owing to his omni-directional horseshoe attacks, and a ghost that likes to attack you for no reason whatsoever.

27 – Pirouletta (Inkwell Hell)

After fighting a sentient domino, a sentient roulette wheel is the obvious next choice. Pirouletta’s fight isn’t particularly memorable, all things considered, but her fight’s still quite fun. Dodging boomeranging poker chips and Piroletta’s dance moves can be quite the challenge.

28 – Mangosteen (Inkwell Hell)

Mangosteen ends up feeling like one of the weaker encounters in the line-up of Inkwell Hell mini-bosses. Mangosteen only has one real attack that ends up being quite easy to dodge. The real challenge in the fight comes from having to deal with billiard chalks dropping from the sky.

29 – Mr. Chimes (Inkwell Hell)

Mr. Chimes ends up being last in our rankings amongst the Inkwell Hell encounters because it’s a flying encounter, and not a particularly memorable one at that. The only worthwhile mechanic in this fight is having to deal with cards; picking the wrong cards makes Mr. Chimes faster, but not picking any cards for a few seconds slows Mr. Chimes back down. Thankfully, Mr. Chimes has a great design, and there’s something about a mechanical monkey with cymbals that always manages to bring a smile to my face.

30 – The Pawns (The King’s Leap)

The first encounter in The King’s Leap quite handily sets the tone for the rest of the series of encounters. Revolving around getting you to practice your parrying skills, The Pawns is an encounter where you have no other tools but jumping and parrying. Having to deal with an army of small pawns running all over the place is quite hectic, especially when you have to perfectly time your parries to win the fight.

31 – The Knight (The King’s Leap)

cuphead the delicious last course

The second King’s Leap fight revolves around dealing with an enemy that can actually attack. The Knight is a fun fight because it has a number of attacks to deal with, all with you only being able to use your parrying skills.

32 – The Bishop (The King’s Leap)

The chess motifs continue with The Bishop—the third Kings Leap encounter. The Bishop likes to make use of diagonal movement and sending his extra heads out to attack you. Once again, armed with nothing but your parrying skills, players have to deal with The Bishop’s variety of attacks to progress further in The King’s Leap.

33 – The Rook (The King’s Leap)

Quite easily the most personality-filled encounter in The King’s Leap, The Rook’s introduction alone was enough to make me like the fight; he’s spending his time dreaming of a female guillotine to spend his life with, after all. The fight itself is also the most intense test of your parrying abilities aside from The Queen. Ultimately, however, it is still just a test of your parrying skills. If you’ve been practicing, The Rook goes down just like any other boss.

34 – The Howling Aces (Doggone Dogfight)

Make no mistake—The Howling Ace is a fun fight. Sadly, however, it isn’t particularly memorable. The fight is mostly held up by its excellent art design, and when it comes to actual difficulty, The Howling Ace isn’t all that bad. Sure, there are quite a few things to deal with throughout the fight’s 3 phases, but they’re all surprisingly manageable. The Howling Aces is an excellent reminder that even when the fight’s fun, in a game like Cuphead, it is easily overshadowed.

35 – Rumor Honeybottoms (Honeycomb Herald)

As an encounter, Rumor Honeybottoms features some clever ideas. The general insanity of the fight, coupled with the fact that it’s a vertically auto-scrolling level leads to a fair bit of stress in the fight. But overall, the fight ends up feeling like you’re spending more time fighting smaller enemies rather than the boss itself. Phase 2 and 3 get better about this, having you fight  the boss head-on, but considering the nature of the game means that you’ll be fighting through the first phase more times than any of the other phases, fighting worker bees just isn’t all that fun.

36 – Beppi the Clown (Carnival Kerfuffle)

cuphead bosses

In a game filled with unique and memorable boss designs, Beppi the Clown sure feels like a bit of a disappointment. Don’t get me wrong, though, the fight is still quite fun. Having to dodge a bumper car, dealing with cardboard ducks, and then seeing the boss turn into a helium balloon is exactly the kind of insanity I love Cuphead for. But Beppi’s overall design really brings down this fight in the rankings for me.

37 – Mortimer Freeze (Snow Cult Scuffle)

Cuphead The Delicious Last Course

Mortimer Freeze’s biggest problem is that, after having dealt with fights like Glumstone and the Moonshine Mob, Freeze ends up feeling surprisingly manageable. Don’t get me wrong, there are plenty of insane attacks to avoid, all while having to keep up your damage. But ultimately, from a boss that’s supposed to be a cult leader, Mortimer Freeze just doesn’t do enough to set himself apart from some of the other, more interesting fights in the game.

38 – Wally Warbles (Aviary Action)

Have you noticed I don’t like flying encounters yet? It’s a real shame that Wally Warbles is a flying encounter, because I generally love the idea of a bird stuck in a bird house that’s also a cuckoo clock for some reason. Wally Warbles is also quite a difficult fight, with attack patterns rivaling some of the easier bullet hell games out there, but it doesn’t matter how much you dress it up, I just don’t think the flying encounters are particularly fun in this game.

39 – Werner Werman (Murine Corps)

Werner Werman’s army motifs feel like a bit of a downgrade when it comes to the design and general art direction for the encounters in Cuphead. Oh, they definitely manage quite a few jokes along with a generally decent fight, but after having dealt with a dragon, a pirate, and even a sea siren, dodging attacks from literal cannons just doesn’t scratch the same itch.

40 – Esther Winchester (High Noon Hoopla)

cuphead the delicious last course

Unfortunately, we weren’t done with the flying encounters in The Delicious Last Course. As a boss, Esther Winchester is a great visual gag on the idea of a cowgirl, and thematically, the fight is still pretty great. But I only wish it wasn’t a flying encounter. With the sheer number of cool equipment, and even the unique moveset offered by Miss Chalice thrown out the window in this fight, Esther Winchester is a pretty big let down in an otherwise phenomenal DLC.

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