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Ranking The Top 10 Most Fun Cuphead Bosses To Battle

Believe it not, but Cuphead is really fun. We're going to prove that today by bringing you the top 10 most fun boss fights in Cuphead. Whilst the game is naturally designed to induce desperation and despair, the design and creativity in Cuphead mean that the game is actually packed full of many memorable encounters and hilarious situations.

Ranking The Top 10 Most Fun Cuphead Bosses To Battle Cover

Wait a second Andrew, did I just read that correctly? Fun?! Yes, you did read that correctly. Despite the fact that 99% of the time you’ll have your arse decimated and handed to you over and over again like a cartoonish nightmare of Groundhog Day, some of these bosses are a treat to face. From the off-putting backgrounds to the dynamic bosses themselves, the sheer creation and imagination of them are quite simply fabulous. So to celebrate the recent announcement of Cuphead being available on PS4, I thought we could cast a different spin on the usual notion of assigning numbers to the “hardest bosses”. Instead, we shall be ranking the top 10 Cuphead bosses in terms of how fun they are, how spectacular they are, how cool they look, and the variety of the fight. Ladies and gentlemen, this list will get red hot! Here goes!

*These opinions are based on the ‘Regular’ versions of these fights.

Also, check out the Complete 100% Cuphead Trophy List!

10. Cala Maria

Cuphead: Cala Maria Boss Fight #16

It’s very rare for a cartoon character to have some form of sex appeal, but that’s clearly what the developers were going for here…I think. Akin to the likes of Jessica Rabbit, Cala Maria provocatively wiggles her hips to distract you from the multiple waves of fish, blowfish, stone gazes, and ghost pirates she sends your way. From her snazzy octopus hair and adorable shrieks to you enduring her onslaught of fish, she certainly has plenty of character.

The constant stream of waves are nice to look at, her hilarious transformation into a Medusa-type form is spectacular, and the final phase foray into a reefy cavern will certainly grab your attention as this subtly difficult fight nears its end.

9. King Dice

Cuphead: ALL Casino Bosses / King Dice Boss Fight

Now, whilst I love the character and the design of King Dice, I don’t particularly enjoy the concept of him too much. I enjoy the ever-changing series of fights that will change if you can’t time the dice throw properly, but it’s the grind of having to start over that leaves a sour taste. I’m no stranger to this idea as I’ve completed all ‘SoulsBorneNioh’ games blah blah etc, but it does annoy me. Nevertheless, King Dice is a strong character, and this series of mini-fights has some beauties. I found some to be a lot more difficult than others, and this sort of forces my hand when I attempt his marathon.

The cowboy in the form of a stack of chips is a great example of Cuphead boss design. It’s the same three or four attacks, but because they’re so meticulously designed and paced so well, it’s still easy to mess up and lose a precious heart that you’ll need for the final stage. He’s definitely not the king of the bosses, but there’s plenty to love about him.

8. Hilda Berg

Cuphead: Hilda Berg Boss Fight #4

The words “HA” are so ironic in this fight. I’ve been laughed to death more times than Michael Jordan has sunk 3-pointers. But thankfully Hilda Berg’s fight is enjoyable enough to overlook her cruel mockery. Cloud bulls and Cloud Cupids are some of the devilish, white foes she throws at you. 

But let’s get real, the standout stage of this flighty ferociousness is THAT transformation. After another funny transition that temporarily makes me lose my concentration – every single time – Hilda says enough is enough and becomes an utterly terrifying, robot moon. If you’ve nailed the boss up until now, then this is why, because you’ll need your lives for this. Studio MDHR always finds a way to simultaneously retain Cuphead’s endless charm, yet make you want to individually pluck out each one of your eyelashes in frustration.

7. Grim Matchstick

Cuphead: Grim Matchstick Boss Fight #10

Could there BE any more things to keep on top of in this boss? Due to the ever-changing clump of clouds that act as your escalator for the level, you’re constantly having to ascend and descend, whilst avoiding everything! Phase one alone has Grim Matchstick’s tail popping up whenever it feels like it, a torrent of vibrant fireballs, and laser rings. A whole fight of this would’ve been bad enough. 

Then phase two, which is obscenely difficult enough without the homing shots, requires alternate cloud jumping going backwards and forwards whilst avoiding our derpy dragon’s best suicidal flame guards. And phase 3 is one that I still struggle with after multiple completions of the campaign. But the visuals and colors are incredible. Three windmilling dragon heads pelting you with fire and projectiles – whilst it rains and thunders. It’s not hard to see why this game took so long to make. The intricate details are exquisite, in particular, the tower in the distance that signifies you’re going in circles.

6. Beppi The Clown

Cuphead: Beppi the Clown Boss Fight #8

Truth-be-told, Beppi is one of the easiest bosses on this list. But the dynamics of the level are so enamoring that it would be a great disservice to leave out everyone’s favorite crazy clown. The carnival aesthetic is brilliant with a continuously active ferris wheel and accompanying rides. Additionally, each stage caters to a specific element of popular carnival rides. Whilst Beppi’s dodgem isn’t hard to negotiate, the shooting gallery ducks add to it.

The fight is garnished beautifully with an evil rollercoaster of carriages that sporadically appears to give you even more to take into consideration. I always appreciate that you can anticipate it though as it’s identifiable in the background of the screen, before appearing in the foreground a few seconds later to end you. Over and over.

5. The Devil

Cuphead: The Devil Final Boss Fight and Ending

Only number 4 you ask? Why did we even put this in the top 10 you ask? This is what I’ve found to be the general consensus for our cup killing, hell dweller. Some people have grown full beards before they’ve beaten him, whereas some don’t even classify him as anything special, I personally think he’s somewhere in the middle. There are definitely harder bosses than The Devil, but his fight has a lot right with it.

He has so many attacks to deal with, and his pesky purple-headed dragon dude is an absolute pain in the butt. However, The Devil’s demeanor is a joy to behold as he visibly likes to survey the chaos. Choosing a certain path and descending deeper into the fight enables you to bear witness to hell’s, horrible overlord in all of his naked glory. His face occupying 80% of the screen is unsettling enough, but it’s worth it when you see our darling devil become more unhinged and emotional as the fight goes on. It’s a perfect encapsulation of your journey thus far and is very cathartic – if you get to see it that is. 

4. Dr. Kahl’s Robot

Cuphead: Dr Kahl's Robot Boss Fight #12

The #3 and #4 entry on my list were close, but ultimately, Dr. Kahl goes forth, and his attacks certainly do multiply. The dirgy, landfill populating the background just reminds us that this robot was probably made out of most of this, so what are YOU doing with your life? One of the beautiful aspects of Dr. Kahl’s robot is the initial arsenal of destruction you get thrown at you. It’s entirely up top you how you approach him as he has three separate areas you can attack, with each destroyed area consequently giving you ANOTHER problem to deal with. So it gives you an opportunity to find out which way suits you best.

The robot’s flying head serves as an intermission before the endgame, bullet-hell you’ll be subjected to. It’s not the first boss to utilize bullet-hell tactics, but Dr. Kahl’s health bar is a bit longer than normal, requiring supreme patience and concentration. 

Side note: 3 flying bosses made this list. This is a testament to Cuphead’s ability to offer you gameplay in the form of a big selection of chocolates, as opposed to one single Malteser covered in couch fluff.

3. Baroness Von Bon Bon

Cuphead: Baroness von Bon Bon Boss Fight #6

When I think of zany, weird and wonderful fights that effervesce with quality, I think of the Baroness. The premise is so silly, but the level looks so tasty. A demonstrative cake castle is one thing, but being attacked by a comedic gumball machine with legs moving faster than roadrunner is the stuff of 4am, Redbull benders. Like, how do they manage to make candy corn look menacing? Or a one-inch jellybean – with a knife – become the most deadly aspect of the fight? It’s stupendous. Then you’ve got the cartoonish “I’ll get you” fist jabs from an increasingly aggravated Baroness.

If you continue to plague her existence with evasiveness and defiance, her rage eventually boils over and her sugar levels overload to such an extent that she mounts her cake doggy and embarks on a quest to make Cuphead a Cupdead.

2. Werner Werman

Cuphead: Werner Werman Boss Fight #15

With closer inspection, you realize that each level, and boss, has a story – further punctuated with hidden lore. Some details are really obscure and require careful inspection to truly make sense of them. Werner Werman was one of the first bosses that really hammered home this idea. When you’re knee-deep in a non-stop battle of attrition with an honorable German soldier rat of distinction (weirdest sentence ever) it does become difficult to admire the scenery. 

Then, you see his medals, you see his helmet, and the pieces all click. But as I’ve said, when you’re evading a makeshift tank, flames, deadly sawblades…and a cat, then you’d be forgiven for missing out on these finer details. This fight is equal parts tough, the cat somehow gave me a jumpscare, and the level is one of the best in the entire game.

1. Cagney Carnation

Cuphead: Cagney Carnation Boss Fight #5

Arguably the most iconic fight in the game? In my opinion, yes. I have replayed this fight numerous times for Cagney’s dance alone. Whoever decided that a giant, killer sunflower should do that dance should be given instant royalties. Furthermore, that final stage form? Jesus…I never wanted to set foot in a garden again after seeing that big grin for the first time. 

When a sunflower looks as terrifying as the Devil, then you have to bow and applaud the artists of Cuphead. The actual encounter is simple enough, with a few telegraphed attacks to dodge, and even the most seasoned Cupheaders will take the odd hit here and there as the screen can become overpopulated by flower power!

There you have it! Our official ranking of the Top 10 most fun Cuphead Bosses to battle. Who’s yours?

Let us know in the comments below!
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Joshua Stolworthy

Nice article, but Cagney is a carnation, not a sunflower. It even says it in his name!

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