November 5, Still Halloween:
The Ten SPOOKIEST Cuphead Bosses!

The kinds of people who read this website cross over pretty thoroughly with the kinds of people who probably already know all about Cuphead, one of the first video games I can think of in many years that I'd describe as visually and artistically "breathtaking" or "groundbreaking" to any degree, its tidal wave of popularity well earned by the laborious love and effort poured into its watercolored backgrounds and hand-drawn animation.

It's also been one of the most requested things for me to review this Halloween season, because while not technically focused on horror motifs, it's as rife with spooks and weirdos as you might expect from any game in which Satan is the final foe.

And since that laborious animation is pretty much the focus of the game, we'll have to be reviewing my favorite seasonally appropriate bosses with full gameplay videos rather than static, lifeless screenshots. None of these are my uploads, obviously, so be sure to at least give these youtubers a "like" for providing footage!

Cagney Carnation

It was somewhat difficult to pick #10 in this list. Most of our coming bosses are all firmly within "spooky" territory, but after that, things get a little blurrier. There's an unsettling telepathic carrot, a Dragon Quest slime and a wondeful giant queen bee we could have put here, for instance, but I feel like Cagney just slightly edges them all out when it comes to monstrousness.

This is especially due to the various plant creatures Cagney can generate, my favorite of which is the spotted pod that floats overhead. The flower gets especially dreadful towards the end of the fight, when he gets really pissed off and explodes into thorny vines, and you have to love the grisliness of his death animation.

The strange, palms-out dance Cagney does throughout the fight is also lifted straight from one of my all-time favorite Fleischer shorts, Swing, You Sinners, which is also the most ghost-packed eight minutes of animation you will possibly ever watch.

Doctor Kahl

Named after Disney animator Milt Kahl, it's a little interesting how "modern" this character feels to me. Mad scientists, robots, giant robots, and mad scientists with giant robots all go way back in our popular culture, certainly as far back and farther than the cartoons inspiring Cuphead, but they've grown so exponentially as tropes of newer comics and games that the combination here still somehow feels anachronistic. Again, that might just be me, though it was certainly Japan that ran with these themes more than we ever did during the Fleischer era.

The most interesting thing about this boss is that, when you collect the soul contract, it's specifically for "Dr. Kahl's Robot." Does that mean the robot made the deal? Would it even actually have a soul? What did it want?

Or did the doctor actually pull a fast one, selling his robot's non-existent soul in place of his own? If that's the case, I don't know why he bothers to defend the soul contract, unless he's afraid of what will happen when Satan finds out he was swindled.

Baroness Von Bon Bon

Even the most wholesome candy creatures feel to me like they should be hanging out with ghosts, goblins and demons, and there's no mistaking the Baroness's minions for anything other than monsters. There are more of them than we see here, but you'll only fight three of them, chosen at random, before battling the Baroness's entire beastly, crawling candy castle.

It's difficult for me to pick a favorite between that castle and the flying waffle, though there's a lot to be said for Bon Bon herself and her habit of pulling her own head off.

Beppi the Clown

I don't usually find clowns as "creepy" as other people do, but I can really appreciate Beppi's maniacally sinister grin and equally maniacal shenanigans. I also really enjoy how he doesn't have a round nose or a white face, which may be classic, but it isn't the only way for a character to communicate clownery.

Beppi actually seems to be both a clown and an anthropomorphic balloon, quite possibly from Balloon Land, and I want you to know that at least one artist (and one of my favorites!) has already shipped Beppi with Balloon Land's Pincushion Man.

Another person envisions Beppi with The voice and personality of "The Red Guy" (Satan) from Cow and Chicken, and I just absolutely can't imagine anything else for him myself.

Beppi as an entire killer merry-go-round is also definitely up there with the game's most dramatic boss transformations.

Djimmi the Great

I feel bad saying so, but Djimmi himself isn't high on my favorite designs in the game, I guess because he's just so simplistic and straightforward compared to some of the others. He definitely has his shae of personality, however, and the battle itself is one of the most bizarre in an already inherently bizarre game. It really kicks into high gear once the golden sarcophagus shows up, conjuring ghostly mummies from a starry portal as Djimmi himself unleashes his own eyeballs from his rubbery sockets.

The sequence with the giant marionette is also cool as hell, we get some multi-eyed pyramid demons, and the sound effects throughout, especially Djimmi's terrifying laughter, are just superb.

Mr. King Dice

This guy is a fan favorite for a lot of reasons, one being that a lot of people just find this cube headed man to be extremely sexy, so I guess you could say they'd rather jump his bones than roll them? Eh?? Right???? Eh!?!?

This embodiment of gambling is "The Devil's Right Hand Man," as he not only tells you himself, but sings for you in one of the game's few lyrical tracks, and your ultimate battle against him features a randomly generated selection of sub-bosses based on everything you might find in a casino.

Every single one of these minibosses has its unique charms, but I especially love the martini glass with the eyeball-bat olives, the bickering domino couple and the freaky, chattering 8-ball a little reminiscent of Melon Bread from Gunstar Heroes. That's probably not a big coincidence, when Melon Bread is battled by very similar random generation in what Gunstar Heroes calls even calls the "Dice Palace."

Already in the employ of Satan's minion and appropriately thematic to his domain, these bosses are probably demonic entities themselves rather than more of your fellow citizens...though it could be that they took on these forms when their own contracts were collected.

The Devil

Satan is the main villain and final boss, but not really my #1 favorite or #1 choice for "spookiest" in the game. He's still got some excellent attacks and forms, however, especially when his head transforms into a spider and his body just sort of sits there with blinding light (...deadlights?) pouring from its neck-hole. It's also pretty sweet when he goes full goat-head mode, and when his skeleton jumps completely out of his skin.

I'm loving the other demons you battle in this sequence, too, with the cutest little gargoyle-bird faces as their boss does all those weird and wonderful eyeball tricks...though this whole battle feels strangely short and simple compared to many of our other bosses.

Hilda Berg

This total cutie implies a lot of interesting backstory. All we know about any of these characters, besides that they live in a cartoon world where almost anything can be an anthropomorph, is that they all have outstanding debts to the devil, and it's hard to say how much of what we see of them is "natural" or some sort of demonic power they bargained for.

Hilda initially looks human, but quickly transforms into a zany airship-person and transforms into various constellations as she attempts to murder us with the power of astrology. If Hilda wasn't simply always a blimp-creature imbued with cosmic powers, I get the strong impression that she's someone who traded her soul to be more in tune with the stars she always loved so much.

Whatever the case, Hilda's final form is by far scarier, more dramatic and more surprising than even our battle against Lucifer. Just when you think she's done for, Hilda takes on the form of a cackling, witchy woman-in-the-moon with a nightmarishly mechanized body. She's so surreal, so threatening and so huge in this form, I'd have fully bought her as the final boss of her own entire game.

Phantom Express

This is the single most obvious choice for the list, but that's why it's not in the #1 spot. That'd just be too easy!

I'm loving the "blind ghost" exactly as much as you probably think I am, though. Many assume it's a reference to the Pale Man from Pan's Labyrinth, and I guess it could be, but I must always remind people that the same monster first appeared in youkai lore. This particular eye-palmed phantasm is honestly a little more interesting than either of them, by way of possessing a single empty eye socket in its actual head.

After a specter that spookular, the rest of the Phantom Express feels a little less imaginative, but you can never go wrong with either a giant skeleton or a train itself as a monster.

I also really enjoy that the music for this boss feels like "train music." The use of a real brass band and authentic period style for this game is impressive and every track is wonderful, but not many of them employ any particular sounds to communicate the themes of their corresponding bosses. When they do, it really stands out!

On a final note, there's actually a lot of fan-drawn porn of that blind ghost. There's also a lot of artwork, both work-safe and not, of the blind ghost and Cagney in a relationship. GOOD.

Cala Maria

So maybe you're disappointed that my #1 pick is possibly the game's single most predictable fan favorite, but we are judging, like we do even outside Halloween season, purely on monster factor, and I really feel like this one is even more of a monster - and an overall more creative fight - than Lucifer himself. I've also just never been somebody to shy away from something based only on mainstream popularity, bearing in mind I gave at least nine totally unrelated reasons I didn't like Lucario.

Even Maria's more vanilla initial form brings out some of the "sea monster" aspect too often pushed aside in cartoon mermaids. Not only is she gigantic, not only does she have a dead octopus for hair, but her main attack is to belch up the ghosts of sailors she's presumably lured to their death and eaten.

...And then the electric eels show up, and zap her, somehow, into a giant sea gorgon. A Mermaidusa. I mentioned years ago that I wanted gorgons to see more use and more variety again. Pay close attention when she uses her eye beams; her eyeballs aren't just popping out on stalks, which would be awesome enough for a mer person to be doing, but popping out in the mouths of two of her "snakes" as they curl around to apparently penetrate the back of her skull, and let's not forget that these snakes are simultaneously the tentacles of the octopus on her head.

This all kicks so much ass that we don't even need to end the battle by facing only a reptilian mermaid's floating, severed giant head, but this game is just the gift that keeps on giving, isn't it?