Cuphead and Mugman’s Toughest Bouts
Cuphead is best known for two things: its gorgeous hand-drawn animation, and its relentless difficulty. Studio MDHR’s debut release made a name for itself by combining the whimsical style of 1930s-era cartoons with the soul-crushing challenge of Dark Souls. It’s quite the combo.
While Cuphead includes six traditional platforming levels (a late but welcome addition during development), the real meat and potatoes are its boss fights. The game features a hellish gauntlet of 19 bosses for Cuphead and Mugman to conquer. Some are pushovers, but the majority are—consistent with Cuphead’s pedigree—tough as nails.
But which Cuphead baddie is the baddest? Let’s take a look at all 19 Cuphead bosses, ranked by difficulty.
Want to hop to a specific boss? Here’s a handy cheat sheet (in alphabetical order):
- Baroness Von Bon Bon
- Beppi The Clown
- Cagney Carnation
- Cala Maria
- Captain Brineybeard
- The Devil
- Djimmi The Great
- Dr. Kahl’s Robot
- Goopy Le Grande
- Grim Matchstick
- Hilda Berg
- King Dice
- Phantom Express
- Ribby and Croaks
- The Root Pack
- Rumor Honeybottoms
- Sally Stageplay
- Wally Warbles
- Werner Werman
How Difficult Is Cuphead?
The difficulty of Cuphead bosses comes down to a few factors: placement in the story, length and number of phases, RNG, rank, and difficulty level.
Placement in the Story
As you’d expect from a video game, Cuphead gets more difficult the farther in you get. That said, there are certain late-game bosses that pose little challenge for the average player. By then, you’ll be familiar with tactics like parrying. You’ll also have access to crucial items from Porkrind’s Emporium, like the Smoke Bomb charm, which grants invulnerability while dashing.
Length/Number of Phases
All bosses in Cuphead have different phases they go through, signified by a vertical black line on the retry screen. Bosses don’t have checkpoints, so the more phases they have, the longer and tougher the bout in general.
Boss RNG in Cuphead
When you’re fighting a boss with multiple phases, especially early on in Cuphead, you’re in for a tough go. Making things harder is the presence of RNG for certain bosses. These bosses will randomize their attacks, adding a layer of variance to the fight.
Cuphead Difficulty Levels
Cuphead has three difficulty levels: Simple, Regular, and Expert. Simple and Regular are available from the start, while Expert unlocks only after completing the game. These difficulties alter the phases of each boss; simple tends to remove phases, while Expert adds phases or makes existing ones trickier.
Tip: You cannot complete Cuphead on Simple. While Simple lets you progress through the game’s three Inkwell Isles (i.e., worlds), you can’t tackle the four and final world, Inkwell Hell, without beating all bosses on Regular. In this sense, Simple’s meant as more of a practice mode.
Cuphead also has a rank system, incentivizing players not just to beat these bosses, but to give them a real whooping too. These ranks range from D- to A+ on Regular difficulty, and from D- to S on Expert. Getting the top rank essentially requires being perfect in your attempt. This includes:
- Beating the boss within two minutes
- Parrying at least three pink projectiles
- Staying at or above three health
- Getting six playing cards’ worth of super meter
If it sounds difficult, that’s because it is. Only by mastering the ins and outs of these boss battles can you get top honors in Cuphead.
Cuphead Bosses Ranked by Difficulty
For this list, we’re ranking these bosses according to Regular mode difficulty, regardless of rank. (Expert is another ballgame entirely, and transforms seemingly easy fights into absolute nightmares. Don’t even get me started on S-ranks.)
Without further ado, let’s dive in (from easiest to hardest):
19. The Root Pack
Located just down the road from the Elder Kettle’s home, the Root Pack is likely the first boss you’ll encounter on your journey. As such, it serves as a simple—and easy—primer for future battles.
The Root Pack has three phases, each of which is dedicated to a different root vegetable. You start by dodging mouthfuls of dirt from a potato. Then, you have to clobber an emotional onion while avoiding its tears (morbid, we know). The action wraps with a brawl with a giant carrot, which attacks with a mix of psychic beams and mini-carrot projectiles.
It sounds complex, but the patterns are all fairly simple. After a few attempts to get your bearings, the Root Pack should fall without fail.
18. Goopy Le Grande
Goopy’s arguably just as easy as the Root Pack before him. The blue blob hops around, throwing out a punch at Cuphead every few jumps. Deal enough damage, and the blob grows in size, revealing three pink question marks you can parry to get behind him and continue the onslaught.
Continue to chip away, and Goopy will die. He’s not done yet, however, as his grave starts chasing Cuphead around the field. Thankfully, his moves are all well telegraphed, giving you ample time to prepare and react. Shoot the face on the grave enough times, and Goopy will bite the dust—this time for good.
Tip: This boss is a great choice when looking to land an S-rank on Expert difficulty for the “Put On a Show” Trophy/Achievement.
17. Cagney Carnation
Cagney’s another easy battle. This scrap has Cuphead hopping between the ground and three floating platforms. In Cagney’s first phase, the flower mixes up a pair of attacks: a headbutt and a seedling projectile. The headbutt has a long windup, and while the seedlings sprout into some annoying enemies, they’re easy to pick off from afar.
The flower’s second form eliminates the bottom row, as Cagney sprouts vines and begins to attack the platforms. Again, though, these attacks are easy enough to predict. Keep your cool, and the fight will be over in a jiffy.
Note: Cagney may be a pushover, but he has a toe-tapping bop of a boss theme.
16. Hilda Berg
The first shmup-style boss on the list, Hilda Berg is also the easiest one. Hilda may not be too tough, but she does make for a lengthy fight with several phases and attack variations.
Also consider the fact that you have to learn a new control scheme for Cuphead and Mugman. In the cockpit of a plane, you have access to different guns, super moves, and even the ability to shrink down to a faster, nimbler “mini-plane.”
All that said, once you do a few practice runs with Hilda Berg, you’ll settle into the rhythm and put this baddie away.
15. Sally Stageplay
Flavor-wise, Sally Stageplay is an awesome boss. The entire bout takes place in the form of, well, a stage play—lights, curtain, actors, and all. Yet while certainly enjoyable, Sally’s a joke in terms of difficulty.
You encounter Sally on Inkwell Isle Three—the third of Cuphead’s four worlds. That means you’ll likely have access to powerful charms like the Smoke Bomb, which adds frames of invincibility to your dash. Even without the added perks, she makes for an easy fight.
Sally stays stationary for most of the play, and her early attacks are slow and easily avoidable. Later on, she transforms into a god, Sephiroth-style. In fact, her attacks in this phase are preceded by a Final Fantasy-esque sign announcing the attack (one’s even named Meteor). While flashy, these moves give you ample time to prepare and react accordingly.
In short, Sally Stageplay won’t give you much trouble at all.
14. Ribby and Croaks
Dynamic duos always make for tough video game fights (just look at Dark Souls’ Ornstein and Smough). Ribby and Croaks are no exception. They’re by no means hair-pulling in terms of difficulty, but they do give Cuphead and Mugman a run for their money.
There’s a lot to contend with in this fight. For one, you’re facing off against two separate enemies, each with unique attack patterns. Croaks starts by summoning an army of fireflies to crowd your airspace, while Ribby sends a barrage of punches low to the ground. Dodging Ribby’s punches in particular can be tricky, especially if you don’t deal with the fireflies first.
Deal enough damage to the two (doesn’t matter who—they share a health bar), and they’ll split off to separate sides of the screen. Keep avoiding their attacks, and eventually they’ll combine into a slot machine—complete with a unique series of dangerous attacks.
This fight can be overwhelming at first, and requires some expert dodging and parrying knowledge. Once you get the hang of Ribby and Croaks’ attacks, though, you’ll make ‘em croak. I’ll leave.
Note: Expert difficulty transforms this fight from a semi-challenging bout into a real soul-crusher. If you’re looking for that Ornstein and Smough-level difficulty, look no further.
13. Djimmi The Great
Djimmi The Great makes for one of the best shmup bosses in Cuphead. He’s challenging, with multiple phases, some tricky side-scrolling, and plenty of bullet-hell shenanigans. But he’s fair, devoid of the frustrations that plague some of the later entries on this list.
Most of this fight is straightforward, with well-telegraphed attack patterns, and bullets you can (and should) parry to build up your super move bar. The trickiest segment has you weaving through oncoming pillars. Djimmi also tests your might in his final phase, having you duck as dark matter rays threaten to singe you to oblivion.
There’s not much else to this fight. Play it, enjoy it, and take in the awesome animation and music when you do so.
12. Baroness Von Bon Bon
Baroness Von Bon Bon offers a prelude to some of the tricker fights in Cuphead. She sits atop a castle of sweets, sending in her candy troops to do her bidding. There are several types of troops she can call upon, from a rolling peppermint candy to a gumball machine that shoots projectiles into the air.
While these individual candies aren’t super difficult, there are many to keep track of. The Baroness calls upon them randomly, so you need to stay on your toes if you want to make it through the fight unscathed.
Deal enough damage to her troops, and the Baroness transitions into her final phase. She commands her castle to chase you, forcing Cuphead and Mugman to retreat to the left and fire at her when able. Chip away slowly, and the candy noble will lick her wounds.
11. Werner Werman
As his name implies, Werner Werman is a military veteran. In his initial phase, he sends out a volley of bomb projectiles that are tough to avoid. He also sends out a pair of pink mousetraps, which you can parry to get behind the boss, a la Goopy Le Grande.
Initial phase aside, this boss is a straightforward fight. In his second phase, you must avoid some slow buzzsaws by hopping between two levels of the arena. Then, when Werner is comedically eaten by a cat, you have to avoid flying projectiles while popping away at the new baddie. The cat—and Werner—will fall soon enough.
Like Sally Stageplay, Werner shows up on Inkwell Isle Three. While not nearly as easy as his peer, he’s a walk in the park compared to the other bosses lying in wait.
10. Cala Maria
Cala Maria is another enjoyable shmup fight, though not without some frustrations. Like Djimmi, she has several types of attacks, most of which are challenging without feeling overwhelming. The exception is a series of ghosts she sends toward the player. The attack can feel impossible to avoid, but a quick switch to the mini-plane gives you enough speed to evade.
Cala Maria also likes to turn Cuphead and Mugman to stone with her medusa’s gaze. You can escape from this paralysis by flicking the switch rapidly, but you’ll be vulnerable for a second or two. This isn’t much of an issue until the final phase of the fight, when you must navigate a tight corridor lined with spikes. Get hit with her gaze here, and you’re pretty much guaranteed to lose health.
Once you get comfortable avoiding the ghosts and gaze, Cala Maria becomes a much more manageable fight.
9. Captain Brineybeard
Captain Brineybeard is a suffocating fight. While no one attack is obscenely difficult to avoid, the pirate throws so much at you at once that it can be hard to stay afloat.
This grand slam has a bit of everything. Stay in one spot too long, and a barrel slams down on you from above. Meanwhile, a squid shoots ink projectiles into the air, a shark dives across the screen, and Brineybeard pops off shots from his ship. Heck, even the ship has an attack, spitting a cannonball your way.
And that’s just the first phase. Do enough damage amid the madness, and the ship turns into a hulking monstrosity. Dodge the spinning projectiles it sends your way, get some good shots in at its tongue, and the boss will finally—finally—fall.
8. Wally Warbles
This is where the fights start to get difficult. Another shmup boss, Wally Warbles has multiple phases, all of which are challenging. You have to dodge flying eggs, bullets, feathers, and even a procession of chiclets.
Then, when presumably near death, Wally’s heart pops out of the bird’s chest, leading to a new phase with even more flying objects to dodge. The fight isn’t terribly long, but it definitely takes time to learn and master.
Tip: Even during shmup segments, remember to swap between weapons. Cuphead and Mugman have a bomb lob attack that’s especially useful during Wally’s final phase, when he’s on a stretcher that’s hard to hit.
7. Phantom Express
Phantom Express can be extremely challenging unless you’re properly equipped for the fight. Most bosses in Cuphead are best tackled with the Smoke Bomb charm. For the Express, though, we suggest swapping over to the P. Sugar charm, which lets you auto-parry.
The reason: In this fight, Cuphead and Mugman drive a rolling cart, controlled by parrying the valves on either side. In addition, the Phantom Express sends out flying bricks that will hit the valves, sending the cart hurtling one way or the other. You can parry the bricks to protect the cart, but between both the valves and the bricks, this makes for a lot to remember.
With P. Sugar equipped, you can let the charm do the heavy lifting while you whittle away at the train’s health. Also make sure you have the Spread gun in your arsenal, for when you’re up close and personal with the Express.
Even with the right kit, the Phantom Express can be a headache. The Express begins as a ghost, shooting out large eyeballs that can easily strip away your health. Thankfully, the train’s next two phases are fairly predictable. Get comfortable with the first few minutes, and the rest of the fight should pose far less trouble.
6. Beppi The Clown
Beppi’s a crafty fella. Located at the carnival on Inkwell Isle Two, this clown hits far above his pay grade, outclassing many of the bosses located on the subsequent island. That’s half of why he’s so high on this list. The other 50% is sheer RNG madness.
Each of Beppi The Clown’s phases rely heavily on blind luck (or misfortune, depending on your outlook). First, he tries to ram a bumper car into you. As you hop over him, flying ducks holding dangerous light bulbs serve as a deterrent to crowd the air.
Next, Beppi blows up a series of floating dog heads to chomp at you. Meanwhile, a roller-coaster cart speeds toward you, threatening to flatten you. Other attacks include flying horseshoes, floating baseballs, and some penguins for good measure.
Each of Beppi’s phases is tricky in its own right. Throw them all together, and you get a true carnival of horrors.
5. King Dice
Now we’re getting to some wicked baddies. King Dice is the penultimate boss in Cuphead. He’s the final roadblock on your journey to find the Devil. And he certainly makes you work to meet the big bossman.
King Dice is a unique boss, in that he does very little of the actual fighting. Instead, he throws Cuphead and Mugman through a gauntlet of mini-bosses, culminating in a final faceoff with Dice himself. It’s basically a boss-rush within a boss-rush. Cuphead-ception.
Individually, these mini-bosses aren’t too challenging. They tend to have one to two attacks each, making them easy to master. The problem is, there are nine of them. And you have to beat them in succession, then Dice himself, with zero checkpoints.
Here’s the good news: You don’t have to fight all nine. You begin the sequence by parrying a pink die, which rolls either a one, a two, or a three. The result moves you across a craps table, from “Start” on the far left to “Fin” on the far right. Time the rolls correctly, and you can reach King Dice by fighting only three mini-bosses.
Memorize the bosses, time the rolls, and you’ll breeze through to King Dice. Beware, though: Dice’s sequence involves some serious parrying. Make sure you gather as many bonus hearts as you can from the board before you take him on.
4. Grim Matchstick
Grim Matchstick is a juggernaut of a boss. Another Inkwell Isle Two baddie, this dragon doesn’t bother with crazy transformations. It lets its fire do the talking.
The first phase of this melee is surprisingly straightforward. The bout has you hopping between clouds to dodge both psychic beams and fiery meteors. From there, the action quickly heats up. Matchstick lays out its tongue, red carpet style, and tiny sparks of fires strut across the screen. Unfortunately, these sparks also fly at you—and at alarming speed.
The trick to this phase is to watch the positioning of the sparks. If they’re facing away from your character, you can stay put; if you’re in their sights, you better move. Quickly.
Grim Matchstick’s final phase sees the dragon spawn two additional heads. Each head takes turns firing off orbs of fire that, if hit by your bullets, multiply into even smaller projectiles. Making matters worse, the heads breathe lines of fire that can catch you by surprise if you’re not paying attention.
The only way to best Grim Matchstick is to stay vigilant. Pay attention to the dragon’s subtle tells, and don’t shoot willy-nilly during that last phase, lest you want to get smoked.
3. Dr. Kahl’s Robot
Dr. Kahl’s Robot is the worst shmup fight in Cuphead. Full stop. Unlike Djimmi The Great and Cala Maria, which are challenging but fair, this robot throws scruples right out the window.
On paper, Dr. Kahl’s Robot shows promise. Cuphead and Mugman must destroy each of the robot’s three weapons—a rotating beam on its head, a chest cannon, and a dock for Galaga-like ships in its belly. Avoiding these attacks while disabling them is challenging enough, but here’s the rub: Take one out, and it’s replaced with an even stronger variant.
The beam on its head? Bust it up, and Dr. Kahl’s Robot opens its mouth to shoot a spread of bullets. That Galaga dock? Mangle it, and Dr. Kahl’s Robot shoots out homing missiles with a massive hit radius upon detonation.
The exception is the robot’s chest. Destroy that weapon, and eventually the machine’s heart appears. Pepper that with bullets, and you proceed to the final stage of the battle—a face-off with Dr. Kahl himself. And wow, is it a doozy.
The doc gives you a bullet-hell sequence to end all bullet-hell sequences. As you weave around a series of moving obstacles, Kahl litters the screen with a spread of bullets. Considering you likely lost health prior to this point, it’s a miracle if you make it to the end in one piece. The battle’s intense, it’s overwhelming, and it’s tough. Like, really tough.
2. Rumor Honeybottoms
Rumor Honeybottoms is the one boss in Cuphead that feels unfair. The queen bee’s first phase isn’t too difficult, with a worker bee setting bombs that detonate and set off a circle of spikes. Unfortunately, due to the platform-heavy nature of the map, it’s tough to parry this attack, limiting your movement options.
It’s the next two phases that make this an agonizing fight. Rumor Honeybottoms shows up and starts cycling between three attacks: One, a pair of purple spheres that hover around the screen. Two, rotating triangles that shoot projectiles from their corners. Three, Bullet Bill-inspired bees that zigzag in an S shape. The latter two attacks are particularly irksome, requiring deft platforming while avoiding the red-hot honey below.
Make it to the final phase, and Honeybottoms turns into an airplane. She shoots homing fists your way, and also makes an occasional haymaker punch (with a chainsaw) that can easily catch you off-guard.
Similar to Grim Matchstick, the only tactic here is to pay close attention to the small tells. Aside from that, pray to RNGesus that Honeybottoms goes easy on you.
1. The Devil
The Devil lives up to his reputation. He’s a fearsome opponent, and the perfect fight to cap off a playthrough of Cuphead.
His fight is tricky in large part because it’s long. The first segment has Cuphead and Mugman evade a series of simple but incessant attacks that wear on the psyche. Throw in obnoxious imps that stroll through like they’re extras in a movie, and the Devil tests all the skills and reflexes you’ve honed on your journey.
Pepper the Devil with enough bullets, and he ditches his skin and dives into the bowels of hell. Follow him, and you transition to a segment with flying platforms, ghost axes, falling poker chips, and bombs that detonate unless you parry them. All told, this portion isn’t too tricky, but there’s still more to go.
In a third phase, the Devil turns up the heat, reducing the number of platforms and adding flying minions to the mix. This section serves as a bit of bullet hell in its own right, and it tests your mettle to get through it with health in the tank.
To close, the Devil destroys all platforms, save for one, and starts crying. Similar to that onion in the Root Pack, the tears will damage you, so you have to either parry them or time your jumps so you can dodge the falling debris and get those last few bullets in.
It may sound like a quick bout, but it’s anything but. The Devil makes you work for that credit roll, but it’s one hell of a ride, and a fitting finish for a game as challenging as Cuphead.
And that’s that! Enjoy the list? Share your thoughts in the comments below.
For more on Cuphead, head to our article on Cuphead’s animation.