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That One Boss / Cuphead

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Base game:

  • Baroness Von Bon Bon is arguably the point where the game stops messing around and starts killing you hard.
    • She sends out her minions at random, whose attacks are difficult to read and can home in on you, not to mention those awful little jellybean soldiers that dash out from the gates and are nearly impossible to notice against the rest of the chaos onscreen. And her final phase, while more predictable, is quite brutal as well due to that damnable homing head of hers chasing you everywhere.note 
    • Out of all the Baroness' courtiers, the jawbreaker is probably the deadliest to underestimate. It's not the fastest or the flashiest indeed, it's easily the slowest, and it has no projectiles to speak of but it's also the only one that unerringly homes in on you, and its slowness makes it much harder to smoke-bomb through (contrast the much-dreaded candy corn, which almost becomes a Zero-Effort Boss to someone who's mastered smoke-bombing). Worst of all, though, it's technically a Dual Boss a smaller "satellite" jawbreaker revolves around it, and while it can't directly home in on you, it is immune to all of your attacks. On Expert, there are two of these. And if you get the jawbreaker as the third phase of the fight, you get to deal with jellybean soldiers and the Baroness taking potshots at you with her peppermint gun on top of that.
    • Considering that the challenge provided by the Baroness' minions varies by the minion and when they are summoned with the first phase being uncomplicated and only consisting of fighting a minion, with the next two phases adding the jellybean soldiers and then a gunshot from the Baroness fighting the Baroness can be something of a Luck-Based Mission, with victory being easier if the Random Number God doesn't send out the minion you most dread at the worst time.
  • Grim Matchstick's second and third phases: the fireball imp things that leap up at random would already be difficult to navigate without trying to stay on the constantly-moving clouds and turn around for an attack on the boss, though the homing shots can cut down the hassle slightly by letting you damage the boss and put focus on dodging the imps without worrying too much about your footing. The same cannot be said of Matchstick's third phase, with the first appearance of the widely despised fire bubbles. They're slow-moving, and yet somehow incredibly difficult to dodge, and act as a counter for the aforementioned homing attacks by drawing them in like flares. To make matters worse, every so often Matchstick breathes fire and cuts off the entire center of the stage, severely limiting your movements.
    • Ironically, the second and third phases are actually a bit easier on Expert, because the screen scrolls in the opposite direction. For the second and third phases, this means the screen is moving you away from Matchstick as opposed to normal where it's moving you towards him, making it easier to keep your distance from him while you attack. For the second phase, this makes dodging the fire imps less of a pain since you don't have to divide your attention between them and ensuring you're not getting too close to Matchstick while you attack. For the third phase, this makes the platforming easier because the reversed scrolling makes the clouds appear from the left side of the screen as opposed to the right side, and since you are primarily on the right side of the screen during this phase, this means you have a little more time to plan your trajectory before you have to move as you no longer have the threat of Matchstick catching you if you wait too long; and again, this makes it easier for you to focus on dodging Matchstick's attacks.
  • Expert buffs Wally Warbles into this trope for the plane levels. This is the point where Bullet Hell really kicks in; the first phase removes the strategy of hugging the left side by adding two egg shards that shoot into the left side, turning what boiled down to pressing up and down to follow the boss to being forced to stay up in his face to keep pumping constant damage into him and reacting fast to the other egg shards. Willy and his egg barricade in the second phase is basically a check to make sure you understand when to switch between guns and bombs and have learned how to use the shrink move to get out of tight spots. The final phase challenges you to keep track of three separate sources of erratic projectiles while returning fire; the trash attack in particular is incredibly hard to maneuverer around if Wally's stretcher happens to be on the left side of the screen.
  • Rumor Honeybottoms forces you to continuously get away from death coming from a rising floor in addition to avoiding a swarm of enemies. And once the enemies stop, the big projectiles with irregular patterns begin, making constant movement necessary and making it quite easy to get caught in a painful dead end. The platforms available to jump on furthermore come in random patterns, which can become horribly inconvenient if you have to dodge a certain way and there are little to no platforms for you to jump for. Coupled with the need to keep moving up and the large amounts of space a lot of her attacks cover, the fight sometimes devolves into a Luck-Based Mission. Bringing Parry Sugar will make it much more manageable, by way of making her most vicious spellcraft during the second phase a lot easier to handle; just remember never to parry anything from below the actual spell, you'll take that hit anyway if you do.
  • Dr. Kahl's Robot makes Wally Warbles' Bullet Hell look like a cakewalk. While its patterns are predictable, those patterns are a lot to deal with; no boss in the game fills the screen like this one. First, you have to break off segments of the robot, and each time you do, it gets a new attack to worry about, including ones that come from behind. Then you have to strike its head while homing missiles pester you with a rather large blast radius, and finally you have to navigate a seemingly endless barrage of bullets (many of which are pink and now parryable in the patched version, thank goodness) that cover the screen while avoiding walls. Good luck even making it to the last phase with all your HP intact.
  • Of the King's Court bosses in King Dice's fight:
    • Everybody seems to dread Phear Lap the most due to a major case of Obstructive Foreground caused by all the dead trees in the stage, which is absolutely horrible for a Shoot 'Em Up sequence since it leads to some nasty Interface Screw. That, and the hooded jockeys that leap at you from below are too damned fast (if you're close and aren't currently pressing down the Dodge button, kiss one HP goodbye) and are obstructed really often by the aforementioned dead trees.
    • The Tipsy Troop isn't well liked either. You'd think that being number one on the list, they'd be the easiest, right? On the contrary. They're one of the hardest of the bunch, mostly due to the fact that there are three of them. One of them fires homing olives at you while the other two throw out waves of alcohol either on the ground or falling vertically from the sky. While they're easy to dodge by themselves, the fact that you're usually dealing with several attacks one right after the other makes them unusually hard for one of the bosses of the King's Court.
    • Mr. Chimes is the last boss in the King's Court for a reason. Most people dread accidentally hitting his section and having to fight him. Unless you are exceptionally good at memory games, he is worse than even Phear Lap. His projectiles are easy to dodge, but his movement speed gets crazy if you mess up the card matching, and even in the best-case scenario, the fight is more time-consuming than that of any other miniboss.

The Delicious Last Course:

  • Besides the final one, Esther Winchester is generally considered the hardest of the DLC bosses; multiple comments on any video with her will compare her directly to Dr. Kahl's Robot. The main culprit is the sheer Bullet Hell of her first and third phases. What separates her from Dr. Kahl's Robot is that her projectiles have strange patterns that take getting used to and she switches positions on the screen to further confuse you. This is followed with the sausage strings in her final phase, which cover the stage and have to be dodged by passing through their gaps while also avoiding the constant blasts of chili peppers coming from the sausage tin.
  • Glumstone the Giant is usually considered the hardest platformer boss for The Delicious Last Course. The first phase of the fight is absolute chaos despite Glumstone's massive size making him easy to hit, as his gnomes attack from many places and serve as Spikes of Doom that force you onto thin platforms that rise and fall. He has his own attacks as well, with his geese crossing attack being the worst (coming out almost instantly after he blows his nose and taking up the upper half of the screen for a few seconds, and the platforms can raise you right into it). The second phase is much easier, aside from the jumping gnomes being hard to notice at times. The final phase picks things back up with an awkward moving target to hit, plenty of projectiles in a narrow area, and platforms over an acid pit that gradually vanish and need to be called back up with parries.
  • Mortimer Freeze goes from being a relatively okay boss in Regular mode to an absolute challenge in Expert mode, especially if one's trying to aim for an S-rank. Between his sporadic parry chances, his more erratic aiming for his icicles in the first phase, his faster move mix-ups in the second phase (combined with his sword attack being upgraded from obstacles you need to watch your positioning of to a wave of swords that you have to dash over), and his eyeball attack in his final phase having an increased fire rate (meaning that it's a lot harder to navigate around on the spinning platforms when he fires it), as well as having one of the highest HP values of a non-final platformer boss in the entire game, he's frequently cited as having one of the most drastic difficulty spikes between difficulty modes of any boss in the game.
  • Out of King's Champions, The Knight is generally considered the toughest and most annoying, despite being only the second miniboss. His moveset is relentlessly fast and unpredictable (And he will never expose himself if don't get close enough), one of them being a screen-splitting lunge and another being an enormous slash that reaches almost the other side of the boss arena. The worst is an attack that leaves only a split second open window for the boss' weak spot, thus making the player's health even more vulnerable. On top of it all, The Knight has a tendency to taunt and wait for an opening to attack and he has the highest health pool out of all the champions note , thus making the boss fight against him far longer. It's also certainly not helped by how he is by and far the least interesting of the bosses, being faced in a very generic arena with very basic attacks, and the only thing he does between attacks is stumble back and forth, so he lacks the comedic elements and memorable quirks the other champions have.