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  • Alternative Character Interpretation: It's hard to tell with the bosses since all you do is fight them, but not all of them seem inherently evil. After all, Cuphead and Mugman lose their souls to the Devil and aren't evil. At least, some of the debtors probably aren't evil, but they are none too keen to lose their souls so all of them resolve to go down fighting.
  • Anti-Climax Boss:
    • King Dice himself is already pretty easy to counter attack, seeing as the player has likely mastered parrying at that point. It's justified, as the Boss Bonanza beforehand was the main draw of the fight. But if you realize that the gap between his hands and the wall is juuuuuuuust big enough for Cuphead to fit...
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    • The Devil's last phase is just you shooting at the guy's face while he cries. If you survived the previous phases with more than one hit left, you don't even need to dodge at this point unless you're going for a perfect rank.
  • Author's Saving Throw: The 1.2 update makes Mugman finally playable in single player mode like Cuphead instead of being restricted to being a co-op-only character.
  • Awesome Art: Easily one of the main selling points of this games. Everything in the world of Cuphead was traditionally hand-drawn in order to capture the feel of old school cartoons akin to Fleischer studios, and the dedication certainly shows. The backgrounds in each level look absolutely stunning and the characters are extremely well animated, allowing them to stand out alongside the scenery as well as among the chaos onscreen.
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  • Awesome Bosses: Many bosses have become notable with fans for one reason or another (Werner, Wally, Phantom Express, etc), but King Dice is usually the most fondly remembered thanks to his fight pitting you up against multiple mini-bosses before finally facing him.
  • Awesomeness Withdrawal: The length of the game varies depending on one's skill with the game, but the average playthrough lasts around 4-5 hours. And considering the unique and impressive boss fights and animation, it has led to at least some reviewers lamenting there wasn't more content.
  • Breather Boss:
    • Sally Stageplay is less stressful to fight compared to some of the earlier bosses. Keep in mind, she can still be tricky to beat, but her attacks are easier to read and not quite as chaotic as the Bullet Hell of some of the other bosses. Perhaps fittingly, her fight is more comical compared to the Nightmare Fuel in the earlier boss battles, and her final phase is arguably the most mundane in the game.
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    • Werner Werman also counts too, as most of the attacks in his phases are easier to dodge and are can be easily telegraphed compared to some of the other bosses in his world. Akin to Sally, the overall tone of his battle is more comical as a result.
    • Captain Brineybeard's attacks are very easily telegraphed, the barrel at the top is invulnerable but only comes straight down, and there is significantly less on-screen action when compared to Rumor Honeybottoms or Cala Maria. Even the final phase, while having unusually moving projectiles, has very little health when compared to others. True, there are a ton of simultaneous threats even if each one's simple, the last phase can easily pincer you into an inescapable situation between barrel and Breath Weapon, and on his own he'd likely qualify as average or even That One Boss. But considering his specific location, with Honeybottoms being the only other available path and right after the infamous Difficulty Spike that is Grim Matchstick, his battle comes off as outright restful.
    • The Phantom Express isn't as difficult as it looks, especially if you know that you can dodge most of its attacks by staying in certain spots on the screen. Even without this knowledge, staying on top isn't too hard as long as you can parry decently, and having Parry Sugar neuters most of the constant dangers of the stage.
    • From the King's Court, both Hopus Pocus and Pirouletta are incredibly easy to beat if you have the Smoke Bomb equipped. Hopus Pocus' skull attack can easily be bypassed just by dashing through it, and the horizontal line of projectiles he sends at you is easily beaten with a parry. Both of Pirouletta's moves are easily dodged via dash, as her rain of roulette balls can be dashed through easily, and as long as you don't dash too early, you can easily dash through her legs when she is dancing across the screen. Mangosteen is also very simple, as he's a Stationary Boss with a very easily dodged attack; just stay away from the edges of the screen to avoid being ganked by a sudden chalk cube, and you should be alright.
  • Broken Base: The decision to have the game remain exclusive to Xbox One and PC until further notice. Is it a smart idea that lets Microsoft have another game license of its own, or should it also be released on other platforms so that their followers can get a chance to play it? Of particular contention was the original intent to release on other platforms, then Microsoft essentially bought the whole thing out from under everyone else. While the additional cash did allow for the immense content expansion into the final game, many were still disappointed.
    • Mitigated by the fact that the PC Windows version isn't exclusive to Windows Store (in fact, it's also available on Steam and GOG), allowing Windows 7, Windows 8, Windows 8.1, and non-Store using Windows 10 users to buy and play the game. Even more when the game was later released for Mac and Nintendo Switch.
  • Critical Dissonance: While both critics and fans have high praise for the game, they seem to be split on the quality of a certain boss fight (the randomized Boss Bonanza against King Dice) towards the end of the game. Critics panned it as a Disappointing Last Level that reveled in the type of Fake Difficulty that the game had avoided until that point. Fans, however, have really taken to it, treating King Dice as an Ensemble Dark Horse and praising the fight as an excellent Climax Boss and a great lead-up to the Devil himself, pointing out that the randomized nature of the fight fits into the anti-gambling themes of the game. (It's also not actually random — you can go exactly where you want with good timing. The bonus HP hearts are randomly placed, though.)
  • Crosses the Line Twice:
    • During the Boss Battle with Goopy, you don't just fight him. You also fight his tombstone. It can move around and smack you flat.
    • When fighting against the giant cuckoo clock bird Wally Warbles: Once defeated, he will become knocked out and featherless, then his son, a chick with psychic powers, will fight you instead. After defeating the chick, Wally appears again, now featherless and lying on a stretcher carried by two smaller blue birds that aid him in the battle. Once Wally is defeated again, the blue birds choose to prepare to cook and eat him, salting and peppering his body.
    • The curtain in Sally Stageplay's fight proudly displays that it's made of asbestos. A post-launch update also lets you stand on some cherubs to drop a light fixture on Sally's husband, crushing him to death.
    • The Macintosh Launch Trailer is a short involving a character with an apple for a head coming across Cuphead and Mugman happily eating apples from a nearby tree. When the Applehead sees this, he understandably freaks out. Cupheadnote  sees this freak-out, hesitantly swallows his bite, and sheepishly puts the apple away. Mugmannote ? He happily keeps eating with no care in the world.
      • However, Mugman may have simply been staring off into space, meaning he didn't even realize Mr. Apple Guy was there. Still freaky, though.
  • Crossover Ship: Cuphead and Bendy, which has enough of a following to the point where it borders on Fan-Preferred Couple. See Friendly Fandoms below.
  • Designated Villain: In an amazing example of irony, the Devil himself is this for some. Though a minority, a nonetheless considerable number of fans argues that the Devil, while not a good guy by any stretch of the imagination, is actually a Necessary Evil in the context of the story. Since the Inkwell Isles folks you fight against all willingly signed a Soul Contract and sold their souls to the Prince of Darkness himself, it makes all of them not particularly good people, and in trying to avoid the consequences of their actions, earning something out of their deals and paying nothing in return, they are effectively Karma Houdinis...Except for the fact that what Cuphead And Mugman did to the Runaway Debtors before challenging the Devil is them being on the receiving end of Break the Haughty.
  • Ear Worm: "Don't Deal with the Devil" (a.k.a. the title screen theme) is easy to get stuck in one's head due to how catchy it is.
  • Ensemble Dark Horse:
    • Despite being a very difficult boss to many, plenty of people have been slowly growing attached to Grim Matchstick. The general consensus is that he's too adorable to stay angry at, and is generally beloved despite the rage he induces. Helping matters is the fact that his death quotes are very sweet and apologetic as opposed to the taunts of most of the other bosses.
    • Cagney Carnation was one of the first bosses seen from the game, leading to him having a place in many players' hearts. The general Body Horror he pulls off during his fight (such as his many twisted facial expressions), the lively background music of the stage, and the fact that his fight is where the game's difficulty really starts picking up really help him make a good first impression.
    • Cala Maria is another extremely popular boss, mainly among a certain part of the fandom thanks to her attractive design.
    • Mac and Lord Forkington are both NPCs who only pop up on the Inkwell Isle map, but they do receive quite a bit of attention.
  • Evil Is Cool:
    • King Dice, credited to his great design, Boss Bonanza boss fight, and his very catchy Villain Song.
    • Don't forget The Devil himself; he spends most of the game with a smug grin which gives the impression that he always wins in the end, and he knows it.
  • Evil Is Sexy: Cala Maria, in both forms according to the fans and especially the fanart. See Ensemble Dark Horse for more details.
  • Family-Unfriendly Aesop: At the end of the game, you welch on a deal, beat your creditor into submission, and then set all his debtors, who all tried to kill you, free. And everyone loves you.
  • Fanon:
    • It's widely accepted that the Devil is always portrayed without clothes because his layer of fur causes him to dislike them. In addition, many fans have taken to comparing Old Scratch to a cat, complete with purring and enjoying getting his fur scratched.
    • Fans of the bad ending versions of Cuphead and Mugman often depict them as the Devil's adopted sons in fanart (and occasionally King Dice's too).
    • Grim Matchstick made his Soul Contract because he was lonely.
    • Humanizations of King Dice tend to favor towards portraying him as black, due to his inspirations from Cab Calloway and Louis Armstrong.
    • While Cuphead and Mugman look relatively the same in-game, fanart tends to make Mugman leaner with a thinner cup for a head, usually due to the comparisons to another certain duo. Likewise, it's generally agreed that Cuphead is the older brother and Mugman is the younger brother.
    • Fans also like to assume that Mugman speaks with a very friendly southern drawl, like Jack McBrayer's.
    • Baroness von Bon Bon and Beppi the Clown are shown a lot together as Vitriolic Best Buds. Djimmi the Great is also usually thrown into the mix to make them a Power Trio.
    • With his mad scientist look, status of That One Boss, and not showing up in the ending, some people have gone with the interpretation that Dr. Kahl is the only legitimately evil/villainous debtor.
    • Hilda Berg and Cagney Carnation are often portrayed as close, potentially childhood friends, and sometimes even lovers.
    • When it comes to crossovers with Bendy and the Ink Machine, it's quite common to feature Cuphead and Mugman not getting along with Bendy due to the similarities between their respective games (despite being in Friendly Fandoms).
    • Because of him being a flower, it is widely belived that Cagney Carnation hates winter and will spend it inside.
  • Fanfic Fuel: What the various debtors made their Soul Contracts with the Devil for and why they did so is becoming a common fanfiction magnet.
  • Fan-Preferred Couple:
    • An overwhelming amount of fans sees the Devil and King Dice as an Unholy Matrimony.
    • A lot of fans ship Cuphead and Baroness Von Bon Bon along with Mugman and Cala Maria.
    • Cuphead or Mugman/Legendary Chalice was popular enough, but with the announcement of the Delicious Last Course DLC, Cuphead or Mugman/Ms. Chalice exploded overnight.
  • Foe Yay: Cala Maria gloating when she causes the boys to die involves some flirting, about whether or not to "release" them.
  • Fridge Logic: Fight a giant robot in a junkyard; You use a plane. Fight a mermaid in the ocean; You use a plane. Fight a dragon flying in the sky; You don't use a plane.
  • Friendly Fandoms: With Bendy and the Ink Machine, since both games have an old-timey cartoon aestheticnote . Heck, the third episode of that series was released right on the eve of Cuphead's release date.
  • Game-Breaker:
    • The charge shot weapon used to deal an absurd amount of damage relative to the time needed to charge it to full strength, making it a very effective weapon in most situations. It was so overpowered that the developers nerfed it in a patch to deal with it.
    • Some of the bosses have massive, screen-sized attacks that need to be avoided in a certain way (like Sally Stageplay's wave that you need to parry a pink star to avoid). You could dodge them in the intended ways, or you could use the Smoke Bomb dash to cheese them.
    • If you bring in the Lobber and Roundabout weapons into a platformer fight, you can overcome their low fire rate by rapidly switching between the two, dealing massive damage to bosses in the process. This was removed in a later patch.
  • Genius Bonus:
    • The name of the level "Murine Corps", where you fight the rat Werner Werman. It seems like a simple play on "Marine Corps", but "murine" is an adjective that describes something rodentlike or related to rodents.
    • The constellations that Hilda Berg uses to telegraph some of her attacks are not random; astronomy buffs should notice that they are faithful replicas of the actual zodiac constellations (and the form she takes indeed reflects that).
  • Germans Love David Hasselhoff: There are various fan artists all the way over in Asia (mostly Japan and Korea), as you can see from Twitter, Pixv, and Tumblr.
  • Goddamned Bats: The fish in Perilous Piers die quickly and have a predictable pattern, but they're everywhere and they appear randomly at random heights.
  • Good Bad Bugs: Though many of these bugs were dealt with in a later patch, this list compiles the bugs that were available in the previous version of the game.
    • You can end the fight against Mr. Chimes almost immediately by forcing him to clip out of the arena.
    • "Fresh Expert". After the game is cleared on any save file, you can set the difficulty to Expert, quit to the main menu, and either load another file or start a new one, and the difficulty selector will remember it's set to Expert. The selection appears as a blank space, but still works, allowing Expert clears and S-ranks to be earned right away.
    • By rapidly alternating between the Lobber and Roundabout shots, you can exploit a glitch with most of the bosses' hitboxes to cut down their health at a stupidly fast rate. Gleefully abused by the Hobo Bros here.
    • By standing just on the edge of the hole that leads to its second phase (so that the wall of flame doesn't reach you) and then firing the Charge weapon repeatedly, the second (and arguably more difficult) half of the Final Boss easily becomes a Zero-Effort Boss (demonstrated here).
    • Pulling the first Super on King Dice, while he's marching out the cards, can turn him into a Zero-Effort Boss. (Don't rely on this to help you get an A- or S-rank, though — it only kicks in if he decides to use the same hand twice in a row, which is very rare.)
    • And for the finale, there was the infamous Mugman glitch where you click "Remove Player 2" and get another Mugman.
  • Heartwarming in Hindsight: Due to an accidental case of Reality Subtext, Chad and Jared Moldenhauer having to mortgage their homes and risk everything to make this game a success mirrors Cuphead and Mugman's struggle. The game going platinum in just two weeks surely reflects on the story's good ending, too.
  • Hilarious in Hindsight:
    • Devil May Cry 4 had That One Level where you had to play a board game by hitting a die, with a random chance of either fighting enemies or a previous boss, which fans hated. Cuphead used a similar mechanic for a boss fight several years later, which fans really like.
    • This comic, created months before the game's release, features a disgruntled Cuphead calling Bendy "Let's Play trash", due to how popular Bendy's game was with Let's Players. Come the release of Cuphead's game, it too became a favorite among Let's Players. Spoke a little too soon, huh, Cuphead?
  • "Holy Shit!" Quotient: A possible two-in-a-row for Murine Corps. The first comes when the boss, Werner Werman, is eaten by the cat behind the wall, who then breaks it and fills the screen. Even if the background hints clued you in to this, you will most likely be stunned when it actually happens. The second, completely unexpected occurrence arrives when you actually beat the boss: It's revealed that the cat was a mechanical one, and Werner was controlling it through a cockpit in its head the entire time it was on-screen. You magnificent trooper, Werner.
    • This can be an usual reaction for any beginner that has defeated Goopy Le Grande in the second stage and never expected that the battle still continues with his gravestone attacking you.
  • Idiosyncratic Ship Naming:
    • Snake Eyes = The Devil/King Dice
    • Ghost Blossom = Cagney Carnation/Blind Specter
    • Melon Candy = Grim Matchstick/Baroness Von Bon Bon
    • Starry Flower = Hilda Berg/Cagney Carnation
    • Magical Carnival = Djimmi The Great/Beppi The Clown
    • Smokey Roulette = Mr. Wheezy/Pirouletta
    • Cupcest = Cuphead/Mugman
    • Lab Rat = Dr. Kahl/Werner Werman
    • Pollination = Cagney Carnation/Rumor Honeybottoms
  • Idiot Plot: Tropes Are Not Bad, however. The whole plot starts because Cuphead was greedy enough to take the Devil's high-stakes bet, risking his and Mugman's souls against the casino's winnings. It also gets lampshaded by Elder Kettle, and Mugman is less than amused that his brother didn't listen.
  • Incest Yay Shipping: Some fans can often ship Cuphead and Mugman with each other in art (they are brothers, after all), putting the Ho Yay meaning to the term "brotherly love". Combined with the fact that they have Vague Ages, it's possible that they just started puberty, which can make their relationship with each other a little more... suggestive.
  • It's Hard, So It Sucks!: Averted. Cuphead has Metacritic aggregate scores of 88 and 86 on PC and Xbox One, respectively. Many reviews have praised the game for its Nintendo Hard difficulty.
  • It's Popular, Now It Sucks!: Along with other Indie Video Games becoming mainstream, this game has been criticized for its sudden rise in popularity on the Internet.
  • Les Yay: In the fight against Ribby and Croaks, while most of the background characters are observing the fight, one ladybug is too busy staring dreamily at the dancing showgirls.
  • Love to Hate: King Dice for his Evil Is Cool status, his catchy Villain Song, and his creative boss fight.
  • Memetic Loser: To an extent, Captain Brineybeard. His battle is one of the more forgettable ones, he's Overshadowed by Awesome by most of the other bosses (including fellow human bosses Badass Normal Sally Stageplay and That One Boss Dr. Kahl), and he's the one boss in the game who doesn't even get to fight in the last phase of his own battle, getting upstaged by his own ship in a rather humiliating manner.
  • Memetic Mutation:
    • The cylinder.Explanation 
    • It's Just like Dark Souls. Explanation 
    • Friendly reminder that King Dice has already fucked your wife.Explanation 
    • Cuphead and his pal Mugman, and his pal Mugman, and his pal Mugman, and his pal Mugman... Explanation 
    • Goopy le Grande is dead.Explanation 
    • "The person below triple gay" Explanation 
    • "Good day for a swell battle!"
    • Cuphead confirmed for Smash. Explanation 
    • Cuckhead and his pal Fuckman Explanation 
  • Moe:
    • Suffice to say, Cuphead and Mugman themselves are adorable.
    • Among the bosses, Weepy is the main example for obvious reasons.
    • Ms. Chalice is also very cute, both as a ghost and as a playable character.
  • Most Annoying Sound:
  • Most Wonderful Sound:
    • The sound that occurs when Cuphead or Mugman is revived. "Thank you!"
    • When you use the missile attack, and connect with the enemy in a massive satisfying "BOOM!"
    • The little fanfare that comes with beating a boss on the map screen. "Cup-heeeead!"
    • The slap sound when you parry an attack.
    • "Knockout!" (When you defeat a boss) / "Bravo!" (When you complete a run n' gun level) / "Victory!" (When you beat a Mausoleum)
    • On a somewhat weird note, quite a few people thought that the "apple crunch" sound from the Crispy Apples short was very satisfying to hear. Some even compared it to ASMR.
  • Never Live It Down: Venturebeat got a metric ton of flak for their showcase of the 2017 E3 press demo. The reporter couldn't even get through the opening tutorial. They would later be the butt of a lot of jokes, including parody Let's Plays.
  • One True Threesome: With the inclusion of the Legendary Ms. Chalice as a playable character in the upcoming "Delicious Last Course" DLC, many fans will ship both of the two protagonist brothers with her in art, making it a bit of a weird Love Triangle.
  • Portmanteau Couple Name:
    • DevilDice = The Devil/King Dice
    • DevilCup = The Devil/Cuphead
    • DiceCup = King Dice/Cuphead
    • DevilMug = The Devil/Mugman
    • DiceMug = King Dice/Mugman
    • CalaMug = Cala Maria/Mugman
    • CalaBerg = Cala Maria/Hilda Berg
    • CarnaBerg = Cagney Carnation/Hilda Berg
  • Ron the Death Eater: Very much downplayed, but due to the fact that his greed and carelessness kickstarted the game's main plot, Cuphead is frequently depicted as having some sort of mean streak, such as being a Deadpan Snarker or an occasional Big Brother Bully to Mugman.
  • Rooting for the Empire: Thanks in part to Evil Is Cool, there's no shortage of people who want to see the Devil and King Dice succeed in their scheme.
  • Scrappy Mechanic:
    • You can't change direction while both jumping and firing. In a game where you're firing your weapon most of the time, and you need every bit of mobility to dodge the hoards of hazards directed at you, this can be a real pain in the ass sometimes. As a result, many of the Run'n'Gun levels and the bosses with moving stages, most notably Rumor Honeybottoms, become even more difficult than they already are.
    • The lack of invincibility frames after the 1st Special Ability will get you hit at least once.
    • The game's use of RNG to determine things like when and where enemies will spawn, what attacks bosses will use, and where the platforms appear in Grim Matchstick and Rumor Honeybottoms' fights makes certain parts much more difficult and much less fun at times.
    • You can't use your EX specials once your Super Meter is full. This is annoying if your meter is full, so parrying or attacking more would be a waste, and using your Super Art would be overkill or you'd rather save it for later, but you'd still like to use an EX to speed up the current phase of the battle.
    • The game, which is Nintendo Hard as is, has a Simple (easy) mode, but you need to beat all the bosses on Regular mode to reach the endgame, making Simple nigh-pointless.
  • Some Anvils Need to Be Dropped: Gambling is bad, and gambling for more than you can afford to lose can be catastrophic. The game is not very subtle about its message, given how the casino is run by literally Satan, but it can be mostly forgiven as the cartoons it pays homage to were similarly Anvilicious and the message is still one that more people could use.
  • Stuck in Their Shadow: Poor Elder Kettle. Despite proving himself to be a Reasonable Authority Figure, he's usually ignored by the fandom, since he only appears at the very beginning and end. Some people even forgot that he was in the game at all.
  • Surprise Difficulty: How hard would you expect a game with a 1930s aesthetic and cute cartoon characters to be? When you know that it's a Parodius-esque Cute 'em Up Boss Game inspired by Run-and-Gun games like Contra and Metal Slug, it’s VERY HARD.
  • Suspiciously Similar Song:
    • A portion of the music for the Funfair Fever run-and-gun stage uncannily resembles the Athletic theme from Super Mario World. It's likely that said portion is actually based on the "Maple Leaf Rag" by Scott Joplin as with Mario, but the resembling portions of either song share the same chord progression. As usual with these similarities, SiIvaGunner pounced on it and made a rip about it.
    • "Inkwell Hell" begins with the rhythm from the James Bond theme, before the melody veers off in a different direction.
    • "Honeycomb Herald" sounds like a lawyer-friendly copy of "Caravan" by the Duke Ellington Orchestra.
    • "Shootin n' Lootin" and "Closing Credits" borrow part of their melodies from the Cab Calloway song "The Man from Harlem".
    • "One Hell of a Time" is kinda similar to the "Sigma Boss Battle" theme that is played in the first phase of Sigma's battle in Mega Man X1.
  • That One Attack:
    • Probably the earliest horrible attack you'll face is Ribby and Croaks' slots when they roll Tigers, which takes the form of several spinning platforms with spikes at their sides and bouncing balls at their tops coming at you at high speed. There are very, very few safe spots during the whole thing and really good reflexes will be necessary to make it through.
    • Among Baroness Von Bon-Bon's many minions, probably her deadliest is the innocuous little jellybean soldier that sprints out from the gate at random intervals from the second phase onward. It's so tiny and moves so quickly along the ground that you're almost guaranteed to overlook it and get hit by it the first time, and probably at least a few more times afterward because it's so hard to notice when all hell's already breaking loose around you.
    • Rumor Honeybottoms' triangle attack during the second stage of the fight. The triangle itself deals damage and Rumor likes to summon it right on top of you or above you, which becomes problematic when you need to move up due to the nature of the fight. Even if you can move out of the way, it still moves in your direction and fires three rounds of tiny triangles from its three tips, of which the first is fired almost immediately. Every attack sequence that involves these always has you deal with two of them summoned after each other as well. This attack is the #1 reason to bring the Parry Sugar to her fight, as it's one of the few truly reliable ways to shut it down (everything involved in the attack is pink).
    • Cala Maria:
      • Her Ghost Pirate summon. They move extremely fast, making them hard to avoid. If she uses it while her pufferfishes are active, dodging both attacks is even harder.
      • Her stare that turns you to stone. Better hope a projectile isn't heading towards you when you get hit by it.note 
    • Beppi the Clown:
      • The penguin clowns that shoot baseballs at you in the final phase. More specifically, the actual baseballs, due to their sniper-like accuracy and tendency to trap you in bad spots.
      • Many people are also irked by that goddamned rollercoaster train in Beppi's second and third phases. It's fast, enough to pretty much always catch you if you're on the right side of the screen (and it covers what would otherwise be a safe spot from Beppi in his third phase), and while it does have a tell, it's easy to miss since it's small and part of the background. It gets noticeably faster for the fourth phase, but it's not as bad then since now there are platforms that are safe from the train.
    • Fireball bubbles, tossed out by Grim Matchstick's final phase. Their patterns are troublesome enough, but they also force you to hold your fire, or else you'll accidentally pop them and release several more projectiles. As soon as they start getting spammed, either your damage flow suffers or you'll get caught in a fiery nightmare.
    • The barrel in Captain Brineybeard's battle. Like the jellybean soldiers, it's easy to forget about this attack because it hovers just outside your peripheral vision and you have to worry about the other attacks coming towards you. And unlike the jellybean soldiers, it stays the entire battle instead of one or two phases. In addition, it's indestructible, but it still attracts the Chaser's bullets, making that weapon practically useless in the fight.
    • Djimmi the Great can start his battle with one of three attacks he'll use until the phase is over, and one of these is an order of magnitude worse than the other two: The cats. Cat sarcophagi, to be specific, that split open and send out several more homing cat projectiles, while the sarcophagus halves remain harmful, resulting in a screen full of pain in a matter of seconds. People are known to keep restarting the fight until he pulls a different trick, as the flying swords and even the jewelry toss are much less likely to result in a terrible start.
    • Sally's Big Wave attack in her third phase, due to being impossible to avoid if you miss the parry star, bounce off of it too early, or don't equip the Smoke Bomb charm (which lets you dash through enemies without taking damage).
    • Dr. Kahl's gems of death, which bring true Bullet Hell into the game in a segment where electric barriers are already closing you in, not to mention they never stop coming until you win or die, are probably responsible for more deaths than any other attack in the game. "Got the perfect equation to hinder yer evasion" indeed. Luckily, they've been nerfed, with actual parriable pink projectiles being shot out along with the usual death-inducers, so the load is at least lightened.
    • King Dice's first intial attack may catch some players off guard, since he's the only boss who doesn't wait until the fight introduction is finished before attacking and his hand is likely to slap you down. The rest of them aren't quite as bad, but there's some minor Hitbox Dissonance with his marching cards due to their boxy shape and deceiving size, and thus parrying them properly can be quite erratic until you get used to it.
    • Most of the Devil's attacks are fairly easy to predict and dodge after a go-through or two... except for the fire spell. When his eyes light up and that trident starts spinning, only the Random Number God knows which of the three fireball patterns he'll be tormenting you with, and all of them are insanely fast and screen-crowding.
  • That One Boss:
    • 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 at random and are nearly impossible to notice against the rest of the chaos onscreen. And her final stage, 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's 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.
    • 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 fire bubbles mentioned under That One Attack. 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, on Expert, 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.
    • There's also Wally Warbles for the plane levels. This is the point where Bullet Hell really kicks in; his feather attack will force you to learn how to maneuver through a hail of projectiles with very little breathing room, keeping a steady hand as well as keeping the boss in your line of fire. Wally Jr. and his egg barricade 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 attack challenges you to keep track of three separate sources of erratic projectiles while returning fire. If you don't learn the lessons this fight teaches you, the later plane levels are all but impossible.
    • Rumor Honeybottoms forces you to continuously get away from death coming from a rising floor in addition to avoiding a 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 his patterns are predictable, so much is being thrown at you at once that it hardly matters. 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, everybody seems to dread Phear Lap due to all the dead trees in the foreground being a major source of Interface Screw that blocks the view of the player, which is absolutely horrible for a Shoot 'em Up sequence. 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.
  • That One Sidequest: Getting P-ranks on all six of the side-scrolling stages. The first few aren't too bad, but getting it on Perilous Piers is nigh-impossible without at least an extra heart. To wit: the last leg of that particular level leaves you stranded on a tiny space maybe five or six steps wide. Enemies will be attacking you from both front and behind. And you can't shoot a single one of them. Oh, and you have to remember to keep parrying the pink jewel, or say hello to Cuphead's Super Drowning Skills. Have fun!
  • They Wasted a Perfectly Good Plot: Battling against the Devil's debtors to earn your freedom could have made for an actual interesting story, but none of the debtors are ever developed beyond "boss for you to fight" and the plot remains an Excuse Plot throughout. Somewhat justified due to being based on old 30s cartoons that didn't really have much of a plot, but still disappointing.
  • Unexpected Character: The Legendary Chalice as the third playable character, Ms. Chalice, in The Delicious Last Course.
  • Viewer Gender Confusion: Being a giant flower, Cagney Carnation gets this sometimes.
  • Visual Effects of Awesome: The game succeeds in capturing the art style of 'toons from the mid-20th century without looking out of place in a game that runs at a silky smooth 60 FPS. Seriously, just watch gameplay footage at 720p60 or higher, or play it on Xbox One X and be amazed.
  • Wake-Up Call Boss: There's two of them! Namely:
    • For the Run N' Gun style levels there's Cagney Carnation, who forces you to start paying attention to attacks coming from multiple fronts from the very beginning, and his attacks are harder to dodge than the bosses before him. During his last phase, he plants his thorns on the ground, limiting your movement to the three floating platforms.
    • For the plane levels comes Hilda Berg who rolls over you like a steamroller with everything from flunkies, untelegraphed moves, and attacks that require tricky timing to dodge. If you go in expecting an aerial version of The Root Pack to warm you up for the plane battles, Hilda will skin you alive.
  • What Do You Mean, It's for Kids?:
    • With constant references to tobacco, alcohol, gambling, and rather disturbing imagery, as well as the Devil himself along with a few mentions of Hell, would you believe that this game is rated E by the ESRB? It's almost as if they're applying the Values Dissonance of the time period this game is paying homage to.
    • And while nobody is saying that kids can't enjoy difficult games, the cutesy cartoon look of the game belies a wickedly difficult Run-and-Gun game, which might catch both kids and parents off guard.
      • Furthermore, for the Switch version it's been specified that the difficulty has not been dumbed down, so that new players will get to experience the game as it was intended.
  • What Do You Mean, It Wasn't Made on Drugs?: Justified as the game is based on 1930s cartoons, which heavily relied on Toon Physics and gratuitous use of Surreal Humor. Thus, many of the boss fights in this game can get very weird, to say the least.
  • The Woobie:
    • Mugman, who, through no fault of his own (thanks, Cuphead), is forced to do the Devil's dirty work.
    • Ollie Bulb, the second of the Root Pack, who upon arrival seemingly looks for the recently defeated Sal Spudder and whose power happens to be Ocular Gushers. He's probably the only boss of the game who doesn't outright mock you when you lose to him. At least, you can leave him alone and let him depart in peace after the 1.2 update.
    • Grim Matchstick's game over quotes also seem to be more good-natured than those of the other bosses. Some of the faces and movements he makes look kind of goofy, theatrical, and even Adorkable, making it seem like he bears no real ill will towards Cuphead and Mugman. His stutter may also make him more sympathetic. There are also theories that he made his deal with the Devil because he was lonely, which would certainly land him in this category.
    • Sally Stageplay becomes one in the 1.2 update if you decide to stand on the two cherubs and make the chandelier crush her husband to death; she even cuts her first phase short to cry for him.

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