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This is a "Wild Mass Guess" entry, where we pull out all the sanity stops on theorizing. The regular entry on this topic is elsewhere. Please see this programme note.
Cucumber Quest
The Nightmare Knight is being "evil" for show; the Oracle might be the true villain.
The Nightmare Knight, despite his appearance and demeanor, doesn't seem too bad. Sure, he's decimated a few places using the Disaster Masters, but he seems to care about the heroes. He let the gang through the Intermezzo Wall, he was likely the one who stopped the Noise Blaster, and he (accidentally) spends his free time helping Princess Parfait and listening to her problems. The Oracle, on the other hand, doesn't care. She forgets everyone's names, uses Chardonnay to clean toilets, and most of the "nice" things she's ever said were complete lies. She didn't even put effort in hiding the Disaster Stones. My guess is that the Oracle is using the Nightmare Knight to make her seem like a powerful and benevolent guide of sorts. The Knight causes mayhem for her; she hires heroes to capture him, and years later he's released once more, like clockwork. It keeps the bunny people grateful and willing to follow her. But things are different this time; the hero's a weakling, his sister won't sit still and be kidnapped, and even the Knight's slipping up by befriending those he's supposed to fight. Somehow, this will cause the whole system to fall apart, and the Oracle will NOT be happy with any of them.
  • To further this, the Disaster Masters are not in on this deal, and in fact the Nightmare Knight himself isn't aware of the Dream Oracle's interference and is just resigning himself to his reputation. Perhaps he had tried previously to do good, or he was the original guardian of Dreamside, but after so many years he's completely forgotten his original intentions and just goes along with it.

When the time comes Princess Parfait will refuse to sign the dream sword to seal away the Nightmare Knight
  • Princess Parfait seems to see some good inside the Nightmare Knight, and sincerely cares about him as a friend. She wouldn't want anything bad to happen to him. Plus she's likely to be the last princess they have to ask to sign the dream sword, and if she refused to sign it that would force the heroes to come up with some different resolution than sealing him away.

The Nightmare Knight will help (or allow) Parfait to escape the Caketown Castle.
A guess based on the interlude title picture. Parfait is shadowed in purple, making a "ssh" gesture, and surrounded by purple stars.

Parfait will fall for The Nightmare Knight, or vice versa.
Face it, he's much more interesting than Carrot. Parfait and The Nightmare Knight also seem to be two of the saner characters in the comic, and he's already helped her out once. And look at the wallpaper for the current interlude - pink hearts and purple stars!

Lettuce will help Parfait escape Caketown Castle
Lettuce is known to have a crush on Tomato. She'll help Parfait leave so she's out of the way thinking if Parfait is gone she'll be able to get Tomato to give her the kind of attention he gives Parfait.

The Nightmare Knight created the barrier.
Purple stars are his thing, after all. Noisemaster knows this, which is why he just gave up. Which also explains the "So, it's like that" callback.
  • It's been confirmed on Gigi's twitter that anything purple and sparkly is an effect of the Nightmare Knight's magic which would include the barrier. Him saving Trebleopolis, and Dream Oracle lying and taking the credit for it has been lampshaded enough in the comic and talked about on twitter that it should be considered canon by this point.

Cosmo created the Noiseblaster, AND the barrier that stops it
Noisemaster's smart, but he's not been shown to be good enough with machines to make the noiseblaster on his own. Unless a character who hasn't been introduced yet did it, Cosmo is the only tech-smart character we've seen that could help him make the Noiseblaster. But Cosmo's also a really sneaky kid. It's likely they're Playing Both Sides and sold the tech for the barrier to the people of Trebleopolis to make a profit off of both Noisemaster and the innocent citizens he was going to destroy. Cosmo probably got the idea to exploit the whole legendary hero thing for profit when they learned about it from Almond in Caketown.
  • The barrier half of this has been Jossed. The Nightmare Knight did that.
  • However, the Noiseblaster is looking increasingly likely. Cosmo seems to be working for "Glitch—-," the character first shown here. Since "Glitch" seems to be behind the Noiseblaster to some degree, it's very likely that Cosmo is as well. Plus, there was a Word of God somewhere that Noisemaster had gotten help building the Noiseblaster.

Cosmo is a Disaster Master in disguise.
Specifically, they'll be the one encountered in the Space Kingdom, due to the star pattern on their coat. It's entirely possible that they used their mad scientist skills to create some sort of cloaking device and is pretending to be a citizen. Furthermore, they appear immediately after the scene in which the Nightmare Knight is resurrected (and seven beams of light shoot from the castle, most likely releasing the Disaster Masters). Presumably, they're the most capable of the Knight's servants, and is out to foil the heroes through use of Obfuscating Stupidity - their inventions have always 'malfunctioned' in ways that could have killed them if they weren't lucky, and always while they were attempting to travel to another kingdom.
  • All those question marks on their stat sheet are rather suspicious...
  • Furthermore, it seems likely that the Space Kingdom's Disaster Master is the one represented by the Disaster Stone with a power symbol on it. That would be a pretty suitable symbol for a Disaster Master who works with technology.

The Nightmare Knight and the Oracle are siblings
Just a hunch.

“Queen” Cordelia is the Space Kingdom princess.
We know there's a Space Kingdom. It may not be on the map – at least, not the one in Saturday's tower – but where else do spaceships come from? Queen Cymbal even mentioned it once. Cordelia constantly hints that she's from Space Kingdom. She rants about what she'll do to this planet, how she'll take over this planet, how this planet shall bow down to her, etc. etc. She has those “weird ears” similar to COMMANDER CABOODLE, CHAMPION OF JUSTICE! (Who, interestingly enough, seems to know about her evil scheming. The main characters wouldn't have found out if not for Lord Cabbage and the Dream Oracle...) Her color scheme also fits the disaster stone that bears the power symbol. Whether she's a princess or not is just a guess, but this troper thinks it would add to her character a great deal. Plus, when Nightmare Knight inevitably betrays her, she and Peridot can (begrudgingly) join the heroes' side.
  • No, her ears aren't right. The first book has a page talking about how you can tell where each person is from based on their ears. Space Kingdom bunnies have wide ears with a symbol inside, like Cosmo. The Space Kingdom (on the moon) is still considered part of Dreamside, the whole world. The same ear page also says "If they've got cat ears or something, like Cordelia, they probably aren't from Dreamside."

Saturday is the Flower Kingdom princess.
Her ears have sprouts on them, indicating she's from the Flower Kingdom. The first book says that the Flower Kingdom is known to some as "a land of dangerous ruins for intrepid adventurers to explore!" Such a place might inspire an adventurous princess. And besides, what kind of thief has a butler? One that's a runaway princess with a royal servant. Also, Cucumber's reaction would be funny, which is a good enough reason for this series.

Noisemaster and Legato are Co-Dragons, conspiring to overthrow the Nightmare Knight.
It's been theorized that Legato is working for or in conjunction with Noisemaster for several reasons: two of the tentative Disaster Stone designs seem to match them perfectly; what looks like Legato's speech bubble color shows up in Noisemaster's broadcast from Rhythm Ridge; Noisemaster talks about scheming with an unseen partner-in-crime; and legato, or "tied together", refers to smooth transitions between notes in music. It's possible that these two could actually have ambitions of their own. Consider that...
  • The Nightmare Knight and the Disaster Masters have been summoned and defeated 100 times, and a common fan interpretation of the NK himself (which recently gained support from the page where he blasts open a wall obstructing Cucumber's group) is that he's secretly helping the heroes because he wants the cycle to end. Noisemaster might have a similar motive, in that he blames the NK for their failures and wants to take matters into his own hands.
    • Noisemaster was briefly shown to act darker and more cunning when the NK wasn't around. His Totally Radical schtick is to keep suspicion off of him. When he told the NK that his scheme would "put ya in the hospital", it wasn't just a figure of speech.
Most likely, Noisemaster and Legato plan to turn the Noiseblaster on the Nightmare Knight once it's fully-charged. A laser that can take out a whole kingdom could do some serious damage to the final boss. Finally, the Nightmare Knight might actually be expecting this ( especially if it's happened before), which is why he wants Cucumber and friends to reach Noisemaster and defeat him.

Legato and Noisemaster being Co-Dragons has been Jossed, although still waiting to see whether or not Noisemaster is planning a betrayal.

Also, the Noiseblaster can be powered up with the screams of the princesses (or just ordinary people, too).
Think the Scream Extractor from Monsters, Inc., and we know Princess Piano is pretty much the loudest character in the comic so far. It's also why Legato is so gleeful over finding Nautilus, because it means they can power it up even faster now. (Second part Jossed for now, but might still come back.)
  • First part is confirmed, however.

Noisemaster and Legato are somehow related to the king on the other side of Intermezzo Wall.
Lute referred to Legato as a sorcerer and said that he was at least a century old (we don't know how long the wall has been up, but the Melody Kingdom does have rumors about it being full of ghosts on the other side), so he could've been the king's magician. If Noisemaster didn't have anything to do with the aforementioned rumors by just wreaking havoc over there, he might actually be the other king; he made some sort of deal for power with the Nightmare Knight to get revenge on the rest of the Melody Kingdom.
  • Furthermore, the Nightmare Knight specifically says he can't believe Noisemaster "is still talking like this", implying at some point he did an overhaul of his style.

Cucumber will break the cycle of the Legendary Hero once and for all.
Most of the other characters have been stealing the spotlight, but eventually his character arc will end in a lesson about how there are multiple ways to be a hero (or that nobody HAS to follow the genre 'rules') when his extensive magical studies allow him to stop the Nightmare Knight and Disaster Masters from being brought back every 5,000 years. The Nightmare Knight might even be redeemed.

Legato is some kind of ghost.
Not a whole lot to say, but he does have strange powers, still looks young despite being "an ancient evil", and he might have some kind of unfinished business or mental block keeping him from passing on to the other side.
  • Jossed. While interrupted, one of the ghost instruments said the Legato in the comic is different from the one from the legends.
    • Although it's been revealed that he put at least a fragment of his powers and personality into Panpipe's contact lens.

Almond and Peridot will get together in the end
They both seem have crushes on each other, due to how often they end up helping each other out. Either that, or Peridot's love in unrequited.

Legato's contact lens will reappear later on.

X will officially ally with the Cuquistadors sometime before the end.
  • Commander Caboodle
  • Saturday
  • Peridot
  • Count Legato (Either Panpipe, or a third one)
  • Princess Piano
  • Bacon (Just covering all the bases here)

The "Borrowed wand" is actually a legendary artifact
...Thus explaining why it can meld with the Disaster Stones.

Noisemaster's Noiseblaster was blocked by either the Space Kingdom Disaster Master or The Nightmare Knight.
If the former, it's so that Cucumber and Co would have a chance at still beating Noisemaster so he can fight them himself. If it's the later, it's because it was a plan that not even The Nightmare Knight would have approved of or he has a code against wholesale slaughter of innocents. When Noisemaster had a plan that was "So ill, it'll put you in a hospital", he might have been literal, a plan that Nightmare Knight wouldn't be able to stomach.

The Noiseblaster was blocked thanks to assistance from the Space Kingdom
When they said that Princess Piano's screams reached even the Space kingdom, this was not Hyperbole. Somehow, they were able to figure out that this time wasn't a case of Crying Wolf, and they sent someone to help.

Cucumber will turn against the Dream Oracle soon.
The ending of chapter 2 shows that his objections to her behavior are getting much stronger and worse, and the ending picture shows him cast in a darker light. The question is whether this would actually qualify as a Face-Heel Turn or not...

Cucumber quest has started a Deconstruction arc, but will eventually wrap around to a Reconstruction again.

The one who will ultimately end the cycle...
... is none other than Nautillus.

Face it- Cucumber doesn't want to be the legendary hero, and Almond is fully willing, but it's Nautillus that has been given a bit of specific focus over the past few chapters- she did the most during chapter 1, and it's specifically her that is able to deal with Noisemaster last. The story could likely set itself up or subvert both the expectations that wither Cuco or Almond will break the pattern on their adventure by having her find a way in their stead.

The Disaster Master of the Flower Kingdom will be named Weed Master.
So far, all of the revealed Disaster Master has this inverse relationship to the kingdoms they are sent to. A large Splash versus a gentle Ripple. Noise and Mute(ness) versus Music. What better way to oppose gentle flowers than with nasty weeds that choke the life out of other plants? On that note, if the Space Kingdom is high technology, their Disaster Master will be Glitch Master. Perhaps he had an early cameo here?

Queen Cordelia and the Nightmare Knight will go their separate ways soon, one way or another.
Either Cordelia will switch to using alien technology and turn out to be Eviler than Thou, or the Nightmare Knight will take over fully after getting tired of Cordelia's attitude.

Peridot is helping Cordelia not just For the Evulz
My guess is that Peridot didn't exactly have a great past. She's seems to be a sort-of perfectionist magician who freaks out at failing at anything, and acts high and mighty to cope with the stress, but she doesn't really have any friends because of her attitude. However, when Cordelia came along, she was the first person to actually care about Peridot, and even makes her feel appreciated and comforted despite any mistakes she makes. To Peridot, she wants to make it up to Cordelia by being her number one minion that Cordelia can rely on.

Caboodle is related to Cordelia in some way and wants to bring her back to their home planet.
We already know the the "Queen" is a cat in a world full of rabbits, perhaps she had her own spaceship and it crash landed and without any other idea on how to get home she decided to make a living on Dreamside by trying to dominate this strange bunny land. Caboodle is off to try and find Cordelia before she causes much more madness than she already has and bring her back where she truly belongs but it has been a bit of trouble on the way. As for their relation I would either say a sibling, cousin, or her crazy husband who is way into being a space warrior.

The legendary hero isn't just meant to defeat the Nightmare Knight. He's also meant to take his place.
Taking into account the Knightmare Knight's jaded attitude, how he's doing everything like he's going through the motions to the point of almost looking tired of it, like he's acting out a role in a play he hates. Consider how he straight up saved the Melody Kingdom when it came into real danger, or even how he actively helped Cucumber past the magical locked door. Consider their surprisingly similar personalities, and how Cucumber showed instant proficiency in using the magic of the disaster stones. It's not impossible the Knightmare Knight was the previous hero, having defeated his predecessor and forced into taking the mantle, just as his predecessor had. He may be jaded because he knows Cucumber will succeed, only to be become the next Knightmare Knight and continue the cycle.

The Space Kingdom's Disaster Master will be named Glitch Master
This is in keeping with the noted 'inversion' of the names of the Masters in regards to the Kingdoms they terrorize. It would also fit, as for a Kingdom that is almost certainly highly dependent on technology, some sort of rogue, malevolent AI or Anti-Tech being would be absolutely terrifying.
  • On top of that, Cosmo - all but explicitly said to be Space Kingdom - comes close to saying it here right as... something teleports them away. Complete with dead pixels and artifacting!

Glitchmaster is The Man Behind the Man

Cosmo is both Glitchmaster AND the Space Kingdom Princess.
How else would a 'glitch' exist but as a malfunction in something else? In this case, inside the system of an otherwise only slightly eccentric, techno-savvy princess...who seems to have constant problems with their otherwise fine inventions constantly 'glitching'

(Cosmo's gender is never specified)

"Glitchmaster" is the original Nightmare Knight, and created the current one in his image.
The hologram form of Nightmare Knight is actually his true form, and Nightmare Knight seems too nice to be the real main villain. Since "Glitchmaster" is so far the most ruthless character shown, working on the Noise Blaster, his interaction with the heroes in the most recent pages, possibly having an Evil Plan to "annihilate" Dreamside, it's possible that HE was the Nightmare Knight that "brought destruction" all those years ago, as that seems more in character with him as opposed to the actual Nightmare Knight. Maybe Nightmare Knight is another Disaster Master, one who's designed to look like the main villain as a decoy.

Also the Moon seems like a much more appropriate place for a final battle than some castle in the middle of a candy town.

Glitch——- isn't actually a Disaster Master
It's possible- why else would the static cut off what WOULD have been the "Master" in his name? Relating to the above, maybe it's "Glitch Knight"?

We know she's definitely from the Flower Kingdom because of her ears. Maybe when the royal family was wiped out from the last attack from the Nightmare Knight, someone snuck a survivor out and that family has been living as thieves ever since. Might explain why a thief would have a butler, in any case.

Caboodle will join the party
His ship was blown up, all he (might) have is the clothes on his back, he considered Cucumber and co to be FELLOW ALLIES OF JUSTICE, and he's on the title page of Chapter 3. Need I say more?
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