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  • Kross attempts to jump onto Amber while she's in her dragon form, but due to a bad roll, he ends up getting thrown off of her.
  • The running gag of Oin threatening to grab Kross and Jalerom by their ears every time they do something stupid.
  • Kross having either terrible luck or amazing luck leads to several funny moments.
  • The exchange between Ivan and the skull.
  • Kross attempts another jump, this time across a chasm. Or so he thought until he hit an invisible wall and slid down to the ground that had been covered by the illusion of a chasm.
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  • Jeminya blurting out that she wants one of the councillors to "Ride her into the sunset." during a meeting, thanks to a truth spell.
  • The team are down in a lair, seeking a mysterious something that Jalerom has heard chewing, all on edge. Then Eliyora burps. The entire group loses it.
    Voice: "I-I thought that was the monster we were attacking!"
    Finn: "Someone do a burp check."
    Eliyora: "Shut up!"
  • Amber's defeat of the 'Smooth Criminal', mainly by pulling a Gohan and landing on top of it.
  • Another moment from Amber during the fight is her using her firebreath during the battle. That itself wouldn't be too funny, except that Jeminya is standing in the blast zone! Amber's Oh, Crap! expression is priceless, and one imagines that the Death Glare Jeminya gives her whilst on fire would be something akin to this.
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  • Jalerom's Mathematician's Answer when they bring back the corpse of the glimmercloak
    Councillor: "What is that thing!?"
  • Ivan meets two other cheerful and optimistic bards in a tavern in Sabaton. The reaction is about what you'd expect.
    "Oh dear God there's three of them."
  • The multiple jokes about Amber's appetite while they're in Sabaton.
  • The fact that Faethurin's hometown name of "Lefethyr" sounds like a certain bit of gibberish from Abridged!Kirito
  • Speaking of Faerthurin, the running gag in episode 18, with everyone mentioning Fae creatures and Fae thinking they’re talking about her. She eventually decides to change her nickname to Rin to avoid confusion.
  • The labyrinth was a terrifying experience, what with the balor chasing them and even having already killed Jeminya. But then, this happens:
    Josh: Roll Initiative, everyone.
    Voice of Reason: You've got to be f — GAH!
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  • The rather solemn tone and moment of Kross and Oin's conversation post-nightmare is broken by Jeminya suddenly yelling at them to go to sleep.
  • When The Warden shows up in Ivan’s nightmare.
    Eliyora: ”You’re Too CHEERFUL!!”
  • Fae literally begging to read a book.
  • Rose turning Aymer into a puppy is as hilarious as it is cathartic.
  • In a Call-Back to the “Ride Me into the sunset” line above, there’s this exchange when the party realises that The people they’ve been meeting are all Gods.
    Rose: ”And Jeminya? No offense, but I think that Elf councillor might have been a bit out of your league."
    Jeminya: ”What do you me- ...Oh Heavens, I fantasised about a God.
  • Kross utterly failing at romantic compliments.
    Kross: ”I got you this (garnet necklace), it reminded me of your eyes.”
    Jeminya: My eyes are blue, Kross.
    Kross: ...Oh.
  • This Line:
    Eliyora: ”Okay! Okay! No! Stop! You know that phrase “Tempting Fate”? Well Fate is sitting RIGHT THERE in the Dungeon Master chair!”
  • Doc lampshading his Team Dad status.
    ”Somebody call for Papa Wolf?”
  • The very first line in Episode 35.
    ”SCREW YOU, JOSH!!”
  • Oin’s extreme reluctance to help Kross when the latter is being thrown around by the Kraken.
  • This line from Jalerom when giving exposition on the Fire Elves:
    ”(Their Goddess) is a Goddess of fire, love and passion. So uh… (Walks up to Kross and places a hand on his shoulder) Have fun with that.”
  • Oin after Amber kicks the merciful crap out of Sazzan:
  • Jaelrom in the Trial of Guile. Just the entire Trial of Guile. But the funniest moment would have to be the following:
    Jaelrom: "Uh, I'm over there!"
    Troll: [turns around] "Huh?"
    [Jaelrom jumps on its back and kills it with his sword instantly]
    Guard: "[chuckling, whispers] That should not have worked."
  • Arguably even better, is him convincing the final troll to drink poisoned water. behold the power of lying!
  • The party lampshading the fact that they’re constantly in the dark about everything going on.
  • Simula, and Josh’s, growing frustration as the party takes an incredibly long time to realize that Ivan can just Shadow Walk out of the plane of Shadows.
  • The group learning that Amber can breathe underwater and that they were panicking in episode 35 over nothing.
    Lightning Bliss: ”SON OF A BASKET EATING BULLDOG!!”
  • Reyin loves handing out cookies when he gets the chance.
  • When the group encounters the Cheshire Cat outside Gatless Town, they start to chase him down....Complete with Yakity Sax playing the entire time.
  • In the third layer of the Nine Hells, the party finds a young tiefling girl who gives her name as Mori. They very quickly figure out who she is, however, and Jalerom, Amber, and Faerthurin all walk a way from the situation briefly to curse their heads off in varying languages.
  • While their adventures through the Nine Hells have very little humor to them, it's when they get to the fifth layer that they meet up with Saint Suviel, a man who's constantly shouting and has no idea what the phrase "be quiet" means and loves to get into fights. There are a lot of awkward silences while the party tries to figure out what this guy's deal is.
  • While on the sixth layer of hell, the party has had enough of Raavas's crap, so Oin, after giving a brief speech about what Raavas had inadvertently taught him, uses a spell to freeze time and then put Raavas to sleep, before having Faerthurin send him to an extra planar mansion.
    • True, it was to prevent Amber from just ripping Ravvas's head off, but the fact that this was done by OIN, of all people, is kind of what makes it funny.
  • When Oin visits Ravvas in the dreamscape following the party's victory over Baalzebul, the first thing Ravvas says is "Who died?" It's in such a casual tone that one can't help but chuckle at it.
  • Not long after entering Cania, the group encounters Mephistopheles, who greets them by throwing a snowball at Amber's face.
  • The rest of the group tries to follow Amber down into a crevasse in Cania, only for the edge of the ravine to fall off and land on Amber's tail. While everyone laughs at Amber's suffering, Amber compares it to having a large rock land on a human's big toe.
  • While going through the tunnels under Cania, Jalerom is in the lead searching for traps. Raavas gets a little overzealous and triggers a trap that fires a laser at his face.
  • This:
    Josh: What's this, Amber and Raavas being CORDIAL with each other?
  • Disarming the traps in Lolth's lair...WITH PLAYING CARDS!
  • After Fae identifies the magic that killed another poor sap in the maze, we get this:
    Faerthurin: This magical lesson has been brought to you by Faerthurin. Now you know.
    Raavas: And knowing is half the battle.
    Everyone: G. I. JOE!
  • In the middle of the battle with Lolth's consorts, Josh takes the time to point out that she's currently making out with one of her consorts. Everyone reacts just as you'd expect. Aramau sums it up perfectly in the Roll 20 chat:
    Aramau: JOSHUA
    JUST NO
    NEVER SAY THAT WORD AGAIN
  • When Jalerom pops the question to Faerthruin, everyone goes nuts and some have to mute their mics. Doesn't stop Josh from commenting in the Roll 20 chat:
    Josh: "My pancreas is gone. As are my teeth. My liver is dead. I am not long for this world."
  • After Jalerom and Faerthurin get engaged, Amber starts hugging and swinging Ivan around like a teddy bear. After Jalerom and Faertherum exit their room, Amber practically squeezes them breathless.
  • Upon Jalerom checking up on Oin before breakfast, Oin promptly leaves. Consequently, the construct of Rein mimics and disses him.
    Rein Construction: "I'm over there."
    Rein Construct: "Doesn't give it the excuse of being stupid."
  • When Simula projects herself into the extraplanar mansion while the group is having breakfast, the conversation becomes somewhat of a jabbing fight between her and her daughter.
    Hana: "I got it from my mother."
  • Sure, the first episode of Season Four is incredibly somber, but the mood keeps getting ruined by random burps and phone chimes.
  • The Cheshire Cat tries to speak with Oin, but pops up into the room Fae and Jalerom are staying in. He denies he didn’t do it on purpose, but no one believes it.
  • At one point, Faerthurin calls Rime a "harlot", though she later admits she only heard the word and doesn't know the true meaning. On the way to Gatless Town, Rime tells her the true meaning, and Fae is so mortified that she tries to cover herself up with Jalerom's cloak.
  • Faerthurin winds up changing her appearance to better represent Queen Jeminya. Even though he is definitely a respectful gentleman, Jalerom is not only dumbstruck by her new look, but winds up stumbling over his words, turning bright red, and making a poor excuse to escape the situation. Someone's turned on by formal wear...
  • In a dark sort of way, it's kind of humorous to see Oin's bad luck backfire on him during the fight with Ravvas and his drow assassins.
  • Speaking of dark humor, Finn engages in some after Ivan dies and the group is teleported to safety.
    Faerthurin: Did they bring everyone? Did they get Ivan?
    Finn: What’s left of me, anyway.
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