IceDevimon increasingly becoming the Butt Monkey throughout the one hour special. Everyone from the previousseasons must have written this episode.
It becomes even more Hilarious in Hindsight when you realize DaiPenmon, who sticks IceDevimon inside one of his popsicles and licks him, is the evolved form of Tomoki, who had his own disturbing encounter with such a Digimon.
In the dub, Jeremy shares a voice actor with Ken. They sound the same, but there is a stark personality contrast. As a result, transference can happen, causing returning fans to imagine Ken doing wild, crazy things.
In episode 12, Blastmon missing the team in his charging tackle...and he keeps right on going into a cliff.
Along with his reaction to Cyberdramon's attack in the same episode: "Are you giving me a hug? Are you trying to tell me... you love me?!?"
Then there was Akari geting the wits scared out of her in the Hot Spring.
Taiki and Zenjirou protecting their modesty with Starmon and the red Pickmon.
Akari and Zenjirou's love dance in episode 19.
Made even funnier by the way in which Taiki subtly sidesteps being roped into the dance himself, which results in both Akari and Zenjo commenting that this should be the point where his Chronic Hero Syndrome kicks in.
Zenjiro: These sort of moments are exactly the kind when...
Zenjiro/Akari: You shouldn't turn your back on us!
Also, Beezelebumon, one of the Pawnchessmon, Deputymon, Dorulumon, and even freaking Cutemon bail before the dance even starts, their expressions are priceless!
Dorulumon: It's utterly mortifying.
Meanwhile, Ballistamon, Knightmon, and the rest of the PawnChessmons are totally into it. Ballistamon's reaction to Lilamon demonstrating how the dance worked was pretty funny as well.
Episode 23. BalliBastemon. 'Nuff said.
How about Dorulumon digging a hole to hide and not tell a joke?
Episode 26 has this beautiful gem. Near the end of the episode, we see Blastmon reduced to a head. The rest of the generals made fun of him, but what's hilarious is this...
Blastmon: Tac-chan, I can't reach the candy!
Much of episode 27, including Cutemon strong-arming Dorulumon into using his drill tail as a beater through sheer cuteness!
Episode 31 has this nifty screenshot◊. Taiki's face just makes it more hilarious.
For context: Shoutmon had just evolved for the second time ever, after spending most of the episode doubted by Kiriha and Lilymon. At that particular moment he's busy tossing around Dorbickmon's entire dragon army.
MarineAngemon's Ocean Love is both awesome and funny at the same time, observe.
Nene: (to Dorulumon) I'm telling you to the teacher!
Kiriha: What teacher?
Greymon being possessed by Olegmon. Cracked this Troper up.
And the especially Bad Ass Cyberdramon being possessed by Olegmon adds more lulz. It's about time Blue Flare got involved in the slapstick.
Dorulumon's reaction to Cutemon getting brainwashed by Olegmon. The face totally sells it.
Dorulumon: Cutemon's broken!
Episode 44 has GreatestCutemon. Throw in a few random, not really battle-oriented Xros Heart Digimon, and you've got an armored Cutemon the size of a building who still cries like a baby when getting shot at. It's crowned by the Cutemon component that was his head flying off and the rest of the body running after it in panic.
The finale. Mervamon glomping Beelzebumon. That is all.
To make this even funnier a add popped up at this exact moment and said "congratulations you won"
In Episode 53, instead of the team having a great battle with Chu-Chumon, Taiki releases Bastemon, who in turn, eats Chu-Chumon