In Digimon TamersBridge Bunnies Riley (Reika) and Tally (Megumi) are doing their 'tracking Digimon bit' only to realize that the signal is coming from underneath their seats. They look down to find Calumon running around the control room. The clincher is when Tally completely loses her composure...and starts gushing over the thing.
Calumon's dialogue doesn't help.
Calumon: Calumon, zoom zoom, here a zoom, there a zoom! Calumon, zoom zoom, NO UNDERWEAR, ZOOM!
When Henry and Takato are trying to find a home for Calumon, Takato suggests Henry's place. After Henry brings up "Terriermon Torture", Takato goes into an Imagine Spot about what would happen. When he comes out, he promptly declares "Mom was right; my imagination is a curse." What makes this even funnier is the completely baffled look on Henry's face, an expression he had never sported before that moment and never sports again.
The episode "Not as seen on TV"(dub), episode 9, features Takato's attempts to De Digivolve Growlmon; he tries everything, from swiping a card backwards, exercise, praying, and just plain hiding him until he reverts. Did I mention that Takato and Growlmon (a big dinosaur/firebreathing dragon) try most of this together?
In the same episode, the random lady and her husband's toupée.
A little later, the same lady and her friend pass by Takato, Henry, and Terriermon.
Lady: Oh look, little boys playing with dolls. How cute!
Also, the Good Troi Episode "Juri's Partner? My Leomon-sama!" in which Juri wandered around the city being pursued by Culumon, chasing after the aforementioned Leomon, declaring (in the dub, at the very least) that it was their destiny to be Tamer and Partner, making googly eyes at Leomon and other such nonsense. Best moments: when confronted by said googly eyes, Leomon's reaction—flinching away with the words "Ahh, don't look at me like that!"; also, watching The Stoic, Bad Ass, Mega Nekoactually running around through the park to escape a little girl, and hiding behind a tree!
The reaction of the Power Trio is also great. "Okay..." "Tamers aren't supposed to do that!"
A sad episode with many funny moments; One of them is when Leomon and Takato meet:
Original - Leomon: Listen ...
Takato: *quick monotone* I am listening.
Dub - Leomon: Wait a second ...
Takato: *energetic* Sir Yes Sir!
Meanwhile, Guilmon catches Calumon/Culumon. Then, To defend him, he throws (without looking) Calumon/Culumon somewhere behind him!
Early on in the episode, Jeri is talking to Kazu and Kenta about Digimon. She says "I'm not into Digimon. I don't even collect the cards." Cue an enormous stack of cards falling from her person, which she hastily tries to pick up, looking quite embarrassed.
The owl from the Sinduramon episode, shouting about "THE DEVA! The deeeeeeva who drinks from the light of man and will become a ripe big chi-cken!". Henry's memories really emphasize the first two words.
Takato and Henry's deadpan reactions to it make it even funnier. After all the stuff they've been through recently, they're seriously not at all surprised to be speaking to a talking, glowing eyed owl!
When the Tamers first encounter the D-Reaper's agents. They decide to run away, but Guilmon was having a staring contest with them. He was winning too. It's less funny in the original, though, where there's no dialogue between the time when everyone else runs off and Takato pulls Guilmon after them.
In the Japanese version of Episode 37, Xiaochun feels Lopmon in pain, climbs up a pillar, and her Digivice somehow takes her away to Zhuqiaomon's palace. Throughout all this, Guardromon is watching her—and says absolutely nothing. It makes the following exchange hilarious:
Hirokazu: I told you to keep a close watch on her!