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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!
Hypnos is run by a small enclave of powerful people with top-secret knowledge... And one who doesn't know anything about digimon and plays golf while on a conference call with the others. Even better is the way in which a female representative explains things to him. Anybody who was a fan as a child can remember this conversation with their parents.
Female Member (dub): No, it's digiMON, not digiMEN, you dolt!
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 way Jeri yells "Why are we in the bushes?" when Kazu and Kantor drag her there is just priceless
When Takato is calling up the other tamers and trying to pump Jeri (who is running all over the place at this point, chasing Leomon) is just pure gold.
Jeri: (on the other side of the park) Yeah?
Takato: Are you sure he's your partner?
Takato: How come?
Jeri: Because it's destiny!
Takato: Okay, thanks! (to Henry on the phone) She says it's destiny
Jeri: You can't escape destiny, Mr. Leomon!
The owl from the Sinduramon episode, shouting about "The DAAAY-VUH has ARRIVED! OH YAAY-YUH! HAIL TO THE DAY-VUH, he who drinks from the light of man and exPANDS himself and looks like a right BIG chicKEN!". 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!
Takato (to Riley): Hey, I know you. You're that woman that comes by and buys day-old bagels.
Yamaki: Those bagels were day-old?
Episode 37: Takato is telling Rika about how he talked to their parents, and pretended to be her so as not to worry the latter's mom. Rika is genuinely grateful.... until she asks him if he did anything cutesy like put hearts in the message. Cue Takato getting an Oh, Crap look on his face, and a flashback that shows he did in-fact put hearts in his fake Rika message. Needless to say, Rika is not the least bit amused.
Rika then adds that he could've at least put smiley faces instead of hearts, so Takato quickly lies about doing that...she is even less amused.
Terriermon. The little guy gets some of the best lines in the show between his snarking, and lampshading events. And of course, there's his "Momentai" catchphrase. And then there's his reaction to other characters saying it:
The time has come for Takato and the tamers to go to the Digital World to rescue Callumon, and the kids have the dilemma of how to break the news to their parents. Do they lie? Do they dance around the issue? Do they just run off without saying a thing? If you're Takato you just walk straight in with Gullimon in tow as if it's perfectly normal and just like any other day. Admittedly the existence of real digimon is already out of the bag by this point, but still... His parents' reaction is epic.