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For all that the story is billed as a much darker one than we've been told, this rewrite still has brilliant moments of hilarity.

Chapter 1: Courage Rekindled

  • TK's first meeting with Yolei and Cody involves the former bowling him over. He is then introduced to Yolei's smell
  • Cody helps Yolei with her homework. Please note that Cody is still in primary school while Yolei is in junior high.
  • Davis attempts to physically intimidate TK. Given that the later has faced down literal demons, it goes as well as you could expect. Especially once Tai shows up and greets his old friend.
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  • How does Davis get his D3? When it pops out of the computer and beams him in the face.
  • Everything involving Davis freaking out over the Digital World while Tai, TK and Kari take it in stride.
  • Gatomon's first impression of Davis: Whack job.

Chapter 2: Love Takes Flight and Knowledge Digs Deep

  • Our introduction to the Running Gag of Davis and Yolei getting into a wrestling match and falling into the school pond. Cody being able to time it precisely just ups the hilarity.
  • The first meeting between Davis and Ken.
    Davis: Who the hell are you?
    Ken: Your worst nightmare come to life.
    Davis: Bullshit! You ain't a ten-foot tall hydra with my sister's face for all yer heads.
    Ken: I concede; I'm not THAT nightmare.
  • Sora and Kari agree that not much has changed about the Digital World. They're still running for their lives and screaming while digimon alternately try to blow them up or eat them.
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Chapter 3: Light and Hope Return

  • Upamon learns that when it comes to food, what goes in must come out.
  • Yolei encounters a hologram of the Digimon Emperor. Cue the loud scream of "GHOST!"

Chapter 4: The Spires

  • Davis reveals that he is an expert in Malaproper.
  • Matt's jazz band nickname: Squeals. Too bad it's never brought up again.
  • Davis asks Cody to back him up when suggesting the Tony Stark method of planning an attack. Cody asks him if he's ever agreed with Davis.
  • Davis three step-plan for dealing with the Digimon emperor, we really shouldn't be surprised.
    • 1. Free the older kids digimon.
    • 2. Uproot the spires.
    • 3. Kick the Emperor out of town.

Chapter 5: Flora and Frost

  • The prune juice habit of Chikara Iori is alive and well.
  • Mimi's Alpha Bitch attitude is so annoying to Davis and Yolei that they call a temporary truce. This culminates in MIMI getting tossed into the school pond.
    • A subsection of that is where they basically kidnap Mimi away from her fellow cheerleaders.
  • Gomamon's Marching Fishes takes down Ken. For added hilarity, a similar occurrence would happen several years down the road in Tri.
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Chapter 6: Metal City

  • After Kari is stranded and Davis and TK race in to rescue her, Yolei and Cody decide to go inform the others. Unfortunately their digimon lead the way, resulting in a loud scream and a thump.
  • How are Kari and Gatomon found by Gardromon? Kari sneezes.
  • Yolei needs to grab her Digivice from Izzy so that she can help rescue Kari. Instead of entering calmly and explaining the situation, she blows through like a whirlwind, snags the device and leaves Izzy with the smell of rotten strawberries
  • After Jun calls Matt's place to arrange their date, Hiroaki comments that he was "startin' to worry".

Chapter 7: The Emperor Unmasked

  • Cody buys food for the soccer game agrees to let Upamon have half. Upamon then claims that his half was on the bottom after eating it all.
  • Sora shows up at the game to get some strategy ideas. After the boy's team gets thoroughly beaten, Tai asks if she's learned anything.
    Sora: Yeah, don't play Ken Ichijouji's team.

Chapter 8: When Rings Go Wrong

  • Even Yolei can't keep up with Izzy when he goes "deep geek".

Chapter 9: Downward Spiral

  • Davis complains about having to stay late and clean the blackboards, remarking that his teacher doesn't recognize the value of a quality paper airplane. Kari responds that it might have some to do with being hit by said paper airplane.
  • Davis mocking Ken's name by referencing South Park.

Chapter 10: The Storm of Friendship

  • After help Tai haul a passed-out Davis home, Matt is roped into yet another date with Jun.

Chapter 11: Purely Justice

  • Why don't TK and Patamon show up. They were busy trying to keep Jun away from Matt during his practice the previous night.
  • After Davis makes a crack about her weight, Yolei yanks Poromon out from under her shirt and smacks Davis with him.
  • How does Sora give the others time to escape from Starmon: she breaks a barstool over his head.
  • Mimi's description of her hoped-for funeral includes a pink dress and hordes of fanboys.
  • Deputymon's cheating in his duel against Starmon leads to the girls wondering which digimon is wearing the Dark Ring.

Chapter 13: Deep Dilemma

  • When they're trapped on the oil rig, Davis's method of entertainment is to repeatedly bang his head against a metal railing. You get the feeling this isn't his first time dealing with oxygen deprivation.
    • There's also his fantasized future which includes designing an airplane, being a championship soccer player, and "to experience the joys of manhood with Kari".

Chapter 14: Odaiba Memorial

  • Any of the scenes involving the employees at Fuji Television Station.
  • Cody comments that Hawaiian pizza shouldn't exist.
  • When Izzy asks Davis to try opening the Digital Gate on the Yagami's computer, he protests that it might blow-up. Cody's deadpan respone:
    Then we'll get a mop and notify your next of kin.

Chapter 15: Phail

  • This conversation:
    Davis:Just spin 'er a tale then! Tell 'er you won the Publicist's Jeering House Award an' you can miss school as long as you want! Or, uh... Oh, I know! You've been summoned to a planet with only hot alien women who want to breed a new race! Oh baby...
    Kari: Your parents would believe that?
    Davis: Nahh, they don't believe ANYTHING I say, anyway. It's no fair! I ought to be presumed incontinent.
    Cody: I'm sure you should. You really have to study your vocabulary better.

Chapter 16: Born of the Dark Pool

  • According to Tentamon, Joe and Gomamon got guard duty a lot during the first adventure.

Chapter 18: The Pitiful End of Royalty

  • Yolei comes up with a hilariously bad story to try to explain their various injuries. The hilarious part is that Kari is blamed for TK and Cody being beaten up.
    • Tai then bails them out by throwing Matt to the wolves. Or the she-wolf as it were.

Chapter 19: Brave New World

  • In a future interlude, TK bemoans having gone to bed. Kari gives him a look. Please keep in mind that they are married and have at least two children. Yeah, looks like he'll be on the coach for a while.
  • All the new Digidestined bring Davis get-well presents after he wakes up from his coma. Kari brings oranges, TK bring ginger ale, Yolei bring him an airplane magazine. And Cody brings him the homework he missed.
  • Jun discovers Demiveemon and begins subjecting him to the Running Gag of Marshmallow Hell.

Chapter 20: Digivolution for Dummies

  • Demiveemon asking Yolei if her lack of breasts means she's a boy. Even Kari giggles at this.

Chapter 22: Disbelief Before Dishonor

  • Yolei remarks that Davis babysitting the Punimon is a good thing as it would allow him to show-off his parenting skills to Kari. He reacts like any thirteen-year-old boy.
    • This leads to him being trampled by the Punimon a number of times.

Chapter 23: Needling Troubles

  • In one bit that requires a bit of meta, Davis is trying to get the other Digidestined onboard with giving Ken a chance. After Kari says maybe and Cody and Yolei give definitive "No"s, Davis concludes the only one left to ask is TK, but brushes the idea off because of their "rivalry". However in the original anime, TK was willing to give Ken some leeway and is the same way here.
  • Izzy's hilarious Double Take after passing Mimi in the hallway.

Chapter 24: Inheritance

  • Sora wearing a medical mask while taking care of the flowers. Her barely distinguishable dialogue sells it.

Chapter 25: Quicksand

  • Yolei freaking out over the zombie!Mekanorimon is rather amusing.
  • Izzy calling everyone at three in the morning to let them know he found Gennai.

Chapter 26: Reunion

  • The Digidestined (and their parents) were minorly irked by Izzy's late-night calling spree.
  • Cody is up for early morning Kendo practice and sees Yolei heading to her meeting with Mimi. When asked what she's doing, she tells him she's going for a walk. When TK heads to his own meeting with the older gang, he gives the same excuse. What's Cody's explanation for what he and Upamon are going to do:
    We're going for a walk.
  • Cody goes over to Davis's to recruit him into finding out what TK is up to, he does so by insinuating that TK and Kari are going on a date. It takes Davis all of thirty seconds to get dressed and come charging out. After rescuing Demiveemon from a sleeping Jun, he concludes that laziness is in the Motomiya gene pool.
  • Apparently Matt has a stuffed bunny named "Mr. Hippity Hop".
  • Yolei and Mimi at the bathhouse.
  • Ken bemoaning a terrible story. Given the author's known dislike for the original anime, one gets the feeling a similar scene led to the story's creation.

Chapter 28: Murky Affairs

  • Davis needing to give Cody a piggyback ride while crossing the swamp conjures a hilarious image. Same with the previous scene where Cody attempts to swim but just winds up with only his hair above water.

Chapter 29: Bugged

  • Davis complains about how Jun listens to weird music and his description of it sees TK agree. Given that Jun is obsessed with Matt and Matt is a jazz musician...
  • The pool game which sees Yolei smack Davis right in the gut with the cue ball and Cody handily win by ricocheting his shot into multiple balls in just the right order.
  • TK repeatedly wondering if something is real or not when they're at the hotel.
  • Davis is far too pleased after observing the other boys when everyone is in the bathtub.
  • Yolei's peeping is brought to an end by Patamon discovering the peep-hole and Davis putting his finger in it.
  • An expy book of Literature/Twilight shows up. Given Kari's and Gatomon's experiences with vampires, you could easily guess her stance on that work of "literature".
  • Davis's mangled attempt at summarizing Gullible's Travels.
  • Hawkmon knows his partner far too well, deducing that the hole in the wall meant Yolei was peeping.
  • It took Cody THIS long to realize Digmon was an insect.

Chapter 30: The Spider, the Flute, and the Mummy

  • In other display of rather poor observation, Cody fails to realize that he's the only one of their trio not to have his arms stuck to the web.
  • A bit of a meta joke, by Tai here makes it clear that he isn't all that worried about growing up. Contrast to how he is in Digimon Adventure tri.. Even better, this chapter was posted over five years before Tri was even announced.
  • What do Agumon, Gabumon, Biyomon, and Tentamon do after their kids and the younger gang go home? Run into the enlarged hotel to see if it has giant chocolates on the pillows. Child stage indeed.

Chapter 31: Tilt

  • Mimi's reaction to seeing Yolei's room is rather amusing.
  • Upamon ate a book. He thought it was a sandwich. What caps it off is Demiveemon asking how it tasted.
  • Davis practically has an aneurysm whenTK and Kari pair off to search the fairgrounds.
  • The other kids literally get pinballed around by Kari.

Chapter 32: Sink or Swim

  • Yolei does a great Velma impression after her glasses are broken.
  • Cody is rather insistent that he was meditating, not napping.
  • The reason Izzy's scanning couldn't find Gomamon was because he was deep sea fishing.
  • Davis once again lands them all in trouble when he taunts Arukenimon and Mummymon by saying Izzy is incapable of getting to the Digital World. Given that they're being held hostage in exchange for the Crests, the others are horrified.

Chapter 34: Downhill

  • Shurimon and Yolei pair off to participate in the snowboarding race. However, Shurimon's insistence on stretching first causes them to start late and then sees Yolei go flying down the slope on her own.
  • Kari is doing fairly well until an out-of-control Yolei rockets past her. What really sells it is Gatomon complaining that she's hitting the catnip when they get home.
  • Despite the rather excellent job that he's doing, it's the first time Matt's been on a snowboard and it's all he and Gabumon can do not to freak out.
  • Yolei's out-of-nowhere win.
  • Mummymon wins the award for "Spillage" thanks to his wipeout with Bluemeramon.

Chapter 35: Glittering Eyes

  • The cheerleaders have a favorite bathroom. *sigh* High School.
  • TK and Kari get a little snarky after Gargomon makes a speech about how it was digimon who defeated the Dark Masters.

Chapter 36: Black Enigma

  • Davis is hilarious put-out by Kari's concern over TK right after she's rescued.

Chapter 37: Concealment

  • Ken kicks the fragment of the Crest of Love into a train's engine and it literally starts flying.

Chapter 38: New Horizons

  • Class projects for the older kids turn into a bit of a fiasco as Sora accidently sprays water and winds up slipping and wrecking her project. Then Tai losses his grip on a bucket of water that he is swinging around to demonstrate centrifugal force and douses the back row
  • Davis spends a few minutes after practice fantasizing about Kari. Unfortunately, this means he isn't paying attention and a soccer ball kicked by Sora ends up smacking him right in the sweet spot.
    • It only gets funnier thanks to Tai's completely nonchalant attitude over the whole thing. And then the hilarity is capped off by Demiveemon asking Davis if he can eat his nuts.
  • Davis learning that his rendezvous with Kari is not the private affair he had hoped it would be.

Chapter 39: Chasing Shadows

  • Professor Takenouchi's comment about how he thought Sora changed because she had started dating is rather amusing given that she and Tai hook up less than a month later.

Chapter 40: Last Stop

  • The gang nearly getting flattened by the flying train became this after a similar event happened in Tri. I wonder if the people at Toei read fanfiction.
    • An added bit to this seen would be Tai and Sora's Suggestive Collision that starts off Kari's matchmaker scheme.
  • Demiveemon gets drunk. That is all.
  • Tai is a little twitchy going over to Sora's.
  • Davis and Yolei both thought several barrels of gunpowder marked with XXX were filled with porn.

Chapter 41: Reversal of Fortune

  • Kari is mystified as to why Tai would compare him and Sora to her and TK when she tries to convince him to ask Sora out.
  • Jun tricking Davis into selling half the tickets to Matt's concert.
  • The kids hijacking Mummymon's jeep. With Davis driving. He manages to hit the only tree in the middle of a barren plain.
  • According to Azulongmon, godly powers do not keep magazine subscriptions running. The kicker is how Tai just shrugs it off as a quirk of the Digital World.

Chapter 42: Humbug

  • TK smoothly talking Tai into asking Sora out on a date, a success he chalks up to being experienced in dealing with Matt
  • Jun fooling Davis into selling HER half of the concert tickets.
  • While it's probably not that funny considering how hard she's trying (and failing), Sora's attempts at baking cookies are worth a chuckle or two. Toshiko teasing her daughter also adds to the humor.
    • The recipe that ends up succeeding: Orange-flavored chocolate chip cookies. They are rather delicious.

Chapter 43: A Very Digi Christmas

  • The digimons' attempts to get gifts for their partners have to be read about to be believed.
  • When Davis's arms are full carrying Agumon and Gabumon, he has the latter shove his D3 into his mouth in order to port himself back to the human world.
  • While still very heartwarming, Tai and Sora's gabbled decision to make Matt's concert a date for them is also hilarious.
    • TK and Kari's own conversation about relationships is rather funny as well, if only for the Image Spot of Davis's possible reaction.
  • Mummymon's sheer delight about Christmas is only made funnier by Arukenimon's reaction to it.
  • Davis tries to offer Kari his arm. Demiveemon thinks its a quarter nelson. Tough break Casanova.
  • Hiroaki's crew once again have a hilarious couple scenes. The fact that they are explicitly described as the least useful just increases the funny factor.
  • Matt still thinks Jun is a loony, but admits that she has her perks when she helps extract him from the collapsed tent. It becomes even more hilarious when you remember the scene in the original where Jun comes to the conclusion Matt and Sora are an item because he saves her from falling debris (though this troper is still curious about the timeline of events and how concrete wound up falling from a tent).
  • Kari's attempt to give Agumon a Christmas bedtime story, only to mangle together most of the Rankin-Bass specials and The Polar Express.
  • Davis's Christmas plan; get some mistletoe and give Kari a Christmas kiss.

Chapter 44: Day of the Dead

  • Like Tai before him, TK makes a thoughtless comment in Gennai's presence. Like with Tai, Gennai reacts by putting him in a headlock.

Chapter 45: At the End of the Tunnel

  • Jun runs in to Matt and Sora patrolling. From her assuming they're dating, to squeeing over Gabumon, to Sora teasing Matt, the whole thing is both heartwarming and hilarious.
  • The aftermath of the group's battle with Marinedevimon as everyone is equally exasperated by being covered in ink.
  • Tai and Joe stop by Mimi's and their visit goes rather well, at least according to Tai, who remarks that they didn't get thrown in jail. This is either a great Call-Back, or there's a funny story involving the police.

Chapter 46: Sinking Spirits

  • Apparently, everyone but Davis remembered the clothing changes when they go into the Digital World and packed extra coats.

Chapter 47: Worthless Endeavors

  • Once again it's up to the older group to provide the levity while the younger kids are in the Dark World. This time we see them trying to spy on Arukenimon and Mummymon. From a car. With Joe driving. It's even better than the similar scenes in "canon" where they chase after Oikawa.

Chapter 48: Dark Corners of the Earth

  • At the end of the last chapter Jun called Tai to try to get Matt's number. Here she calls Matt and his first thought is that Tai had better not have been the one to give her his number.
  • Hiroaki Ishida is a bit of a Memetic Badass in-universe thanks to the stories his employees spread.

Chapter 50: Vows

  • As sobering as Ken's funeral is, Matt and Jun's interactions are as priceless as ever.

Chapter 51: Wildfire

  • While it's not particularly funny with the full context, a policeman running away calling Yolei a "hitodama" (think Japanese will-o'-the-wisp) is rather amusing.

Chapter 52: Up in the Air

  • Davis realizing he slept over at Yolei's. In her bed. With her (get you mind out of the gutter, not like that). And then his subsequent flight which see him slip down the fire escape, dangle from the rail, and plop into a snowbank. It's made more hilarious by the fact that it's not Yolei's parents who were coming in, but her siblings. Even when Davis wins, he's still the universe's bitch.

Chapter 53: Digimon World Tour

  • Joe and Gomamon's routine never fails to get laughs.
  • Yolei's family is accepting of her going off to globetrot and what's her father worried about: the expensive contacts that she's discarded.

Meta

  • A fair amount of analogies used are just plain hilarious.
  • If one has a dark sense of humor, then the fact that both TSWNT and Digimon Tri. both have former Digidestined as antagonists could be this. Especially since TSWNT began almost a decade before Tri did.
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