Digimon Adventure, the first season of Digimon’s long-running anime began airing in 1999, spawning numerous series that were sequels, standalone instalments, and spin-offs alike. Twenty-five years later, Digimon celebrates its 25th anniversary of animated television. To commemorate this milestone, we are counting down twenty-five of our favourite moments from Digimon Adventure. There are many great characters, battles, and drama across the franchise, but we’ll limit it to the original series (and Digimon the Movie).
25. The First Meeting
Our first entry on the list marks the start of the Digidestined’s journey. In the mesmerising first episode, seven kids – Tai, Matt, Sora, Izzy, Mimi, Joe, and T.K. – find their summer camp covered in snow. Their Tamagotchi-esque Digivices are then flung at them like miniature meteorites, before a water portal swallows them up. The seven find themselves in the Digital World, an alternate universe that was born from the computer age. Everything in it is technically made of data, including the colourful Digimon. The world as a surreal, dream-like art design, feeling incomplete and still being made.
Tai and co. meet their Digimon partners, who first appear in their cute “In-Training” stages. Much like Pokémon, they can digivolve into stronger forms, but are able to go back and forth between stages. Chased by Kuwagamon, the Digidestined are corned by a waterfall. The plucky Digimon confront their pursuers, digivolving into their Rookie stages for the first time. These partners serve as friends, pets, and emotional foils to the kids as they undergo character growth. The Digimon defeat Kuwagamon, but victory doesn’t come as easy when the giant beetle sends the kids plummeting down the waterfall in an exhilarating cliffhanger.
24. Machinedramon Gets Sliced Like An Onion
The final arc of the anime involved the Dark Masters, four powerful Mega-level Digimon who turned the Digital World inside out the create Spiral Mountain. Machinedramon was perhaps the most menacing; a tactical genius “built for total annihilation” according to Piedmon. He systematically tracked the Digidestined through his city-state before scattering them underground. But, their confrontation is brief and even humorous. WarGreymon single-handedly dismembers Machinedramon, slicing him into three pieces in a single stroke battle. Koromon then quips that he sliced the Dark Master apart “like an onion”. The English dub included a lot more humour and puns in dramatic moments, this being a classic.
23. The Baby Incident
The search for the Eighth Child in Tokyo is not an easy task for the Digidestined. One of their biggest challenges is sneaking around with their Digimon in broad daylight. In one hilarious scene, the kids board the city subway, pretending their partners are cuddly toys. A baby grabs Yokomon’s stem and gets a little too enthusiastic with tugging it. The enraged Yokomon screams at the baby to let go, rendering the entire subway train speechless. It’s one of the rare moments where the dub doesn’t insert music into a scene, playing on the comedy. Sora covers by staging a ventriloquist performance, before sending a stampede of eager customers off to Nerima to search for more “toys” like hers. In the years to come, finding actual Digimon merchandise in Japan wasn’t that hard.
22. Princess Karaoke
Mimi Tachikawa is either a character you love or can’t stand. Voiced by the late Philece Sampler, Mimi was depicted as a peppy, spoilt valley girl, hiding deep sincerity and pacifism beneath her shallow exterior. In the episode “Princess Karaoke”, Tai and Joe find Mimi living her dream as a princess. She was invited to awaken the sleeping ShogunGekomon using her singing voice, in return for her pampered lifestyle. Power went to Mimi’s head, bringing her worst traits to the surface. It is only through a pep talk by Sora that Mimi realises how terrible she is acting, promising to fulfil her promise to sing her heart out.
21. Joe Defeats Lord Bakemon
Joe Kido is the oldest of the Digidestined, a cautious worrywart who believes he must be responsible for the others, all the while moaning and groaning. His partner Gomamon is playful and laidback in contrast. In one episode, he, Sora, and their partners are stranded on an island occupied by masked dancers occupying a church. The dancers turn out to be the ghostly Bakemon, who plot to feed Joe and Sora to their master, Lord Bakemon. Joe is able to use a Buddhist chant to shrink Bakemon in size and power, allowing Birdramon and Ikkakumon to blow the ghost to smithereens. Compared to his other, more action-based heroics, Joe using his intelligence to defeat an enemy reflects his better qualities as a character.
20. Piedmon’s Keychains
Piedmon is the theatrical leader of the Dark Masters, a psychopathic pierrot with the humour of the Joker. Derek Stephen Prince, the most recurring voice actor in Digimon, riffed Tim Curry in his performance, using many theatre puns. Unlike the other Dark Masters, Piedmon took a more playful but frightening approach to fighting the Digidestined. By covering the characters in blankets, Piedmon transformed them into keychains. The kids are forced to flee through a series of circus stunts, captured one-by-one, until only T.K., Kari, and Patamon are left. Patamon digivolves into MagnaAngemon for the first time, rescuing the others, before banishing Piedmon through the Gate of Destiny.
19. Matt and the Crest of Friendship
Digimon has had a tradition of having brooding, troubled boys as part of the main cast. Matt Ishida is the first of these, a boy who acts like a cool lone wolf, but hides insecurities out of view. T.K.’s older brother, Matt struggles to protect and care for him, all the while dealing with the divorce of his parents. His greatest trait is friendship, looking out for others, even if he butts heads with them just as much. In “WereGarurumon’s Diner”, Matt finds himself doing penal servitude with Joe in a Digimon-run restaurant. Matt grows increasingly frustrated with Joe’s alleged mishaps, putting their friendship to the test. The entire affair is a scheme set up by DemiDevimon to neutralise Matt’s Crest of Friendship. When Joe defends T.K., Matt regards him as a true friend, allowing Gabumon to digivolve into WereGarurumon.
18. Puppetmon
Few villainous Digimon are sympathetic, save a few. The first was probably Puppetmon, the second member of the Dark Masters. A spoiled brat with an explosive temper, Puppetmon rules over a vast forest, where he likes “playing” with others. His biggest hurdle is that he lacks friends, a concept he misunderstands and rejects. He abuses and often kills his minions, who all hate his games. Amongst his highlights are his pun-infested battle with MetalEtemon, his kidnapping of T.K. who outwits him, and his manipulations to turn Matt against Tai. Puppetmon is warned by Cherrymon that the Digidestined’s bonds will be his undoing. It turns out he was right, being unable to beat the kids. Matt arrives, appropriately defeating Puppetmon, who pitifully dies in confusion as to how they won. Another version of Puppetmon appeared in Digimon Fusion, successfully becoming friends with Mikey Kudo.
17. Gotsumon and Pumpkinmon
Myotismon brought a vast army of Digimon to help invade Tokyo and hunt down Tai’s sister Kari. But, not all of them were there to obey the vampire lord. Gotsumon and Pumpkinmon went along for fun. In the episode “Out on the Town”, Matt and T.K. meet the two Digimon, who are enamoured with the human world, going on a fun rampage across Shibuya. Although the boys are annoyed with the duo, they are horrified when Myotismon arrives and kills Gotsumon and Pumpkinmon for their tardiness. This showed just how merciless and cruel Myotismon was, and the darker tone that Adventure would have going forward. The dub tried to play off the deaths as “banishment”, but further attempts at censorship were abandoned when the body count began to rise.
16. Matt vs. Tai
Tai and Matt butt heads a lot in the anime, even coming to blows on several occasions. The most dramatic clash comes during the battles against Puppetmon. Matt, feeling inadequate as a friend and big brother, went off in a huff. He meets Cherrymon, who manipulates Matt into believing that the only way to grow stronger is to beat up Tai. Matt and a reluctant Gabumon go along with this, leading to tense clash as Matt and Tai fight, whilst their Digimon do likewise overhead. This swiftly fractures the fellowship as the Digidestined look to all start falling out. Luckily, Kari gets possessed by a digital entity called Homeostasis, who provides some much needed exposition as to how the children were chosen to be the Digidestined. Afterward, Matt departs to do some proper soul searching, before returning to aid Tai and co. in battling Piedmon.
15. Myotismon
Myotismon is one the most recognised villains in the Digimon franchise. A charming but cruel and murderous vampire lord, Myotismon believes it is his destiny to rule the Digital World and cast Earth into darkness. To do this, he must find and kill Kari, the prophesized Eighth Child who will destroy him. Just about everything Myotismon does is wicked, from leaping out of a flying coffin in his first appearance, to seducing and biting unsuspecting women in Tokyo. He is eventually killed by Angewomon with a celestial arrow, but even that doesn’t stop him. But, a second prophecy reveals he will rise as VenomMyotismon, a Mega-level, who for whatever reason, has a smaller beast living in his crotch area! Even after his second death, Myotismon survives into Digimon Adventure 02 by possessing Yukio Oikawa, orchestrating the season’s events for his own resurrection as MaloMyotimson.
14. Leomon’s Death
Leomon is one of the most noble and heroic character in Digimon Adventure. His rivalry with Ogremon, brainwashing by Devimon, and surprise digivolution into SaberLeomon are amongst his highlights. Leomon dies battling MetalEtemon, promising Ogremon that their rivalry can return once he is reborn. This sparks Ogremon’s development from a villain to an honour bound anti-hero. Per the lore of Digimon Adventure, dead Digimon get recycled into Digieggs to be reborn in Primary Village. But, Leomon’s death kicked off what became a tradition in the franchise. Much like Optimus Prime kicking the bucket in every incarnation of Transformers, Leomon would perish almost every time he, or a variant, appeared in Digimon. Poor guy can’t catch a break.
13. Izzy Being A Good Son
Koshiro “Izzy” Izumi is the perfect character for the Digital World, drawn by insatiable curiosity and a need for knowledge. On the other hand, he is not much of a social butterfly, preferring his laptop compared to people. Izzy’s withdrawal is not from merely being an introvert, but because of his backstory. At a young age, Izzy discovered he had been adopted by his devoted parents, causing a rift between them. As such, Izzy plays the role of the perfect child, but isolates himself regardless. Out of all of the Digidestined’s personal hurdles, Izzy’s is resolved the most smoothy, learning his birth parents died in a car accident. Having lost their own child, Izzy’s adoptive parents took him in. The three make amends in a very moving scene.
12. Greymon vs. Parrotmon
This list would be incomplete without including Digimon: The Movie. Three separate films were mashed into one, made up of the short film called Digimon Adventure, the first season’s sequel movie Our War Game, and the 02 movie Hurricane Touchdown. The film(s) were directed by Mamoru Hosoda, who has since garnered his own impressive filmography, including Summer Wars, which took heavy inspiration from the Digimon movie.
One of the many highlights of the movie has to be Greymon versus Parrotmon. A young Tai and Kari befriend a Koromon; not the same character as Tai’s partner Agumon. However, he digivolves and becomes a gigantic, feral Agumon for some reason. Parrotmon then pops out of the sky, leading Agumon to digivolve into Greymon. Cue the Digimon theme song, and a short but sweet brawl between the two giants, culminating into Greymon wiping out both himself and Parrotmon. This fight acts as the linchpin for the Digidestined being chosen to save the Digital World.
11. The Music
One element of Digimon Adventure that must be praised is the superb music. Although the English dub rescored the entire series, the Japanese songs by the late Kōji Wada such as “Butter-Fly” are fan favourites. Another well known number is “Brave Heart”, composed by Ōta Michihiko and sung by Ayumi Miyazaki. The English dub released a wide variety of songs, all catchy in their own ways. The most well known as the Digimon theme song, performed by Paul Gordon. Other songs include “Let’s Kick It Up”, “Run Around”, “I’m Going Digital”, “Hey Digimon”, and “Here We Go”. Digimon: The Movie added a bunch of familiar songs to its soundtrack, including numbers from Smash Mouth, Fat Boy Slim, Less Than Jake, Barenaked Ladies, and Len.
10. Tai Finds His Courage
Tai Kamiya, our main protagonist and original gogglehead, undergoes one of the more complex character arcs. Going from a headstrong boy to a fearless and protective leader, Tai must overcome his greatest flaws. In the second arc, Izzy realises the Digidestined exist as data within the Digital World. Tai becomes overconfident, under the belief that they are now invincible. They mount a rescue of Datamon, unaware he is evil. Sora and Biyomon is kidnapped as a result. Tai give chase, but freezes at an electric fence that Izzy warns could kill him if he steps through the wrong section. Determined to make amends, Tai braves the trap, gaining his true courage. This allows Agumon to digivolve to MetalGreymon for the first time.
09. Sora’s Crest of Love
Sora remains my favourite Digidestined, a maternal, compassionate girl who carries a lot of care in her heart. However, she feels she is unworthy of love, at first remaining distant from her affectionate partner Biyomon. This stems from her broken relationship with her mother, who wanted her to learn their family business of flower arranging. Sora interprets her mother’s coldness as unloving. This drives a lot of Sora’s behaviour, looking out for her friends, but struggles when love is returned.
Sora’s self-doubts are put into motion when DemiDevimon claims her Crest of Love would never awaken. As Myotismon tries to separate her friends, Sora works against him, secretly helping the other Digidestined to activate their Crests. When Biyomon tries fighting for Sora, she begins to realise their own relationship is based on that with her own mother. This awaken Sora’s Crest, allowing Biyomon to digivolve into Garudamon and battle Myotismon. Sora’s mother would later team up with Biyomon to rescue Sora during Myotismon’s take over for Odaiba.
08. Angewomon vs. LadyDevimon
The battle between Angewomon and LadyDevimon is a brief but awesome scrap towards the end of the Dark Masters arc. Serving as the guard to Piedmon, LadyDevimon immediately targets Angewomon, leading to a hilarious fight. LadyDevimon swings Angewomon around by her hair. MegaKabuterimon tries to get in the battle, but Angewomon wants LadyDevimon to herself, leading to a round of censored slaps. Meanwhile, Tai and Izzy watch the fight in total astonishment, whilst Kari cheers for the witch’s destruction. Angewomon ultimately wins the fight. A different version of LadyDevimon appears as a member of the Daemon Corps in Digimon Adventure 02, leading to round two between the rivals.
07. SkullGreymon
Tai has to deal with more of his flaws, particularly his pride and impatience. To stand a better chance against their opponents, Tai tries to force Agumon to digivolve to the Ultimate-level. In a confrontation with Etemon, Tai and Agumon face off with a rival Greymon. Tai throws himself in harm’s way to trigger Agumon’s digivolution. It backfires, transforming Agumon into the terrifying SkullGreymon, driven entirely by a thirst for battle. The normal digivolving sequence is swapped out for a more unnerving one, with even the soundtrack distorting. SkullGreymon proceeds to exterminate the rival Greymon and then turns on his allies, before running out of energy and becoming Koromon. Tai carries severe guilt for a couple of episodes, learning to become more patient and caring.
06. The Battle of Odaiba
This entry could cover the whole of Myotismon’s invasion of Odaiba, but we are only covering the final battle against VenomMyotismon. This battle is significant for WarGreymon and MetalGarurumon appearing for the first time, after Tai and Matt are struck by celestial arrows of hope and light. The first Mega-level digivolution sequence is exciting, putting the Digidestined on equal ground with VenomMyotismon. The fight lays waste to Odaiba, but ends with the Digidestined defeating the vampire with the power of friendship and an energy blast to the crotch!
05. Home Away From Home
The most striking episode of the anime is “Home Away From Home”. Directed by Mamoru Hosoda, the episode has a different art and animation style compared to other episode; perhaps a deliberate choice since all other episodes have been set in the Digital World. Tai and Koromon were sucked through a vortex, winding up back in Japan. We are introduced to Kari, whose presence begins several subplots and mysteries, such as the time differences between the two worlds, and Kari’s memories of Koromon and the Digital World.
The episode is less action-focused compared to others, following Tai as he adapts to being back home, as well as trying to understand Kari’s connection to the Digimon. But, Digimon begin to appear in the real world, affecting it with their presence. Agumon has to battle Ogremon, before a portal opens to send them back home. Tai goes to follow, but Kari pleads with him to stay. Knowing that he can’t, Tai has to say goodbye but promises her sister that he will return home soon. It’s a very moving moment. Hosoda’s direction and unique take on the episode’s storytelling were a indicator for his future career as a filmmaker.
04. Patamon Digivolves into Angemon
Patamon’s first digivolution into Angemon is a landmark moment for Digimon. Fighting against a gigantic Devimon, the Digidestined are on their knees, with only T.K. and Patamon still standing. Patamon digivolves into Angemon, who swiftly gives his life to defeat Devimon, using the Hand of Fate to blast a hole right through his rival. Devimon is so badass that he just laughs his own death off, whilst a dying Angemon promises T.K. that he will come back. This is a pretty traumatic moment for the kid, being a defining moment for his life. Patamon is reborn as a Digiegg, but it takes some time for his return.
Angemon’s death haunts T.K. as he grows older. In Digimon Adventure 02, he discovers Devimon is still alive, but his data is absorbed by Ken Ichijoji to create Kimeramon. Normally a laidback and upbeat character, T.K. becomes cold and angry. He confronts Ken, mocking him, and then proceeds to beat the Digimon Emperor senseless, fuelled by his trauma. This is further explored in the soul-shattering third part of Digimon Adventure tri.
03. Omnimon
The second act of Digimon: The Movie is Our War Game, in which the Digidestined have to contend with Diaboromon, who was corrupted by a computer virus. He hijacks nuclear missiles and the only way to stop them is to wipe out his army of clones. WarGreymon and MetalGarurumon are no match for the constant barrage of attacks and are knocked out. Tai and Matt then defy the laws of physics, travelling by sheer will into the internet to help revive their Digimon. Through the power of friendship and emails, the two Digimon merge together into Omnimon, the first DNA Digivolution. In a stellar sequence, Omnimon obliterates the Diaboromon army, before finishing off the original in a nail-biting countdown sequence. Omnimon would remain a staple of the Digimon franchise, returning several times in the Adventure sequels and reboot. In other continuities, Omnimon takes on a more ambiguous role as a Royal Knight, serving the Digital World’s god Yggdrasil, often with misaligned loyalties or motivations.
02. Wizardmon’s Gift
The shot of Wizardmon’s tattered hat flying into view has burnt its way into the hearts and memories of those who watched it. Wizardmon was Gatomon’s closest friend, a kind but enigmatic character whose loyalty to Gatomon is greater than that to Myotismon. Realising early on that Kari is the Eighth Child and Gatomon is her partner, Wizardmon helps guide his old friend to realise her destiny. Their attempt claim Kari’s Crest of Light is thwarted by Myotismon, who takes Gatomon captive and casts Wizardmon into Tokyo Bay. He is save by the Digidestined, aiding in their rescue of Kari. But, he then makes the ultimate sacrifice by leaping in the way of Myotismon’s attack. The good wizard dies in Kari and Gatomon’s arms, triggering Kari’s Crest, and Gatomon’s digivolution into Angewomon. Wizardmon’s ghost survives within the systems of the Fuji TV station, reappearing to the Digidestined four years later to give them cryptic warnings of events in Adventure 02.
01. The Digidestined Say Goodbye
All journeys must come to an end, and ours fittingly ends with the departure of the Digidestined in Adventure’s final episode. When the Digital World reset, the kids learn they only have an hour to return home or they will be trapped forever. They then must say goodbye to their Digimon. Each pair reach the epilogue of their character arcs, all having touching scenes; with the exception of Palmon, who is too upset to say farewell with Mimi until the last moment. It is a bittersweet but moving finale for the anime, with the promise that we would reunite with the characters in the future.
What are your favourite moments of Digimon Adventure? Who are your favourite Digimon? Leave a comment on our Twitter feed.
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