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Digimon Universe: Applimonsters, better known as Appmon, is the forgotten digimon series, because it quite frankly barely counts as a digimon series. In fact digimon only appear in one episode. And that is exactly why it is the perfect season to start with when getting into Digimon.
Appmon is just a show I'd recommend on its own, even if it wasn't a digimon show. It's got a lot going for it. It's character's are fun, both larger than life and compelling. The characters start immature and flawed, before growing into themselves. Their character dynamics are honestly also unique and fascinating. The plot is well constructed with regular progression, ample foreshadowing and well-earned twists. It's one of the best shows in the franchise.
A lot of the best things about Appmon, are the reoccurring elements that I love about digimon to begin with. The human/monster relationships where the monster evolutions reflecting human growth, themes about humanities future and cross-cultural interactions, strong sibling relationships, and normal kids growing into heroes. Appmon is very much everything I love about Digimon, and thus showcases some of the best the franchise has to offer. But without, the baggage of being a digimon season.
Digimon can be intensely metatextual. While individual digimon stories may be complete unto themselves, its very common for digimon stories to make reference to other lore and themes. Glossing over them for the older fans. Things like Yggdrasil, Royal Knights, Jogress, File Island, Homeostasis as they appear. They are explained when relevant, sure, and often are excluded more than included but any given entry (Cyber Sleuth for example) may throw a whole heck of a lot of them at you without a whole lot of elaboration on the idea. Appmon almost completely strips out the metatext. It strips out the recognizable monsters and by extension, the virtual pet elements (thus the two baby levels and eggs), the character archetype shorthand's, and general digimon reference book references. No Leomon or Wizarmon variants to wave death flags. No virus, data, vaccine types nor armor or hybrid levels or x-antibodies potentially randomly dropped in without context. Because it's not that context is ever really needed: they'll explain if they are, but there is still the decades long, exceedingly over-complicated metalore cooking in the background of any given digimon series. Instead the Appmon being Apps means that any context on the creatures are rather self evident, their app type. The simple act of living in our modern society provides enough context. There are a lot of references to IRL AI culture, such as all the protagonists being seemingly named after AI, and the Dartmouth Workshop of 1956 being a plot point. Appmon has plenty of references and lore, it's just not overly all about Digimon. It doesn't completely strip out metatextual references to digimon, but it is kept subtle and unobtrusive. Haru has goggles because they make him more protag like, the kids find a phone booth, the kids are called "chosen children" once, and episode 44 does bring in Agumon as a video game but its non intrusive and isn't really used as any sort of shorthand. You can know that goggles that do nothing is a very extra character design element denoting protag status without knowing its a digimon thing. Old fashioned technology and modern kids is always funny. The kids were in fact chosen. And one episode out of 52 being a cute and heartfelt crossover is nothing. In short, Appmon doesn't have any of the baggage that might make a traditional Digimon season difficult to get into.
Which is probably the reason they made Appmon, well Appmon to begin with. Why they decided to start the franchise fresh so to speak to target the child (new) demographic while tri. targeted the older demographic. Appmon's come and gone, and they've abandoned that strategy, so newer entries of digimon still try to capture a new demographic while building on the old, so Appmon still remains as most stand alone entry of the anime.
But it is still very digimon in the ways that matter, meaning that if you DO like Appmon, you're very likely going to find at least one other season worth looking into. Logistically the season is a lot like Hunters and Ghost Game, with how evolution and the digital field works, the characters vaguely (with heavy emphasis on vaugely) resemble the Tamer's cast, the way the human digimon relationship's function resembles Savers imo. It's themes of humanities future and chosen one narratives are very Adventure. In other words it feels like a digimon season, because it works a lot like what came before it. Really, digimon seasons vary a lot. For the most part no two seasons are alike, there are very few things consistent in Digimon. Just a lot of things that reoccur frequently. So in the end, Appmon feels like a Digimon season, because it's just like a Digimon season in every way EXCEPT for the actual monsters.
Appmon is particularly similar in it's themes. Digimon often tackles themes of identity, alternate selves, destiny and responsibility, humanities evolution, humanities relationship with digital technology, and cross cultural exchange. So an entry may dive right into: what happens when you abuse your alternate self, or where does the locus of the self actually lie, glossing over the lighter "what would it be like to have an alternate self". Appmon covers many these themes too but it does so through the fresh lens, of Apps and realisticish (Heavy emphasis on the 'ish') AI, building its case from the ground up rather than falling back on typical digital world backstories. What makes an AI a fully fledged person, what is the point of being alive, how will humanity handle being overtaken by its creation, humanties newfound dependence on various AIs, and how can humans and sufficiently advanced AI coexist without one taking advantage of the other. Many of the same themes Digimon usually covers, but in the more specific context of a war between hyperintelligent super AI. Rarely are digimon significantly more intelligent than a human, but Appmon builds itself around the idea. Being Very Digimon, while also bringing something new to the table.
Appmon may have come out in 2016, but it's themes of AI transcending humanity are perhaps more topical than when it debuted. The original Digimon was on some level born out of the mystique of the new technology that the internet was in the early 2000s. As such, while Digimon generally toes the line between sci-fi and fantasy, it usually incorperates Sci-Fi aesthetics, but fantasy worldbuilding. Appmon's worldbuilding actually is heavily sci-fi, no implications of magic, but the themes and motifs of the story border still on mythological. Something closer to our modern understanding of technology. We know our internet, it's nothing special to us anymore. But we forget to a certain extent the power held by the internet in the modern day. Who is this power meant for? Digimon is in many ways, conceptually, a holdover from a bygone era, even as it seeks to stay modern. But Appmon is unapologetically modern, in a way that feels like it should have aged super fast, but somehow still feels contemporary 8 years later.
The other side of what makes Appmon the best to start isn't just that it's good to start with, it's that the other seasons are worse. To start with that is. I love them to death, and I don't think they are necessarily bad, but if you aren't already interested in what digimon has to offer, it might be a bit harder to sell. With how metatextual digimon can be you might think the first season would be the best place to start. I mean how could it not be. It's the first. Well, not exactly. Adventure is both the best and worst place to start otherwise. It is one of the cornerstones of the franchise, and so much of what comes after calls back to it. Adventure is a subtle story in a lot of ways that leaves a lot of the details to be parsed on rewatches. It's a genuinely passionate piece of art. In fact, the show is so detailed they many of the details didn't even make it in the show, with lore clarified in side materials. Most of these details aren't incredibly important, but they do provide insight into some of the shows otherwise confusing choices. Also, most were never officially translated into english. Also, the shows attention to detail left the show rife with opportunities for translation to be mishandled, leading to additional issues. Not to mention the 90s weren't exactly known for their faithful dubs, and this is true of Adventure too. Though Adventure itself still suffers a lot from metatext even outside of its own lore. Taichi's name and design are reused from the manga. File island, Server Continent, the idea of "raising digimon", the frequent presence of "garbage" digimon, and the disjointed evolution lines, are all borrowed from the general V-Pet lore. And ultimately Adventure is even more complicated by the franchises refusal to let it go. New releases, and cameos in other works are varying degrees of canon incompliant. Sometimes recent releases are insightful to the original work, sometimes they perpetuate misconceptions about the original work. Sometimes both. Sometimes its hard to say one way or another. To be clear, Adventure isn't really that complicated, itself. Very enjoyable even if you don't think too hard on it. But it's barely covering a whole maze of rabbit holes. I do recommend Adventure and 02, and it can ABSOLUTELY work as a first digimon series. But it does leave itself open to a lot of bad takes.
But, a familiarity with Adventure is sort of required to get the full effect of Tamer's, which serves as a sort of deconstruction of Adventure era digimon to a certain extent, or to actually understand Digimon Survive (a visual novel) which is in many ways a more mature retelling of Digimon Adventure. Otherwise Digimon series are either too unique in premise (Frontier and Xros Wars), and/or not very good (Adventure: 2020, Ghost Game) to warrant as a recommendation for a "first" digimon series. In all fairness, all digimon season are a perfectly fair place to start. None of them depend on each other to tell their story. I'd even argue that 02 is an acceptable place to start, if a baffling one. You don't need to know the meta-textual elements to appreciate their stories and characters and worldbuilding. That's how the franchise has survived through its multiple iterations. But when Digimon throws "Armor" level around casually, an artifact of an old storyline, it's kind of hard to argue that on some level digimon doesn't have an overwhelming history.
Savers is my second choice recommendation of a first digimon season. It too has its own metatextual elements of course, they are less overt and Saver's also just does its own thing worldbuilding wise a surprising amount. Otherwise its a solid story that utilizes typical digimon tropes, but doesn't explicitly call back to Adventure in its premise.
Of course there ARE other digimon media. The original Digimon media was the V-pets, which are fun, but have niche appeal. The same applies to the Digimon World games. Speaking of which, Digimon Games are generally not the best way to get into the franchise. They're mostly not very good, and I'd also add that Digimon games are even more heavily marketed to pre-existing digimon fans than the animes are. Digimon Cyber Sleuth is maybe the only exception, but even that very heavily pays homage to Digimon Adventure. Though, some of the manga, like Liberator or V-Tamer might be good places to start too.
There is one big problem though with Appmon as a first series. No English dub. Now, generally speaking the digimon fandom is plagued by bad translations. So many of the dubs generally kinda suck, so I usually recommend subs anyway, but I recognize not everyone can handle subs. There is a french dub, for those who understand French. I don't so I don't even know if its a good dub. If you're a dub only person honestly I recommend Tamers as a first season. It was the first one I finished. Its got a few issues that hold it back as an ideal first show for the uninitiated, but a solid story you don't actually need any context for. Adventure and Saver's dubs have problems imo that keep me from recommending them. (There IS a more supposedly more accurate SE asian dub of the early digimon seasons out there, but its harder to find + I haven't actually watched more than a few clips so I feel I can't exactly speak to its overall quality).
Ultimately, Digimon is the kind of thing where you can jump in anytime, and the kind of thing where there are plenty of fans who would be happy to explain the weird stuff. But you DO have to start somewhere. I just personally suggest Appmon.
Appmon is overall, just a solid children's tv anime on its own, as well as a fantastic example of what a digimon season can be. But without the 20+ years of baggage.