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  • Alternative Character Interpretation:
    • There's a lot of fans who debate on why Jyushimatsu's so infallibly happy all the time. One camp insists it's because he used to be (or still is) miserable or faced some type of hardship in the past, and is using his silly antics to hide it. Others insist that he's genuinely insane. And yet still others (jokingly) insist that he's on some type of drug. This even gets lampshaded by Choromatsu and Todomatsu in episode 13, with Totty theorizing that he may be hiding the most emotional darkness out of all the brothers. This ultimately comes to a head in episode 17, with the rest of the brothers trying to pinpoint the exact time Jyushi became like that, only to discover that he already was the way he is ever since he was a baby. This freaks them out enough that they decide to never talk about it ever again.
    • After "ESP Kitty", some looked back to Episode 2's roundtable scene and surmised that Ichi got angry at Karamatsu because he believed that Kara was mocking him like the rest of his brothers.
    • In a case of I Knew It!, Ichimatsu's unexplained hostility towards Karamatsu was commonly interpreted as jealousy of his confidence even before this was confirmed in an interview.
    • Some fans believe that rather than being oblivious to her selfish nature, the sextuplets love Totoko because she's as petty and shallow as they are.
    • It's common for Karamatsu to be portrayed with some sort of Inferiority Superiority Complex concerning his brothers, showing that he secretly doesn't take their annoyances with him well.
      • On the subject of Kara, many fans, including the creators themselves, debate on how "nice" he really is in comparison to his brothers. Some argue he's nice for the sake of being nice, and others (including the director) argue that he's nice because he likes the idea of himself being nice. However, no one will deny that he's actually done some genuinely nice things before, such as taking care of the ugly flower sprite in "The Life of Chibita's Flower", covering for Ichimatsu in "The Ichimatsu Incident", or punching Osomatsu to protect Jyushimatsu in "Letter".
      • His increased jerkassness in Season 2 hasn’t helped. Some fans think he acts like more of a jerk because he’s finally fed up of his brothers’ bullying and is starting to defend himself, while others think his asshole side is his true self coming out, dropping any pretense of being a “nice” person. Others still interpret him as somewhere in the middle; he's still nice at his core, but is by no means a perfect person across all situations.
    • After "Choromatsu and Ichimatsu", some fans have called out Choromatsu for his skeevy fantasies when confessing to Ichimatsu about how he isn't as proper as he seems, but others pointed out that while Choromatsu may be a pervert, he's unwilling to act on those fantasies. Another group has pointed out that the entire point of the exchange was to prove that the two brothers are painfully similar to each other despite their obvious differences.
      • This criticism of Choromatsu has reared its ugly head again following the release of The Movie. His desire to stay in the memory world to gawk at high-school Totoko and junior-high Nyaa-chan can come off as incredibly creepy to some fans. Granted Jyushimatsu calls him out on it immediately, but the unfortunate implication is still there.
    • In "Totoko and Nyaa 2", Nyaa makes an Instagramatsu post with hashtags saying things like "suffering" and "I'm really lonely". Is she really secretly Lonely at the Top, or is she just using those hashtags to get more attention from fans out of pity?
  • Alternative Joke Interpretation / Hilarious in Hindsight: At the time the first Mr Flag episode aired, Choromatsu's "OBAMA?!" yell was funny just because of the delivery. It was justified in that Hatabou knowing the US President was surprising. Due to Production Lead Time, the English dub came out years after Obama had left the office and quietly retired—Hatabou being contacted by a world leader makes much more sense than being contacted by a random former celebrity, making Choromatsu's outburst that much more confused.
  • Americans Hate Tingle:
    • Episode 10 was well received in Japan due to being a reprise of the iconic Iyami-Chibita team-up and having a tone similar to that of -kun. Its reception in the Western fandom was more... polarized, to be blunt, particularly among those who found the episode transphobic.
    • Dayon is usually regarded as either boring or unfunny in the Western fandom, especially after his portrayal in "Going North".
    • Among American Image Boards, the general consensus on the idol parody (skits, design, and all) is pretty negative, while it's received more positive reception in Japan. That said, some Western viewers did enjoy seeing them again in the Season 2 finale, and liked how they were written for it.
  • Base-Breaking Character:
    • Totoko in some circles. Either she's an entertaining Love Interest to the boys with an interesting personality all her own, or her Bitch in Sheep's Clothing nature makes her hard to like. Her lack of screen-time also attributes to this.
    • Jyushimatsu by the time the second half of Season 1 rolled around. While he is by no means losing popularity, his increased presence in some of the skits have led some to accuse him of being either overused or used uncreatively, which Iyami even lampshades in "Iyami's School".
    • Todomatsu is this as well. Viewers either hate him for his cattiness, or love him for that very same reason. His large amount of focus episodes are divisive as well.
    • Karamatsu has started to fall under this in Season 2. While some are happy seeing him be more assertive and less of a doormat, others feel that this has overshadowed his previous characterization as a kind and sensitive guy hiding beneath an obnoxious facade. Another subsection of fans feel like his taking a level in Jerkass is refreshing because it’s him finally revealing his “true” self. Yet another subsection of fans are fine with the change, seeing his shift in behavior as justified character development after being treated so roughly in the first season.
    • The Riceballs are big ones in Season 3, especially since they get almost as much screentime as the brothers themselves. Some fans loved their ongoing Story Arc about learning bad manners from the sextuplets, developing their own identities, and trying to make it big in the field of comedy, finding them to be effective Foils to the Matsus. Others thought they were obnoxious, unfunny, and one-note Cousin Olivers who took away screentime that could have been better used by the sextuplets. And still other fans Take a Third Option and hold that they were meant to be intentionally obnoxious spotlight-stealing new characters a la Poochie, considering how their Story Arc ends effectively getting banned from the world of comedy for cheating and being reduced to performing on the street for a bunch of schoolkids who tell them how much they suck.
  • Big-Lipped Alligator Moment: Ichimatsu turning into a Cat Boy during "The Melancholy of Osomatsu". Transformations made sense in other one-off gags since they were generally off the walls and had no bearing on the plot, but as this segment was just a straight up Slice of Life with completely normal elements, it felt a little out of place.
  • Bizarro Episode: The "Real Life Matsus" short from the Bonus Episode 3.5 is this. Instead of 2D animation, the whole thing is a silent short about live action actors with the Matsuno brothers' faces walking around town. That's it. Has no bearing on the rest of the show whatsoever.
  • Broken Base:
    • The series tends to flip-flop between Rapid-Fire Comedy episodes and more laid back works about the sextuplets maturing, and as a result, some audiences are put off by the switch in comedy between episodes.
    • The series was hit by this in the first episode too, where an unexpected change in art style (as well as an idol parody before escalating from there) literally divided viewers.
    • The tone and humor of -San is fairly different from that of -kun, meaning that many who read/saw -kun first favor the first series. Those people also tend to prefer the characterizations of Chibita and Iyami in -kun, since they were given more screentime to really stretch out their characters. Some watchers are also hesitant with -San because they're afraid of the legacy of the show upstaging -kun entirely.
    • The short "Going North" is kind of a polarizing one, as those who watched it either find it an odd, yet decent episode, or a waste of time that didn't utilize the characters presented well enough.
    • The controversy over the first episode being taken down and pulled from home release has left people split between those who find it appropriate and those who find it unfair. The circumstances occurring around the same time involving Japan's copyright laws just compounds the issue further.
    • The idea of shipping the Matsuno brothers with each other is a very divisive topic in the Western fandom. The disagreement over said ships has also lead to fans being either disgusted or amused by Ichimatsu's more questionable behavior towards his brothers in the latter half of Season 1 (such forcibly kissing Osomatsu and later taunting his brothers with towels in "We Caught a Cold").
    • Episode 13 garnered a split reaction from fans, especially since it was the first time in three weeks that the studio released new story content. "Sanematsu-san" was generally disliked by fans due to being overly dark and unfunny, but reactions are split on whether the other two skits made up for it or if the writers wasted their time on Alternate Universe material when they should have stuck to the character writing that made the series so well-liked.
    • Episode 16 had those who liked it due to developing Ichimatsu and Karamatsu's characters in the second half, and those who felt the episode was just one long string of Ho Yay jokes (made worse by the main characters' biological relationship). The idol segment during the first half also drew criticisms that Season 1 suffers from an over-reliance on Alternate Universe plots in lieu of actual Character Development.
    • If episode 16 threw people into a tizzy, "Osomatsu-san, Such As It Was" blew everyone else out of the water. One camp hated that the drama and tension built up in "Letter" didn't pay off because of the completely comedic tone of the finale, another camp didn't mind the lack of drama but found the episode weaker and less interesting than the ones before it, and then a third camp actually liked the episode and felt it was an appropriate send-off for the series.
    • The idea of a season 2 at all. While some were excited for it, others feared that the series would turn very shallow and pandering once it came back, due to the fandom and the merchandise influencing the show more and more (for example, the religion AU turning "canon" in a set of keychains).
    • Viz licensing the show, particularly because of the inevitable English dub. Fans are either excited about how the characters would sound in English (it helps that Viz/California-based dubs generally tend to be more well-received), or they are terrified that the dub would be a trainwreck that would lose all the charm of the original. Some fans are even a mix of both.
    • People are divided over Season 2. Some fans feel it’s as funny as, or even funnier than, ever, but others believe it lost the spark that made Season 1 so great. The increase in Cringe Comedy and toilet/vulgar humor in Season 2 is a special point of contention; either it’s bad because it’s starting to rely too much on shock value, or it’s refreshing because the show gets to do whatever it wants without restraint. Manga creator Reiji Yamada speculates that the increased Cringe Comedy and vulgar humor was an intentional response by the staff to dissuade the substantial fujoshi fanbase the show had amassed during the first season, which ultimately caused the season's viewership to steadily decline.
  • Character Rerailment: Season 2 started matching characters up to their -kun roots:
    • Dekapan's role as The Professor is expanded to having as much prominence as there was in the old serials.
    • The sextuplets still have their individual traits, but there's an upswing in synchronized gags and speech. Some skits even use the old method of having the brothers act together to highlight the episode's main focus.
    • Dayon is able to speak full sentences, and "Dayon and Dayon" even shows him in his more down-to-earth persona.
  • Crack Pairing:
    • Ichimatsu and Nyaa-chan have never talked to each other, let alone exchanged glances. The only thing they have in common is a cat theme and Ichi's secret fetish for cat girls. And sometimes, that's all that some fans need.
    • While his ship with Todomatsu makes some sense due to them being acquaintances, Atsushi has also been shipped with the other Matsus, who have never canonically seen him before.
    • There's also lots of ships for Matsus with different identities, for example Inspector Choromatsu from "Calming Detective" with Inspector Ichimatsu from Season 1 Episode 17.
  • Designated Monkey: Much of the abuse towards Karamatsu is this to a good number of fans, mostly due to it being downright excessive at points and that he almost never deserves it.
  • Die for Our Ship:
    • Totoko is a target of this to those who ship the Matsunos with each othernote  or any minor female character other than her.
    • On the slash side of things, Ichimatsu tends to get blasted by Kara/Jyushi or Oso/Kara shippers thanks to his fanon portrayal of being Karamatsu's Loving Bully.
    • Nyaa-chan's former fiance isn't very well liked from those that rather ship her with Choromatsu, Ichimatsu, Osomatsu or Totoko.
  • Draco in Leather Pants:
    • The Matsuno brothers often have their personality flaws downplayed in fanworks, instead having them come across as "cute" and "quirky" rather than acting like their goofy and immature selves. This, coupled with Self-Fanservice below, is especially prominent in shipping work and reader insert fics. This gets especially bad with Karamatsu and Jyushimatsu, as even though they're not quite as bad as the other brothers, most of their less savory moments are ignored for a "completely good" characterization.
    • Interestingly, Ichimatsu is a popular target for a completely different reason; while most viewers consider him a Jerkass Woobie, there's a surprisingly large subset of fans that blame his violent temperament entirely on the other Matsunos being either mean or neglectful towards him while they were growing up. Ichimatsu's voice actor, Jun Fukuyama, actually discussed the trope during one of his cast interviews, commenting that "ESP Kitty" resulted in a lot of fans romanticizing Ichi's personality.
  • Ensemble Dark Horse:
    • Nyaa Hashimoto only appears in a handful of scenes and doesn't even get many actual speaking lines, but she's still just as loved by the fans and often gets fanart. The second OP features Nyaa together with other secondary characters, but she doesn't show up in person until the penultimate episode of Season 1. She moves out of this trope once she becomes a regular cast member in Season 3.
    • The Distaff Counterpart versions of the Matsuno brothers immediately became popular after their short in episode 13.
    • Chibita is beloved by the western fandom due to giving some genuinely honest and decent advice in many episodes, as well as being quite possibly the only character who hasn't abused Karamatsu (at least not on purpose; in one episode he tries to help Karamatsu to find out his purpose in life and results are... not so good for Kara. Still, it didn't seem like Chibita was tormenting him for fun but genuinely trying to help) and actually treats him with kindness. "The Life of Chibita's Flower" just cemented this.
    • In Japan, Atsushi is one of the more popular one shot characters despite only appearing in a handful of segments, being Todomatsu's successful young friend who just so happens to look a little similar to the Matsunos, and is shipped with just about every member of the main cast.
    • The country girl from "Jyushimatsu Falls In Love" has no official name, spoke very few lines, and was important to the show for all of one episode. But her sweet nature, heartbreaking backstory, and adorable chemistry with Jyushimatsu won the hearts of many fans despite this limited role, and fan works featuring her started pouring in almost immediately after the episode finished airing.
    • Kinko from “The Cutie Next Door” has been almost universally liked by the fanbase immediately after her featured skit. Her cute character design, her likable personality, plus the fact that the Matsus (and even Totoko... though that one took some time) were perfectly comfortable around her made just about every fan want to see her again in the future.
    • From the movie, Ichimatsu's high school friend Yanagida. Being one of the few actively positive influences in his life and a somewhat conventionally attractive character by the show's standards, Yanagida quickly picked up a fanbase. He got so popular that he made the top seven in a series official poll, only a year after he debuted. He's often seen as Ichimatsu's "Atsushi" of sorts.
  • Fan Nickname:
    • "Matsus" for the sextuplets as a whole. On the same vein, most fans will call each brother by their "prefix" (Osomatsu is "Oso", Karamatsu is "Kara", and so it goes), though this is more for the sake of objectivity than actual nicknames. They're also called "Muppets" thanks to their wide mouths.
    • "MATSURISH"note  for the cast's F6 look during episode 1. The song they sing during this is similarly nicknamed "MATSU 1000%".
    • "Glorious Shift Leader" for Ichimatsu during his brief managing stint at Black Factory.
    • "14matsu"note  or "Tenshi" for Jyushimatsu. He's also sometimes called "Numbersmatsu", "Juicymatsu" or just plain "Juicy"/"Juice" in the English-speaking fandom.
    • The fandom also tends to call the sextuplets by a "Matsu" version of their voice actors' names (Choromatsu becomes Kamiyamatsu, Jyuushimatsu becomes Onomatsu, etc.).
    • Minor female characters associated with a particular Matsuno will be usually referred to as "[X]matsu Girls" (i.e. The two girls Karamatsu thought were checking him out, the girls on Todomatsu's date, Nyaa-chan, etc.)
    • "AV-chan"note  for the girl Jyuushimatsu spends time with during "Jyuushimatsu Falls in Love". In Japan, she's just referred to as "Jyushimatsu's Girlfriend", or simply "Kanojo-chan". She is also given the name "Homura" thanks to Jyushimatsu's "King-sized game winning home run" gag.
    • The couple that appears in the "Black Santa" short are often nicknamed "Couple-chan", "The Christmas Couple", or "Boyfriend-kun and Girlfriend-chan" by fans in the English-speaking fandom.
    • "Akamatsu" or "Defaultmatsu" for Osomatsu.
    • "Hivemind Mode" for moments when the sextuplets start creepily working in sync.
    • "Chadmatsu" for the "proper" Osomatsu seen in "Osomatsu-san Returns!"
  • Fan-Preferred Couple:
    • Karamatsu/Totoko, Ichimatsu/Totoko, and Osomatsu/Totoko. More than any other Matsuno brother, they've been consistently drawn together with her.
    • Choromatsu/Nyaa-chan is popular thanks to Choromatsu's rampant fanboying towards the idol. Helpsthattheofficialmerchandiseputsinsome shiptease.
    • Ichimatsu/Nyaa-chan, due to his love for everything cat-themed, cat girls included.
    • After the absolutely heartbreaking "Jyushimatsu Falls in Love", many viewers wanted Jyushimatsu and the country girl to be happy together. Some fans preferred him to be with Eitarou's mother from "The Eitarou Family", especially given she's wearing Jyushimatsu's hoodie later on in the skit.
    • On the slash/incest side of things: on Pixiv, two of the most popular ships seem to be Ichimatsu/Karamatsu and Osomatsu/Choromatsu.
    • Fans jokingly refer to the pairing of Dayoon/Dekapan as the One True Pairing due the sheer amount of Ho Yay in their segments together.
    • Thanks to their interactions in "The Karamatsu Incident", "Chibita and Oden", "The Life of Chibita's Flower", and especially "Letter", Karamatsu/Chibita has amassed a pretty sizable following in the Western portion of the fanbase.
    • Despite one half of the ship consisting of a very minor character, Atsushi/Todomatsu is actually pretty popular in Japan, with Atsushi often functioning as an Audience Surrogate of sorts.
    • The Matsuno Brothers/The Girly Matsus. It comes in multiple flavors, too; some ship the brothers with their specific counterpart, others mix it up a bit.
    • The popularity of the Totoko/Nyaa-chan ship has skyrocketed, mostly due to all the skits featuring them in Season 2, where their tension can easily be interpreted as Belligerent Sexual Tension.
  • Fandom-Specific Plot:
    • After the end of Episode 5, a lot of fans decided to include Karamatsu in the otherwise heartwarming ending of "ESP Kitty". Either the other brothers recognize that he's missing and include him in, or Kara just returns home to find his brothers worrying for him and apologizing for their earlier actions.
    • In general, anything involving the Esper Kitten's telepathy powers. In most situations he just makes the cast reveal grievances, untouched feelings for one another, or embarrasses them with their thoughts. It's Jossed though, since Ichimatsu revealed that the drug that made the cat talk in the first place had long since worn off in "Jyushimatsu Falls In Love".
    • A very popular plot in fanfics is explaining what happened to the Matsunos during high-school and how they became the NEETs they are now. While we don't get a full explanation for the latter, the former ends up as the backdrop of the Osomatsu-san movie.
    • Fix Fic where the country girl never leaves Jyushimatsu and the two become a couple. Or she returns to him after an indefinite time.
    • In Japan, it’s common to see Ichimatsu/Nyaa fics in which Ichimatsu meets the idol in the back alley he often goes to feed cats in, and she ends up being his Manic Pixie Dream Girl. Either the relationship is an unhappy one because of Ichimatsu's issues or he gets better.
    • In Japan, in fanworks, once Choromatsu and Nyaa get to know each other, they end up secretly dating (since idols dating/being in a relationship is illegal in Japan) with Nyaa wearing a hat (sometimes putting her hair up under the hat) and glasses in disguise. In the earlier fanworks, Choromatsu becomes Nyaa's manager. Thanks to the Fujio Rock event in Hesokuri Wars, it's not unlikely to see Band member Choromatsu (JADE) and Nyaa meeting each other and sometimes even teaming up/hanging out together.
    • In Middle/High school Nyaa-chan is a Meganekko with darker hair who crosses over with Choromatsu.
    • On the Nightmare Fuel side, there's the theory that Osomatsu is actually an only child and the rest of his brothers are figments of his imagination. This theory has been around since the days of Osomatsu-kun, but it's been gaining more traction thanks to the popularity of -San. It's implied that the "Sanematsu-san" segment was a subtle Take That! against the sheer amount of these fics.
    • A popular one is making the sextuplets supernatural beings, thanks to the appearance of Devil Osomatsu from the New Year's special. For some reason or another, Karamatsu is always portrayed as a priest. It's since become an Ascended Meme due to later keychains having a set based off of the common fandom versions of this plot. Choromatsu is usually shown as a god(dess) of some kind. Probably due to how high and mighty he seems in the show. Jyushimatsu is always seen as a angel thanks to be one of the nicest and thoughtful brothers. However, Ichimatsu is a toss up between being a grim reaper or an Ambiguously Human nun (of all things). Just like Ichimatsu, Todomatsu seems to juggle between a few persona's as well. Either being a witch, zombie, or vampire.
    • Thanks to the Colbert Bump the show gave to -kun's manga, it's popular to depict some of the manga's plots as events the Matsunos remember. Of particular note is Choromatsu having nightmares about the events of "Osomatsu-kun in 40 years" and Tougou from "The Terrifying Lodger" coming back into Osomatsu's life.
    • Thanks to early descriptions of Season 1 Episode 16, different variations on Ichimatsu stealing Karamatsu's glasses and the aftermath of someone discovering him. "The Ichimatsu Incident" is basically this plot, scene for scene.
    • Stagnating the Matsuno brothers' ages in order of birth, with Oso at his current age and the others being progressively younger, usually ending with Totty as a baby.
    • Plenty of "What If?" fanfics have arisen that continue the story after "Letter," where the events of the Bait-and-Switch finale either never happened or were All Just a Dream.
    • The couple from "Black Santa" becoming friends with Ichimatsu, mostly just to give him someone to talk to without falling all over himself. He's usually seen talking more with the boy in the couple.
    • Based on episode "Let's Become Independent". Sometimes an alternate universe on what if Choromatsu, Karamatsu and Jyushimatsu had to move out? They manage to do well on their own, getting their own house, with Choromatsu going to work while Karamatsu and Jyushimatsu taking care of the house. Choro and Kara tend to portray like 'parents' with Jyushi as the 'kid'....this can lead into shipping territory.
    • Fics about one of the brothers participating in self harm or even contemplating suicide is a popular one, with the suicidal party almost always being Ichimatsu for obvious reasons, though having it be another one (usually Karamatsu) is not unheard of. Interestingly, while this is often fodder for Hurt/Comfort Fic where one or more of Ichimatsu's siblings coming to help him out (whether or not they succeed is directly proportional to how much the author wants you to cry), it's just as common for this to slip into Dark Fic territory, as well as the occasional Deconstruction Fic, dissecting either Ichimatsu's self-loathing or, if Karamatsu is the suicidal one, Karamatsu's narcissism.
  • Fanfic Fuel: Fans who want to explore Karamatsu and Choromatsu's relationship further tend to consider Choromatsu telling Karamatsu he would take care of him if they couldn't remain in their house in episode 4 a good source of inspiration.
  • Fanon:
    • As a stylistic choice, some fans draw the Matsunos with eye colors that correspond to their motif colors, though it's a given that they all have brown eyes.
    • Ichimatsu and Osomatsu are commonly portrayed as the chubbiest of the brothers by both Western and Eastern fans, even though there's no indication that their bodies are really different from any of their brothers in the show. Similarly, Karamatsu is given the nicest figure because of his Narcissist personality, Choromatsu the skinniest due to Geek Physiques, Todomatsu the girliest, and Jyushimatsu the most muscular. Funnily enough, the Season 2 opening episode has the Matsunos (save for Osomatsu) portrayed exactly the opposite of the usual fandom body types when they're engaging with their fans; Ichimatsu is an almost emaciated walking corpse, Karamatsu ends up looking like a fat aristocrat, Choromatsu has the other well known Geek Physique, Todomatsu's body is "cute" in the way a mascot would be, and Jyushimatsu is the largest and fattest of them all.
    • Choroko is often depicted as shipping the male Matsunos together, despite her rather odd taste in pairings.
    • There are some that believe that Nyaa's true first name is Reikanote , with Nyaa-chan being a Stage Name. Along the same lines, the country girl is frequently named Homura thanks to Jyushimatsu's "king-sized game winning home run" quote. note 
    • There's a lot of fanart that depicts Akumatsu in Matsu form (black hoodie and a longer, shaggier version of their bowl cut).
    • Todomatsu being good friends with the three boys in his contacts he mentioned during "The Star of Hope"note . Atsushi is rarely portrayed as anything other than filthy rich.
    • Totoko being treated as the 7th sextuplet, with many of the brothers' clothes getting a fish-styled version in Totoko's color pinknote . The running idea over who gets the color orange in the sextuplets' lineup is split, though, as it has been attributed to Chibita, their parents, Nobita, and even Minimatsu of Shounen Bakabon.
  • Fridge Brilliance: Has its own page.
  • Friendly Fandoms:
    • Osomatsu-san and Doraemon fans tend to go hand-in-hand, at least in Japan. This has a lot to do with both Doraemon and the previous series coming out around the same time, too.
    • Osomatsu-san fans also tend to be Eddsworld fans. Hardly surprising, seeing as both works involve the wacky misadventures of a group of dysfunctional boys in color-coded hoodies.
  • Germans Love David Hasselhoff:
    • The anime in general had been very popular in the West LONG before it got licensed by Viz.
    • The episode “Iyami’s Counterattack” specifically was liked better outside of Japan, where it placed pretty low on "favorite episode" polls.
  • Harsher in Hindsight:
    • Remember how funny it was when Ichimatsu almost fell into a drunken rage after Karamatsu complimented him at the end of a long string of negative jokes made by his other brothers? "ESP Kitty" helps put that scene in another light.
    • Choromatsu was right to worry about how the cast handled "Osomatsu-kun Returns"— because of the episode's controversial nature and some old fashioned copyright infringement, the episode has not only been pulled from Japanese streaming websites and Crunchyroll, but also from its DVD/BD release.
    • Even from the previous anime series (also animated by Studio Pierrot) we get this. 1988 Series Episode 5 is titled "Chibita's Love. A Flower that Withers". Guess what happens in "The Life of Chibita's Flower".
    • Osomatsu being Alone Among the Couples in "Osomatsu-kun Grows Up" became harsher when the Drama CD "Osomatsu & Ichimatsu — “fortune-tellers”" came out. Turns out Osomatsu decided to visit a fortune teller because he was that worried about whether he or any of his brothers would get married in the future...
    • During "Let's Become Independent", Ichimatsu tells his mother that there's no telling what could happen to him if he's kicked out of the house. He isn't exactly wrong — because exactly twenty episodes later, he leaves the house and ends up homeless, penniless, and half starved to death.
    • In "Spring", Todomatsu is shown to be the most broken up about Matsuzou's heart attack. Imagine how hard he took it in "Osomatsu-kun Grows Up" when his dad dies choking on a fish bone at his fish shop...
    • The very beginning of "The Melancholy of Osomatsu" is funny the first time, since Osomatsu imagining that his brothers are playing cards with him (spot-on voice imitation of them included) is the whole punchline. After you've watched "Sanematsu-san", it can be a bit chilling instead, since it's almost the same thing but Played for Drama.
    • Nyaa-chan's boasting about her getting a hot and smart fiance in "Totoko's Big Panic" rings a little sad come Season 3, since she's not only broken up with the guy, but also left to raise his child alone.
    • Osomatsu's "I love you, Reika!" line from all the way back in Season 1 becomes this in Season 3, where a whole episode is devoted to Osomatsu and Nyaa-chan falling in love with each other, but never managing to commit.
  • Hilarious in Hindsight:
    • Totoko doing an idol show can garner a chuckle when you consider that Aya Endo played an idol in Macross Frontier.
    • Osomatsu wearing a vampire costume brings to mind a certain other series and a Japanese dub of films about vampires that Takahiro Sakurai worked on in the past.
    • "Please Let Me Sleep in Peace" reminded more than a few Japanese viewers of the infamous "Field Trip" sketch.
    • Fans started playfully calling Ichimatsu a masochist because of a particularly self-deprecating line in his version of "Six Same Faces" (Type-B)note . Guess who was revealed to have a secret masochism fetish a few weeks later?
    • The fact that Jyushimatsu has bug encyclopedias in his Porn Stash might remind a few viewers of #beesex.
    • Totoko having a massive Nosebleed looking at Ichimatsu's F6 form becomes this once you remember that Aya Endo likes that particular form of Ichi the most out of all of them.
    • The F6 in general are giant parodies of idols and Otome cliches. Color everyone surprised when there was an announcement that the actual Matsuno brothers were getting their own Otome game. And then come early 2016, suddenly they have pretty blatant Captain Ersatzes starring in another one of those games as possible routes. And to drive it all home, their pretty boy looks in the game not only look like the dyed hair versions of F6 themselves, but their downplayed personalities and appearances match the common bishiefied versions of the sextuplets!
    • Western fans like to joke that the brothers look like Muppets. Not only did the brothers end up getting hand puppets of them made as a special convenience store item, but now there's actually a short that features the characters as puppets.
    • The fact that Yoichi Fujita served as director for the show, given that the other show he was best known for directing had an episode where expies of the -kun era brothers squared off against the Odd Jobs gang.
    • In Episode 2 of the first season, Choromatsu makes it clear that he doesn't want to go through anything like "Osomatsu-kun Returns!" ever again. He's singing a different tune by the second season premiere, where he willingly participates in a similar episode.
    • The fact that their first idea was a Hotter and Sexier High School AU (with some romcom thrown in for good measure) comes down as this thanks to the 2017 debut of the high school romcom The Quintessential Quintuplets, a manga and anime about lazy quintuplet girls getting help studying from their beleaguered neighbor. The male lead having a somewhat Matsu-like hairstyle doesn't help. It also coincidentally resembles a common fanon concept where five of the brothers are cute girls, while one (usually Choromatsu or Osomatsu) is male and has to put up with his sisters' screwball antics.
    • A lot of the genderflipping fanart is rectified in the third season opener, where one of their more "diverse" Matsu groups are more or less girl versions of them who similarly can only be told apart by hairstyle.
    • Choromatsu was devastated when he learned that his idol was once married, has a child, and is falling in love with his shit eldest brother. This should have been a Tear Jerker, but becomes hilarious when one knows that a gossip magazine revealed in 2016 that Choromatsu's voice actor, Hiroshi Kamiya, had been married for serveral years and had a child already.
    • The show's first sketch is F6, a parody that has the Matsuno brothers as a group of hot idol singers. In 2022 a live-action adaptation of Osomatsu-San is to release, starring the Japanese idol band Snow Man.
  • Ho Yay: The series has a mostly male cast, the protagonists are sharing the same bed (the fact that they're brothers wasn't really a stopper), and they invoked this trope during the F6 stunt, as it was one of many clichés they were trying out to make an audience. Of course they would follow up on it, by accident or not.
    • Chibita initially didn't want to join Iyami in his Rental Girlfriend scam, but he agrees to it after Iyami comments that he'd look cute in a skirt.
    • Dayoon and Dekapan in "Love", where they spend all of Christmas Day together and buy each other presents, then go to what appeared to be a love hotel. The next time they're seen together, they wear what appeared to be traditional wedding clothes.
    • Ichimatsu instigates this twice in "We Caught a Cold". First, he decides to transfer his cold to Osomatsu (for blowing their money on pachinko) by French kissing him. Then, he makes his brothers beg for cold compresses when he's feeling better. The dub makes this worse— Ichimatsu sounds way more suggestive than the original version, and makes the other brothers call him daddy.
      Choromatsu: That wasn't taking care of us, it was obedience training.
    • The brothers regularly invoke this again as F6 in "Matsuno Matsunan" in order to defeat their enemies.
    • "The Ichimatsu Incident" ends with Osomatsu walking in on Karamatsu and Ichimatsu in a very, erm, suggestive pose.
    • In the Doramatsu Drama CD (Bar), Jyushimatsu and Choromatsu had sex. It was supposed to be an alternate universe, but Choromatsu ended up breaking the fourth wall.
  • Hollywood Homely: Nyaa-chan is apparently rather plain, at least according to Osomatsu. It seems to be a matter of opinion since she is an idol and clearly has many fans, and Choromatsu thinks she's cute.
  • Hype Backlash: Has had it for a while in Japan, in part because the show was a marketing giant and was everywhere during its explosion in popularity.
  • I Knew It!: Those who predicted episodes 24 and 25 of season 2 would be a redo of "Letter" and "Such As It Was" had no idea how right they were.
  • Incest Yay Shipping: A good chunk of the fandom is rife with it. On Pixiv, part of the fanbase has taken to shipping the Matsuno brothers together, either based upon their original relationships in the previous series (i.e. Osomatsu/Choromatsu because of their closeness in the original series), any present day interactions, or just out of a desire to see them together.
  • Jerkass Woobie:
    • Ichimatsu, thanks to the events of "ESP Kitty". He's not as outgoing as the other brothers and doesn't have a very high opinion of himself. Deep down, he feels left behind by how much progress his brothers made socializing because he finds himself unable to accomplish that, and that he doesn't deserve friends as a result. That being said, he's still kind of an asshole and does some pretty cruel things to his family sometimes.
    • Osomatsu through all of "Letter". He refuses to congratulate Choromatsu on getting a job, has a shocking Kick the Dog moment when he literally kicks Jyushimatsu out of anger due to his own frustration (and it's implied he also punched Todomatsu for reprimanding him later) and doesn't part with any of his other brothers as they leave one by one. His unusual attitude is a stark contrast to that of his own brothers, who all support each other in graduating from their NEET lifestyle. But the viewers clearly see Osomatsu's true reason for so much bitterness: despite his complaining and saying otherwise, he truly loves his siblings and is hurting since they're parting ways for the first time. The shot of Oso sitting by himself in the room where all sextuplets used to gather is a definite Tear Jerker and makes it extremely hard not to feel sorry for him.
    • Todomatsu, as well. Yeah, he's a Social Climber and not really nice about it, but the main reason he acts this way is because he's tired of living in the shadows of his older brothers. "Star of Hope, Todomatsu" reveals that he does care a lot about his brothers, and even though he blames them for his troubles, he wants to help them improve their lives as well as his own. The fact that he's easily scared and can't do certain things by himself (like use the bathroom in the dark) also contributes to his Woobiness.
      • “Osomatsu and Todomatsu” took that Woobiness up to eleven. First, Osomatsu ruins their chances with a couple of women by blurting out highly inappropriate and uncomfortable remarks, then Todomatsu humiliates himself trying to cover for Osomatsu’s mistakes. Then, he gets completely overshadowed by Osomatsu despite the latter being completely crude and crass, and he goes home by himself (without the girls or even his own brother noticing) utterly broken. Even fans who usually don’t like Totty admitted to feeling bad for him after this.
    • Iyami of all people gets hit with this. He’s sly, self-absorbed, and incredibly greedy to a fault, but “Iyami, Alone in the Wind” shows that he has a caring side as well when he looks after a poor little blind girl (granted, this is an AU episode, but still...). The lengths he goes through for the girl, from working to the point of near-immobility, to breaking down in tears out of desperation, to actually getting incarcerated in his attempts to help her, makes you want to give the poor guy a hug. By the time the episode reaches its Bittersweet Ending, he has been thoroughly Woobified.
  • Launcher of a Thousand Ships:
  • Like You Would Really Do It: Even if the twist detailed below in They Wasted a Perfectly Good Plot didn't go off, there was no way the show would end itself letting its famous sextuplets go their separate ways.
  • Memetic Mutation:
    • The way Jyushimatsu reacts to receiving Shonosuke during the "Delivery Skit" sketch note  became a common way to refer to the man, and he's often shown with Jyushimatsu as something of a living prop/pet. Japanese viewers also used Jyushimatsu's hug from the same scene as a transparent image so he can hug whoever the user likes the most.
    • On some American Image Boards, a screenshot of Choromatsu sweating nervously while he thinks "We're not okay at all" became very popular.
    • Pears.note 
    • Go to bed, Karamatsu.note 
      • Fuck off, Totty.note 
    • Karalos.note 
    • TOTTY.note 
    • OBAMA! note 
    • "Anyways, here's Iyami bathing in cum."note 
    • On Nico Nico Douga, ヤバイヤバイヤバヤバーイ. note 
    • *(does [x]), but in a sexy way* note 
    • Quite a few Osomatsu-themed Twitter accounts decorated their icons with the photo frame used in Japanese funerals after the events of both "The Ichimatsu Incident" and "Letter".
    • PRAY FOR ICHIMATSU. note 
    • Iyami's "SHEEEH!", which had been a meme previously in the -kun era and got a reinsurgence thanks to this series.
    • "Who the fuck is Karamatsu" note 
    • Chorgus. note 
    • "Let Fappymatsu be Happymatsu." note 
  • Memetic Loser: Oh, Karamatsu. The fact that his charm fails him at every corner is bad enough, but in addition to the Never Live It Down moment detailed below, he's now seen as the punching bag for his brothers and some of the other cast members.
  • Misaimed Fandom: A cast interview reveals that "ESP Kitty" was supposed to be exaggeratedly feel-good so that the Comedic Sociopathy joke at the very end would work, but viewers ended up misinterpreting the whole thing as genuinely heartwarming instead.
    • This response was repeated after the abrupt and anticlimactic conclusion of "The Letter"'s plotline in "Osomatsu-san, Such as it Was". Word of God has gone on record stating that "The Letter" was mostly done as a setup for the punchline at the beginning of the finale, and was once again meant to come off as overly dramatic and uncharacteristic of the series rather than be taken seriously. In general, the darker and more emotional sides of the show's Cerebus Rollercoaster elements are almost always Played for Laughs by the staff, but taken very seriously by a large percentage of the fandom.
  • Misaimed Merchandising: The show does have a child fanbase, after all, but it's not quite for them. Although it can be argued that the toys are meant for adult collectors, that doesn't quite explain the official T-shirts and hoodies that come in kids' sizes.
  • Moe: All of the brothers are seen as this by some fans, but the ones who get called such the most are:
    • Jyushimatsu because of his childlike attitude, sweet personality, and hand-hiding sleeves.
    • Ichimatsu; while not being the most pleasant person around, actually invokes this in audience members due to being the most "relatable" and because of his huge fondness for cats.
    • Karamatsu's Butt-Monkey status has him put under the "want to protect" kind of moe for some viewers.
  • Nausea Fuel: The Sextuplets (unknowingly) eating human flesh, served by Hatabo, made from his staff.
  • Never Live It Down:
    • Karamatsu faced the wrath of a drunk Ichimatsu for a grand total of once at the time Episode 2 aired, but that was more than enough for some fans to start making fanart of their interactions boiling down to Karamatsu doing something that Ichimatsu doesn't like and Ichimatsu beating the living daylights out of him for it. That said, later interactions confirmed that Ichimatsu dislikes Karamatsu.
    • Ichi trying to take a dump on a table at Sutabaa has been referenced so, so many times by the fans. The fact that the gag was repeated in "The Star of Hope, Todomatsu" didn't help matters.
  • One True Threesome:
    • On Pixiv, most shippers like Ichimatsu/Karamatsu and others ship Jyushimatsu/Ichimatsu, then some artists had decided to ship the three together instead of turning it into Ship-to-Ship Combat. After Karamatsu and Jyushimatsu's song time, the idea of a threesome gained followers (same occurred to Karamatsu/Jyushimatsu).
    • Despite being at first a shipping way to round out the six brothers, Osomatsu/Choromatsu/Todomatsu also got more fans after "The Calming Osomatsu" skit. Got more fans and turned stronger with the airing of "Choromatsu Rising".
    • The younger brother trio of Ichimatsu/Jyushimatsu/Todomatsu and the older brother trio of Oso/Kara/Choro are also rather popular. There also Kara/Choro/Jyushi, Oso/Choro/Ichi and Kara/Choro/Ichi.
    • In terms of hetero trios, Choromatsu/Nyaa-chan/Ichimatsu Karamatsu/Totoko/Ichimatsu and Osomatsu/Totoko/Karamatsu are popular among fans.
    • On the crack side of the spectrum, there are quite a few fans who like to ship Ichimatsu with the couple from the "Black Santa" sketch. The ship gained slightly more momentum after their cameo in "Letter", helping a homeless and possibly starving Ichimatsu.
  • Periphery Demographic: Because this show is a sequel to one of Japan's most well-known manga series, the show quickly gathered up a wide audience, but what most people were surprised about was the large fujoshi fanbase.
  • Ron the Death Eater:
    • Todomatsu, it seems. He may be a two-faced Social Climber, but a few episodes have portrayed him sympathetically and he really does care about his brothers. This does not stop some fans from claiming he is literally Satan (whether they're joking or literally signifying their detraction).
    • While he doesn't quite get it to the extent Todomatsu does, Osomatsu sometimes falls under this (his actions in "Letter" certainly didn't help matters). In some fan works, he's portrayed as the villain, his flaws blown out of proportion to make him seem more cruel than he actually is in the show. Often times, the blame for his brothers' dysfunction is placed entirely on him, without taking the others' faults and shortcomings into account.
  • Seasonal Rot: In stark contrast to the overwhelming Sleeper Hit success that was the first season, the second season experienced considerably less fanfare. This is generally attributed to the more mean-spirited tone of the second season's episodes compared to the first's. While it's generally agreed that there was a drop in quality from the first, whether the season was still good in its own right or a veritable bomb is a topic of contention.
  • Self-Fanservice:
    • The Matsunos have their fair share of works that portray them as their round and cartoony selves, but there's an equal amount of works going around that portray them with realistic proportions and try to make them look more conventionally handsome. The Matsunos already have such a form thanks to the F6 stunt, but this trope refers to their actual selves being drawn this way. It's worth noting that the brothers do have some official fanservice in the way of dakimakura or even gravure shoots, but the official material is relatively tame compared to the hyper sexual designs fans made in response.
    • The Girlymatsus look almost exactly the same as the actual Matsunos, but that doesn't stop people from making them all gorgeous.
    • Todomatsu in particular gets this a lot. It helps that his F6 form is so cute that even straight male fans find it adorable.
    • Evilmatsu makes one real appearance, and it's as a big, black, shadow monster with no discernable features. Following his debut episode, most fanartists decided to draw Evilmatsu as a Matsuno variant like Godmatsu, but this time with bloodshot eyes and fangs.
  • Sequel Displacement: More well-known than Osomatsu-kun outside Japan, as most countries didn't get exports of any Osomatsu-kun series until after Osomatsu-san, and even if they did it's unlikely most fans remember it as much as Japanese viewers. The first episode makes it clear that the series is a sequel, however many non-Japanese fans simply think they're making fun of 1960s anime in general. Many jokes go over peoples heads because they aren't acquainted with the older series (Osomatsu-san is essentially what Dog Sees God is to Peanuts—a sequel of a family friendly work where everyone is older and the jokes are more adult oriented).
  • Ship Mates:
    • Since the most popular ships are Ichimatsu/Karamatsu and Osomatsu/Choromatsu, there's a good chance that you'll see fanwork that contain both pairings, with Jyushimatsu/Todomatsu to round out the six. Alternatively, Jyushimatsu/Ichimatsu shippers can opt for Todomatsu/Karamatsu.
    • In a lesser extent, there are those who ship Ichimatsu/Karamatsu, Osomatsu/Todomatsu and Choromatsu/Jyushimatsu due to their close theme colors and the interesting, refreshing dynamic of the latter two. Also helps that they teamed up as duo bands in the gum ad.
    • Those who pair off Jyushimatsu and the country girl often have Ichimatsu/Choromatsu and Nyaa-chan or Osomatsu/Karamatsu and Totoko together.
    • To the shippers who like both BLMatsu and non-BLMatsu pairings, the most popular lineup is Osomatsu/Choromatsu, Ichimatsu/Karamatsu, Jyushimatsu/the country girl, and Atsushi/Todomatsu.
    • Shippers who highly dislikes Osomatsu/Choromatsu and Ichimatsu/Karamatsu and feel that both pairings are abusive and/or unworkable, settle with Karamatsu/Choromatsu and Osomatsu/Ichimatsu, instead.
    • Fanworks featuring Karamatsu/Choromatsu have a good chance of Jyushimatsu/the country girl popping up as well.
  • Ship-to-Ship Combat:
    • In the Western Fandom, "Karabita" (Karamatsu/Chibita) shippers vs. people who ship Karamatsu with any of his brothers. Many Karabita shippers dislike the incest ships because they are disgusted by incest, while the incest shippers feel that Karabita shippers only ship it because they're just desperate to have a ship that isn't incest. There are beginning to be more fans that ship (or at least, tolerate) both but the tension is still there.
    • This not only affects Karabita, but the other non-BLMatsu ships as well (except Jyushimatsu and the country girl, which seems to be universally liked). Ships like Atsutodo (Atsushi/Todomatsu) or Ichimatsu and the Christmas couple have come under fire by BLMatsu fans, suggesting the pairings simply glorify one-dimensional "boring" characters with little to no personality (to the point that some don't even have names, in the case of the Christmas couple) that normally audiences wouldn't give a crap about; and that people just ship them because they're terrified of incest. It's come to a point where the fandom divides itself clearly by their preferences in ships and they're actually stated in the Osomatsu fan blogs/accounts/social media that are out there.
      • The matter of ships is a big debate in the Osomatsu fandom. Most of the BLMatsu fans admit that while it may seem gross, the Matsunos are the only characters in the show with a proper personality that you end up caring for, therefore you'd want to see them together; while the Matsunos x Supporting Cast admit that while most of the secondary characters are underdeveloped, they would prefer that a million times over incest. Then there's the third/fourth camp that doesn't like either options and resort to either shipping the boys with their own Original Characters/Reader fics or simply not shipping at all. There's a side that likes to ship the boys with their Girlymatsu counterparts, but that seems to be more appealing to Japanese fans than Western ones.
  • Shocking Moments:
    • The entirety of (banned) 1st Episode; Cameos & Copyrights everywhere.
    • The climax of "We Caught a Cold", where Jyushimatu multiplies until he's microscopic, enters everyone's bodies, destroys the virus, and then turns all the brothers into copies of himself.
    • The last few minutes of "Iyami's Counterattack", which features a major Animation Bump and a large-scale battle between Iyami and Osomatsu that eventually culminates in everyone coming back to life and then murdering their competitors via Gory Discretion Shots.
    • Karamatsu punching Osomatsu for hitting Jyushimatsu and getting in the latter's face in a fit of anger in "Letter". What Osomatsu does in itself classifies as this, but at least you see it coming, since his frustration was clearly building up during the skit. Karamatsu's outburst on the other hand was completely out of the blue, especially coming from him.
  • Theme Pairing: Crack Pairing Ichimatsu/Nyaa-chan have never talked to each other, let alone exchanged glances. The only thing they have in common is a cat theme and Ichi's secret fetish for cat girls. And sometimes, that's all that some fans need.
  • They Wasted a Perfectly Good Character: Some fans walk away from -San disappointed that Iyami isn't nearly used as much as he was back in the day, despite having episodes that had pretty positive reception (Iyami's Counterattack, Iyami Alone in the Wind, Iyami & Chibita's Rental Girlfriend). "Iyami-san is Troubled" acknowledges his lack of use and his dated status, but the producer straight up admits that he doesn't know where to take the character now and that it's too late to change anything, given the second season wrapped up not even two episodes afterwards.
  • They Wasted a Perfectly Good Plot: The latter half of "Letter" has Choromatsu getting a new job and moving out, the brothers gradually moving out and trying to live new lives, and it ends with a Cliffhanger as Osomatsu receives the letter that Choromatsu had written earlier, making it one of the biggest Tear Jerkers in the series. Then comes the Season 1 finale, where all of that gets dropped in 2 minutes and it just becomes another gag episode. However, according to Word of God, this plot was meant to be wasted all along. That being said, fans weren't as unforgiving when the stunt was repeated with the "Spring"/"Osomatsu-san in Hell" two-parter in Season 2; part of it was because of remembering what happened the last time, and part of it was because the wacky second half was kicked off by outside interference rather than deliberate sabotage.
  • This is Your Premise on Drugs: Cracked called it It's Always Sunny in Philadelphia on acid.
  • Too Bleak, Stopped Caring: A common complaint with the second season is that humor grew considerably more mean-spirited and crass compared to the first. Reiji Yamada speculated that the change of tone was intentional in order to push away the Fujoshi fanbase that the show had built up, and that this unintentionally contributed to Seasonal Rot instead.
  • Unexpected Character:
    • Most fans did not expect the F6 designs from "Osomatsu-kun Returns!" to show up ten episodes later without warning, especially since by then the episode had already been taken down from stream sites. Even more so when they appeared in episode 3.5 and "Matsuno Matsunan". Since these episodes, they've become semi-recurring characters.
    • Season 2 has had plenty of this. First, there was Episode 5, where Delinquent!Todomatsu from the “Schoolmatsu” skit in Season 1 is seen hanging around with Jyushiko. Then, the Girlymatsus make another appearance in Episode 7 as elderly women. And then, Episode 8 has the Girlymatsus (minus Jyushiko) make yet another appearance in “Jyushimatsu and the Dolphins” as dolphin trainers.
      • While the Girlymatsu cameos were unexpected, fans were absolutely floored to see the country girl return for “Jyushimatsu and the Dolphins.” Granted, it may have been more of an AU version of her than the actual character we saw in Season 1, but to say that nobody saw this cameo coming would be a massive understatement.
  • Unintentionally Sympathetic:
    • Karamatsu was always intended by the writers to be seen by the audience as a cringe-inducing, self-absorbed phony who only ever does good deeds to stroke his own ego, but his portrayal in the first season generally caused them to sympathize with him much more. This had the additional effect of making several of his over the top and insincere "considerate cool guy" gestures get taken seriously, which, in conjunction with multiple Pet the Dog moments of him showing genuine kindness to others, caused fans to latch onto him as the Token Good Teammate among the brothers, as well as one of the show's biggest Woobies. Season 2 seems to have made an effort to undo this, as Karamatsu's Butt Monkey status has been reduced significantly in order to place more emphasis on his more negative traits.
    • In Mr. Osomatsu in Hell, King Enma is very quick to decide that the sextuplets should be sentenced to hell. While this would be a fair call in an earlier episode, this episode is a continuation of Cherry Blossoms in which the brothers help make the stay better for their hospitalised father and aim to support themselves to ease the burden for their parents. As a result, the judgement comes off less like a karmic fate and more like a sentence from an overly harsh judge who denies the siblings were on the path to atonement.
  • Unpopular Popular Character:
    • Despite being seen as a general nuisance to his family, and despite his inability to pick up any girl thanks to his Mr. Imagination/"cool guy" act, Karamatsu nonetheless became the underdog of the Matsuno household and is just as popular as resident fan favorites Jyushimatsu and Ichimatsu. The fans still give him shit, but it's more because of the way the story treats him than anything else.
    • Ichimatsu is the only brother that everyone (including Ichimatsu himself) said was unlikely to get anywhere in life, and his antisocial and depressing nature make him nigh unapproachable if you're not a Matsuno. Nevertheless, across the board he seems to be a very well liked Matsuno brother, and many often express sympathy and love for him because of his funny moments and because they can relate to him in some way.
    • Iyami complains in "Iyami's Counterattack" that he should be the protagonist because he's historically been the most popular character. While he's an incessant liar, this is actually true; Iyami and Chibita were consistently the surprise breakout characters that eventually took over both the original manga and first two Osomatsu-kun animes.
  • Vanilla Protagonist: Osomatsu by a long shot. The rest of his brothers have standout quirks that make them recognizable, with Todomatsu being the only one who's even slightly similar to him (at least, until "Todomatsu and the Five Demons" established Totty as a social climber). Oso's most recognizable quirk? His relationship with his brothers and his greediness, which is a trait all of the brothers have anyways. Tropes Are Not Bad, however— his connection to his brothers is what makes Osomatsu well liked, especially after his reasonable moments in more dramatic episodes.
    • Lampshaded in episode eighteen, where the announcer says his popularity is surprisingly low and he's the only Matsuno brother the audience throws stuff at.
  • What Do You Mean, It's Not for Kids?: While the original manga is a Shonen and the characters in -San are still drawn as wacky and cartoonish as it gets, the anime airs late at night in Japan and most episodes have enough sex/nudity jokes that wouldn't let it pass as a kid's show. The Caught with Your Pants Down scene in Season 1 Episode 13 actually caused some problems with censors because of this.
    • In addition, Hulu Japan lists the series under "children's anime".
  • The Woobie:
    • Jyushimatsu falls into this pretty hard in "Jyushimatsu Falls in Love". The one time he actually falls in love with someone, and he gets rejected because she has to leave him. He's so heartbroken by this that he just breaks down in tears. Awww...
    • Karamatsu, especially after Season 1 Episode 5. It didn't help that supplementary material later revealed that he dislikes himself and uses his "cool guy" persona as a coping mechanism.
    • Choromatsu's usually comical grievances regarding his NEET lifestyle take a surprisingly sad turn in "Dayon Tribe", with Choro pretty much breaking down and admitting that he can't let go of his bad habits despite genuinely wanting to. It ends up making his successful progression in "Letter" all the more satisfying despite it not sticking.
    • It's not limited to the Matsunos either; Chibita had a lot of viewers feeling bad for him after what he had to go through in "The Life Of Chibita's Flower".
  • Woolseyism: The Viz English dub does its best to stay true to the spirit of the original while still appealing to Western audiences. Some replacements are a surprisingly good match for the original joke or reference.
    • In the original, when asked by his brothers what Totoko gave him to be her idol manager, he stammers his answer, making his brothers freak out—the first syllable in the sentence "She patted me on the back," is "se-", which sounds like "sex". In the dub, he mutters that it was "Just the tip"...of Totoko's finger, which is what she touched his arm with.
    • In "Iyami and Chibita's Rental Girlfriends", Iyami almost gives his disguise away with his Verbal Tic of adding "zansu" to the end of sentences—he covers by claiming he was talking about Zangief, from Street Fighter. Since Iyami loses the tic in the English dub, the reference relies on his Francophilia instead. He almost gives himself away by saying "bonjour," but covers by talking about Balrog (another Street Fighter character) instead.
    • In the Jyushimatsu special, Choromatsu tells Jyushi he's mixing up "yaoi" (BL manga) with "yakyuu" (baseball). The dub keeps the yaoi, but changes the second half to "Yay," as in "Yay, baseball."
    • In "Interview," Choromatsu's character asks Jyushimatsu what motivated him to apply—Jyushi mishears part of the question ("dokyo") as the sound effect for a heartbeat ("doki"), and mimes a painful heart attack. In English, Choro asks him about "a struggle" he's faced, which Jyushi interprets as "strangle".
    • In "The Karamatsu Incident," Jyushimatsu mishears Chibita's demands over the phone. First he mishears "kidnapped" (yuukai) as "yokai", thinking Karamatsu's been turned into a demon. Then he mishears "high tide" (manchou) and thinks Karamatsu's getting an enema (kanchou) in the ocean. In English, he mishears "ransom" (thinking someone said Karamatsu is handsome), then assumes "high tide" means Karamatsu is gonna overdose and die from getting high off of the ocean.
    • Ichimatsu's impression of Karamatsu was sprinkled with some Gratuitous English in the original dub, even mixing up the words for "outlet" (konsento) and "beauty contest" (kontesuto). For obvious reasons, the English version changes this to Ichimatsu just randomly telling objects how cool they are.

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