Osomatsu-san is the definition of chaotic comedy—absurd, unpredictable, and endlessly self-aware. At the heart of its hilarity are the Matsuno brothers: six identical ne’er-do-wells with wildly different personalities and a knack for turning even the most mundane situations into full-blown disasters. From breaking the fourth wall to pulling off the most ridiculous skits in anime history, these are the moments that left us wheezing, crying, and wondering how six brothers can be this unhinged.
#10: The “Job Interview” Sketch (Season 1, Episode 3)
In this iconic segment, the brothers attend job interviews—and instantly turn them into trainwrecks. Whether it’s Karamatsu being unbearably cringe, Ichimatsu glowering silently, or Choromatsu trying way too hard to be the “normal” one, each interview descends into a new level of awkwardness. What’s brilliant about this sketch is how it satirizes not just the brothers’ personalities but real-world job interview pressure. The interviewer is constantly exasperated, and by the end, you feel sorrier for him than for the NEETs. The comedic timing, rapid shifts in tone, and absolute lack of self-awareness from the brothers make this a classic Osomatsu-san moment. It’s the perfect intro to just how dysfunctional this family is—and why we love them for it.
#9: The Idol Auditions Parody (Season 1, Episode 9)
When the Matsuno brothers audition to become idols, they unleash one of the show’s most self-deprecating and bizarre parodies. Dressed in ridiculous outfits and spouting nonsense, they each bring their version of “idol charm”—which ranges from pitiful to downright disturbing. Osomatsu tries to be cool but flops. Todomatsu turns on fake cuteness. Jyushimatsu… unhinges reality. The episode spoofs real idol culture with absurd flair, mocking how far some characters will go to be “marketable.” The blend of satire, weird poses, awkward dancing, and fanservice (of the most cursed kind) makes this sketch legendary. It’s a meta moment that celebrates and roasts anime tropes in equal measure, proving the series isn’t afraid to dunk on itself for a laugh.
#8: The Brothers Become Girls (Season 1, Episode 18)
In this gender-bending episode, the brothers wake up as girls—and the results are predictably chaotic. Each “sister” perfectly matches their original personality but brings a new level of energy to the episode. Choromatsu becomes a sensible big sister. Karamatsu becomes a painfully dramatic diva. And Jyushimatsu? Still Jyushimatsu, but now in pigtails and destroying physics. What makes this moment so funny isn’t just the premise—it’s how committed the show is to the bit. The animation shifts into “pretty girl anime” mode, but the core absurdity remains. The episode manages to be both a loving parody and an unhinged comedy sketch. It’s also surprisingly thoughtful, proving Osomatsu-san can go wild without losing its character-driven humor.
#7: The Baseball Episode – Jyushimatsu Goes Full Chaos (Season 1, Episode 7)
The baseball episode centers around Jyushimatsu—the wildcard of the family—and his journey to join a local team. Except… he’s not playing baseball. He’s playing Jyushimatsu-ball, a sport that includes swimming across bases, bouncing off light poles, and using the bat like a helicopter. The episode plays with classic sports anime tropes and completely breaks them. There’s over-the-top drama, intense training montages, and heartfelt speeches that get drowned out by total nonsense. Jyushimatsu’s pure-hearted madness, combined with the straight-faced reactions of his teammates, make this one of the show’s most endearing and hysterical episodes. It’s the perfect example of how Osomatsu-san uses genre parody to fuel its comedy.
#6: The Zombie Apocalypse Sketch (Season 2, Episode 2)
Leave it to the Matsuno brothers to ruin a zombie apocalypse. When the undead begin attacking, instead of fighting or fleeing, the brothers argue over who gets to be the protagonist. They fight over camera angles. They fight over “main character” lines. Meanwhile, the actual zombies just… watch in confused silence. This moment is comedy gold because it flips the zombie genre on its head. There’s no survival instinct—just ego, delusion, and utter chaos. Choromatsu tries to be the hero. Karamatsu monologues with sunglasses. Jyushimatsu becomes a zombie voluntarily. It’s the kind of irreverent sketch that shows why Osomatsu-san thrives in the absurd. The world is ending, and the brothers are still bickering about screen time.
#5: Osomatsu and Karamatsu’s Double Date Disaster (Season 2, Episode 10)
When Osomatsu and Karamatsu somehow land a double date, the audience is instantly skeptical—and rightly so. What follows is a cringeworthy, laugh-out-loud unraveling of everything that can go wrong when two overconfident, clueless men try to impress girls. Osomatsu tries to act smooth but ends up being a lazy slob. Karamatsu, in full “cool guy” mode, brings out the leather, the sunglasses, and the painful one-liners. Their complete lack of self-awareness makes the dates unbearably awkward. The girls are unimpressed. The waiter is terrified. The audience is wheezing. This sketch is peak character comedy—showing just how far the brothers are from functioning adults, and how even a simple dinner can devolve into disaster when the Matsunos are involved. It’s like watching a slow-motion trainwreck made entirely out of comedy.
#4: The Self-Awareness Episode – Matsunos Watch Their Own Show (Season 3, Episode 6)
In one of the most meta episodes ever produced in anime, the Matsuno brothers sit down to watch an episode of Osomatsu-san. What follows is a breakdown of the fourth wall so complete, it becomes performance art. The brothers criticize the animation. They argue about which of them is getting the most screen time. They complain about the writing, the jokes, and even the voice acting (which, yes, is all the same cast). Watching fictional characters review their own show—while roasting each other and the production team—is next-level absurdity. What makes this episode hilarious is how unfiltered and chaotic it becomes. No one is safe from mockery—not even the fans. It’s comedy so self-referential, it feels illegal. And that’s exactly why it works.
#3: Iyami’s “Sheeeh!” Comes Back in Style (Various Episodes)
Though not one of the brothers, Iyami’s recurring gag of yelling “Sheeeh!” while contorting his body into bizarre poses is legendary—and every time the brothers get caught up in it, chaos erupts. In one unforgettable sketch, the brothers try to out- “Sheeeh!” each other in public, turning a simple gag into a slapstick explosion of ego, pride, and increasingly stupid poses. Whether it’s on the street, in restaurants, or during serious conversations, the moment someone screams “Sheeeh!” the energy instantly turns to madness. What makes it so funny is how seriously they take something so ridiculous. It’s the kind of classic gag that never gets old, especially because Osomatsu-san leans into it way too hard—intentionally.
#2: The “Osomatsu Casino” Sketch (Season 2, Episode 1)
In a full parody of gambling tropes and casino drama, the Matsuno brothers find themselves at a cursed casino where the odds are never in their favor—and yet they keep playing. Osomatsu tries to play it cool. Todomatsu thinks he’s gaming the system. Ichimatsu just sulks. And then the ultimate twist: Jyushimatsu starts winning everything, but only by defying every law of probability and sanity. The absurdity builds until it peaks in a whirlpool of flashing lights, failed dreams, and screaming. The sketch perfectly spoofs high-stakes gambling anime like Kaiji while still being rooted in Osomatsu-san’s signature nonsense. The way the brothers collapse into debt, betrayal, and disbelief—only to do it all over again—is the purest form of dumb, delightful humor.
#1: “Totty’s Popularity Scheme” (Season 1, Episode 17)
Todomatsu (Totty), the youngest brother and self-proclaimed “normal” one, concocts a plan to become more popular with girls. The scheme? Create distance from his brothers and craft a “cooler” image. What follows is a rollercoaster of desperate lies, over-the-top fake personas, and every kind of social media post you can imagine. Of course, the rest of the brothers find out—and ruin everything. They show up at his hangouts. They expose his fake hobbies. They cheerfully burn his “cool guy” facade to the ground. Watching Totty go from smug to panicked as his brothers out him in front of real people is one of the most hysterical things Osomatsu-san has ever done. The timing, the voice acting, and the slow realization that he can never escape their collective chaos makes this the perfect blend of sibling comedy and total comedic anarchy.
The Matsuno brothers of Osomatsu-san are a never-ending source of ridiculous, unpredictable hilarity. Their best comedic moments come not from elaborate setups, but from their interactions—their dysfunction, their delusions, and their total lack of shame. Whether they’re breaking the fourth wall, bombing a job interview, or ruining each other’s lives for fun, the Matsunos prove that even six grown NEETs can deliver some of the sharpest, most absurd comedy in anime. These ten scenes remind us that sometimes the most glorious kind of chaos comes from a family that shouldn’t work—but somehow, hilariously, does.
