If you liked
Katanagatari
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...then you might like
Densetsu no Yuusha no Densetsu
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Both shows share similar plot structure where the main characters gather legendary or mythical weapons forged by well renowned weapon artisans and have their treasures scattered in various different regions just to be claimed by their chosen ones. Though Legendary^2 Heroes tends to stray from the premise, Katanagatari remained in its goal though both of them have the similar open-ended conclusion but indifferent proposition about their world's present time.
If you liked
Sayonara Zetsubou Sensei
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...then you might like
Kuuchuu Buranko
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Black humor oriented shows that usually deal with medical psychology in both internal and external factors, they only differ in settings but has the same episodic routine. They also both eccentric art style and witty figurative symbolism, though SZS relies more on parodies and reference KB does it less.
If you liked
Gintama
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...then you might like
Tonari no Seki-kun
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Do you like Katsuras dreams and delusions like where a simple count of leap of a sheep in mind he had to fall asleep, turns into a heartwrenching storytelling of a young ladys leap of faith. Well, if you enjoy insane troll logic for fun you might like to watch Tonari no Seki-kun, though the whole show is a running gag in a skit format.
If you liked
Seitokai Yakuindomo
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...then you might like
Mangaka-san to Assistant-san to The Animation
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Both are comedy harems with cliche set of plot and archetypes, character interactions usually leads to off-color humor. They're also both in skit while SYD uses is more focus on slapstick, MTATTA uses a variety of meta-humor and comedic analogies. The manzai roles are also reversed between the series.
If you liked
Fate/Zero
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...then you might like
Nobunaga the Fool
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If you enjoy watching characters that are based on historical figures then you might like to watch both, also, yeah... there's a coffee in the Holy Grail. NTF is pretty much like F/Z just with mechas. It also had some predictable flat plot flag lines in the series.
If you liked
Dakara Boku wa, H ga Dekinai.
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...then you might like
Kenzen Robo Daimidaler
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Blue pill can be expensive sometimes, just grab a blue comedy anime as a stimulant. Will only cost you some brain cells, effects aren't 100% assured.
If you liked
Yakitate!! Japan
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...then you might like
Jinrui wa Suitai Shimashita
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Bread Science, Black Humor, Political satire and Time travel put in a comedic medium.
If you liked
Ginga Eiyuu Densetsu
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...then you might like
Mahou Shoujo Madoka★Magica Movie 3: Hangyaku no Monogatari
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Both story surrounds dictatorship, democracy and utilitarianism inside an endless spiral of cosmic illusions. Both shows would make a good shampoo commercial.
If you liked
Level E
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...then you might like
Kotoura-san
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If you're the type of person who is looking for a good trolling author experience then I suggest both series. Though they may differ in theme and humor they are cleverly written to trick the audience expectations of narrowed expected events.
If you liked
Ixion Saga DT
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...then you might like
D-Frag!
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Both may have different character setup but both of it is anti-generic (or pretty much poking with tropes), they both do have the same level of creativity on observational comedy and usage of spontaneous humor about gaming, though Ixion Saga have redundant Blue comedy (traps) in it while D-Frag doesn't use it much.
If you liked
Rekka no Honoo
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...then you might like
Mahou Shoujo Madoka★Magica
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It's trivial but if you want the to the naming reference between some characters then you might like to watch both series, whereas Sayaka represents the blade, Homura represents the snake(probably Ouroboros, ergo time-travel) and Madoka the tortoise(could represent as spatial imprisonment, the barrier and her slow development). It also share the same equation from the anagram emotion substituted to ((E)+(motion)) that could represent the sum of heat energy & kinetic energy and the way it was conserved to prolong Enthalpy and slow Entropy(I'm kidding, but it would make sense) which where the plot also revolves.
If you liked
Monster
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...then you might like
Jormungand: Perfect Order
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"I'll be here sitting on my couch with my bud, eating popcorn while watching every man in this world kill each other" Casper Hekmatyar & Johan Liebert But on a serious note though if you like shows with characters that has counter-idealistic human nature you should try one or the other.
If you liked
Gintama
|
...then you might like
Hoozuki no Reitetsu
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I guess another derivative have spawn from hell. You got both main character that has versatility to do different task and some stuff for jokes and laughs. Though Hoozoki no Reitetsu is like Dante's Divine Comedy that elaborates pessimistic virtues in hell while Gintama that has more variety and spices in its series that displays mostly realism.
If you liked
Yondemasu yo, Azazel-san. (TV)
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...then you might like
Hoozuki no Reitetsu
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You'll probably know more about different types of hell. Eastern and Western compared stereo-typically.
If you liked
Tentai Senshi Sunred
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...then you might like
Naruto SD: Rock Lee no Seishun Full-Power Ninden
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Uses the known medias of archetype shounen tropes and turning them into parody for entertainment purposes attributing more possible elements of comedies, though Rock Lees own sitcom is reliant to the Naruto series itself (since its where their character techniques and world is introduced) though it only focuses on laughter and not making sense while Sunred have an arms of their own without going off in its comparison which is Power Rangers.
If you liked
Yahari Ore no Seishun Love Comedy wa Machigatteiru.
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...then you might like
Watashi ga Motenai no wa Dou Kangaetemo Omaera ga Warui!
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Series that are being anti-genre towards rom-com and have their witty (mostly sarcastic) dialogues as arsenal on their series. Both main characters have introvert personality that has a lot of internal monologue throughout the series which usually has a slapstick on its end although SNAFU has much pessimistic dark humor (which more entertaining to mature audiences) than Watamote. Most of its dissimilarities is their character setup, though Hikigaya might be Kurokis male comparison he doesn't have a bad habit on succumbing himself on playing games but have his experience on real lady friends from her past, He is also more tolerant on his societal dysfunction or pretty much he just hates having friends, closest relationship would be acquaintance, also SNAFU doesn't circle much on the Male lead alone while Watamote is only focused on Kurokis daily life adventure.
If you liked
Jinrui wa Suitai Shimashita
|
...then you might like
Yahari Ore no Seishun Love Comedy wa Machigatteiru.
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Both series have more or less have the same content that exploits human natures tendency to collapse due to corruption, misinformation, immaturity, ignorance & forced societal complementary.Self monologues are the highlight of both series though that would be obvious since the characters have introvert sides, also had a slow start due to foreshadowing, it also had four seasons without winter. Only difference is that SNAFU is more straightforward and doesn't like to present things in a metaphorical analogies unlike JWSS does most of the time, it inputs real somewhat humane characters instead.
If you liked
Gintama
|
...then you might like
Angel Beats!
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Both uses the combination of sociopathic comedy and anti-comedy as an entertainment. Character dramatization are backstory reliant though tearjerking in sometime. The OST of both series are almost the same. Only difference is the themes and art-style, moe & anti-moe.
If you liked
Suzumiya Haruhi no Yuuutsu
|
...then you might like
Hataraku Maou-sama!
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Bizarre comedy that relies with non human character standpoint indifference, only difference is that Haruhi setting is about school while other Maou is to restaurant, Main Protagonist is unaware of their own eccentricity to other people and their normal environment to make a slapstick.
If you liked
Shinseiki Evangelion
|
...then you might like
Toushou Daimos
|
Mecha genres with similar pain transceiver that sends pulse signal to the pilot, both of them have symbolism about heaven and reliant in battling the extraterrestrial in order for the story to progress, only thing is that Daimos is a bit similar to Shakespeare Romeo and Juliet and focused on Drama and Romance, while NGEs resolution is about a certain project in order for humans consciousness to progress.
If you liked
Death Note
|
...then you might like
Psycho-Pass
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The series have the same showcase of "Law versus Crime", the only difference is the themes. In terms of characters Death Note revolves around two Genius students with different personality and the anti-hero holding a handy-dandy Reaper Notebook while Psycho-Pass revolves between Cops using Advance Techno weapon that has full duplex psychological inspection that switches the gear from a Neurological paralyze r to Anti-matter shooting bullet and Masterminds that have odd different assassination fetish.
If you liked
Gintama
|
...then you might like
Medaka Box
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Similarities: Sarcastic, Nihilistic Philosophies for humorous purposes, Parodies that breaks the 4th wall, High detailed animation during action scenes, Some costumers are usually a plot device to the story. Differences: Themes, settings and fanservice.
If you liked
Gintama
|
...then you might like
SKET Dance
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Similarities: Sarcastic, Parodies that breaks the 4th wall, High detailed animation. Some costumers are usually a plot device to the story. Differences: Themes (School & Feudal Japan), settings. More drama no or less action.