 If you liked
Saiki Kusuo no Ψ-nan
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 ...then you might like
Uramichi Oniisan
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i would say if you really enjoy the comedy of one of these anime, then you will definitely enjoy the other one as well
they have the same kinda vibe to the main characters (uramichi and saiki)- very tired and annoyed from everything and everyone around
Cynical, stoic, tired of life MC in a bubbly environment dealing with stupid, silly, lovable side characters with some cute moments of softness and sentimentality sprinkled in that will make u feel all warm and fuzzy inside. Also both fun, funny and silly :3
Cynical stoic main character in a bubbly environment dealing with young optimistic children while facing a midlife crisis. All the other characters have their own schticks that add to the comedy of this anime. I feel like if you liked Saiki K, you'd enjoy this.
Both feel sort of similar in a way. I definitely think that if you enjoyed the humour in Saiki K that there is a good change you will enjoy what Uramichi Oniisan, even though the latter show has a slightly more realistic slice of life view of things.
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Recommended by bananasaur590
The main characters, comedy, color pallets, and cast of characters are very similar. Even though the comedy from each show are mostly different, they both have the same vibe. I think anyone who enjoys Uramichi-Oniisan will find Saiki K just as or even more enjoying.
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Recommended by Ace_0f__Spades
both shows have episodes that are short compilations of events/stories. You still feel a progression in story but fast paces while funny.
I think the comedy in both shows gives off the same vibe, despite being in completely different settings. The main characters are similar. If you liked the humor in Saiki, I'm sure you will like the humor in uramichi oniisan as well.
At first glance, these two series don't seem to have much in common, other than being comedies. So why am I recommending them? Simple: Hiroshi Kamiya. He voices both Saiki and Uramichi, and both characters have a very similar vibe of being completely done and fed up with their lives. If you enjoyed that aspect of Uramichi Oniisan, you may very well enjoy Saiki K. - or vice versa.
main characters who seem indifferent and tired of life with amazing comedy, also both mcs voiced by same va hiroshi kamiya
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Recommended by fushieternity
Comedy, Uramichi Oniisan could be considered more "adult" humor at some points.
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Recommended by breadhurts
main character is a little similar to Saiki
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Recommended by Justine0180
Both anime have fast-paced, offbeat humour, with a vibrant cast of characters. Saiki and Uramichi Oniisan have a similar deadpan outlook on life, with moments of softness and sentimentality that make them as likeable as they are. There's also a lot of pun-based humour if you know where to look, especially in the names of both casts of characters. Anyone who enjoys one of these anime will definitely enjoy the other!
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Recommended by sleeplessandst2
an apathetic and dead inside protag with a cast of loud and annoying (affectionate) characters. very silly.
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Recommended by Pathoswashere