 If you liked
Azumanga Daiou The Animation
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 ...then you might like
Shinryaku! Ika Musume
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If you like nonsense comedy, go with Shinryaku! Ika Musume and Azumanga Daioh. The first is some kind of an amateur version of the second, but the laughter is guaranteed either way.
And don't forget: Osaka-san rules all!
Episodic comedies with great characters and similar senses of humor. They are both quite touching at times and downright hilarious at others.
With both shows each episode has some shorts that all seem to connect. Both shows are cute and funny.
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Recommended by hamstar138
Both shows are slice-of-life anime that seem fairly mundane at first (even if you consider Ikamusume a fantastic creature), but are very surreal underneath. Both series also feature loveable characters that seem natural and unique.
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Recommended by Solarius_Scorch
Similar comedic style; lots of randomly-themed, upbeat humor. The characters are also delightfully similar.
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Recommended by Valkyrie_Wings
If you like one series for the characters who create great light-hearted comedy through sheer force of their colourful personalities, you would probably like the other too.
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Recommended by TotalPotato
These series share a common structure, in which each episode is divided into a series of sketches that revolve around a set theme. Additionally, characters possess similar traits and an offbeat sense of humor is present throughout the entire show. Very fun and amusing.
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Recommended by MarisaTheCube
Shinryaku! Ika Musume and Azumanga Daioh both follow a group of friends going through their day to day life with pretty hilarious and funny moments. The group dynamics of both friend groups in both Shinryaku! Ika Musume and Azumanga Daioh make those two anime definitely worth watching