If you liked
Azumanga Daiou The Animation
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...then you might like
Alien 9
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Both take place in a school setting and have similar character art. Both have bizarre situations based on the sci-fi elements in Alien Nine and the overall comedic elements in Azumanga Daioh. If you like the weirdness in either one, you should watch the other.
If you liked
Kyougoku Natsuhiko: Kousetsu Hyaku Monogatari
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...then you might like
Inaka Isha
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Both have a very distinctive, bizarre art style and share a similar atmosphere although I would say Inaka Isha is a bit more bizarre than Hundred Stories.
If you liked
Black Cat
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...then you might like
Tegamibachi
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Train and Eve from Black Cat automatically reminded me of Lag and Niche from Tegami Bachi. Just like Lag and Niche, Train and Eve travel together (along with an extra companion who is the comedy relief character - same as Tegami Bachi). Lag and Train are both gun-wielders, but Train originally used his gun for assassination while Lag uses his gun to uncover feelings left behind in objects. Niche and Eve are both young females who are powerful weapons, but they eventually join Lag and Train respectively on their journeys. Besides those characters, both shows have specific organizations that carry out duties: Tegami Bachi delivers letters and Chronos is concerned with supposedly making the world a better place. Interestingly enough, Lag starts out wanting to join Tegami Bachi and eventually joins while Train starts out as the Black Cat in Chronos, but leaves the organization later on.
If you liked
Full Metal Panic? Fumoffu
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...then you might like
Hayate no Gotoku!
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Both are romantic comedies with a loud-mouth girl and her dense bodyguard as the main characters. Either one or both shows are guaranteed to make you laugh.
If you liked
Bokusatsu Tenshi Dokuro-chan
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...then you might like
Hayate no Gotoku!
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Hayate is a parody of other anime and Dokuro-chan is somewhat like a parody itself. They are both considered "hilarious" but it depends on your sense of humor. Just be aware Dokuro-chan is the more raunchy version of the two.
If you liked
Cardcaptor Sakura
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...then you might like
Kaleido Star
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You'll notice the similarities of two particular characters: Sakura and Meiling from CCS and Sora and May from KS. Both Sakura and Sora have this great aura of optimism and determination that seems to change people around them. As a result, Meiling and May, who come off as annoying, loud-mouth girls who provide the humor in the shows, cannot be completely hated even though you really want to hate them because no matter how they act towards Sakura and Sora respectively, they are the type of characters who cannot bear a grudge. Not to mention, both Sakura and Sora are Japanese while Meiling and May are Chinese.