 If you liked
Sayonara Zetsubou Sensei
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 ...then you might like
Maria†Holic
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similar style and humor. and both main characters are in "despair".
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Recommended by yarvenclog
Both series are comedies done by SHAFT in similar styles. While Maria Holic has a more structured plot, it can be just as wacky as SZS. Maria Holic also parodies Nozomu's despair sequence from time to time, which SZS fans will love. I suspect that Dorm Mistress and Kafuka are related. They are eerily similar.
Both anime are awesomly done by SHAFT, and also share some voice actors.
Both are comedies with the parody element and a black sense of humour.
Both main characters are in despair.
Both are set at school and have a good, interesting cast of characters.
Both have shoujo-ai, even if in SZS they're only hints.
Both are worth watching, but Zetsubou Sensei is better.
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Recommended by RenaPsychoKiller
Both are Studio SHAFT productions under the helm of Akiyuki Shinbo, which rely on fast paced gags, puns, and innuendos.
The style of comedy is similar, and some of the jokes cross over from Zetsubou-Sensei
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Recommended by gloomheart
Both series have the same producers so there are elements which are similar between the two. The comedy and the art style are basically similar.
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Recommended by MiraelWhite
It's been said and exhausted before, but both are fun, crack, series to watch when you're in the mood for a great comedy. Both Sayonara Zetsubou Sensei and Maria Holic do not have much continuity (Maria Holic has a slight bit more, but that's not saying much), great opening themes, and a great sense of humour.
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Recommended by Yandere-chan
Beyond the obviousness of their both being Shaft productions, each has a single theme that gets beaten senseless. These one-trick ponies get lost in the wilderness and well before they actually finish, each runs out of things to say. Many episodes would have benefitted from losing 5-10 minutes since much of the repetition would have been cut. Losing a few episodes would have helped the series as there were a few too many in which nothing happened -- the season finales offending most egregiously.
Typical for Shaft shows, the music is mostly interesting. The artwork is good and the characters are visually attractive.
To sum the experience
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The artwork and the animation is pretty much the same. Maria Holic might be a little lighter than Sayonara Zetsubou Sensei, but there's numerous characters and lots of high school girls absurdities in both of them.
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Recommended by cockroaches