 If you liked
Sayonara Zetsubou Sensei
|
 ...then you might like
Uramichi Oniisan
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Both feature leads working with kids and both are pretty pessmistic and both focus around comedy plots as well too.
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Recommended by Disapeared_Ghost
Same voice actor for MC who is depressed, subservient and very analytical. Very adult dark comedy about work, unfulfillment and life in general. I had to check several times if Uramichi Oniisan author wasn't also Kōji Kumeta because humor is very similar.
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Recommended by blackhaulmike
Life sucks hard and really is a pain in the ass when you become an adult. Both anime talk about the realities of modern society and deal with people with constant depression ... while still being hilarious.
Uramichi and Nozomu share most of their personality traits about being in despair, and are also voiced by the same voice actor, which is coincidentally ironic and funny.
Both are dark comedies. While SZS is more wacky, bizarre and has a ton of Japanese culture/folklore references, Uramichi Oniisan is very straightforward. The social commentary and humour are very similar, and the characters in both the series are named in ways that define their personalities. A fan of either is likely to appreciate the other.
Black comedy with depressed main character who works with kids, teaches them important life lessons (for example, that some things in the modern society are stupid), whose name has not very happy meaning ("Despair" for Itoshiki if his name is spelled horizontal and its kanji are too close to each other, and "Depressing" for Uramichi).
Also, both anime have very little respect for the fourth wall.