Sayonara Zetsubou Sensei
Sayonara, Zetsubou-Sensei

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Both stories - comic manga about new teachers who teach their problematic students more real life than school subjects.  

Both are hilarious comedies around a strange teacher and very interesting characters as students. The two have truly awful artwork so keep away if it matters for you. 

Both of these titles revolve around eccentric characters whom all possess at least one abnormal and distinctive personality trait. 

Given that they were written by the same mangaka, there are several similarities between these two works. The most prevailing similarity is how the protagonists wear particular lenses that determine their perception of life and everything around them. In Katteni Kaizou, Kaizou believes everything is associated with an alien scheme to take over the world. In Sayonara Zetsubou Sensei, Itoshiki views everything in a negative manner. Both very funny and random. 

Both of these are comedies with suicidal protagonist, and even contain the same "What if I had died?" punchline, though SZS has overal more sophisticated jokes. 

Satirical comedies with a dark sense of humor. Both also have similar chapters dedicated to parodying Matthew C. Perry. 

If you enjoy comedies build around a pessimistic, suicidal protagonists, then this might be to your liking. 

Both of these works are satirical take on usual harem routines. If you enjoy black humor, you might like these. 

Both are similar in having a teacher that guides it's class in weird ways that ends up being great for comedic effect, with the one difference that szs goes in a path that allows it to explore much more what it's trying to do and allow for funnier gags (I'd also probably recommend great teacher onizuka as well but since i haven't seen or read it yet i won't say much about it, but i think it's also worth giving a try as well) 

Similar minimalistic artstyles, similar references literature, same strange sense of humor 

Zetsubou sensei is also a comedy manga with a dark tone to it. The art style used in this manga is quite similar to Koji Kumeta-sensei's work, so much so that I had to confirm whether the artist was in fact a former assistant of his or something. SZS has more reference-related gags as compared to Voynich hotel. 

Now, I know what you're thinking. These two mangas couldn't be farther apart, and I would agree with that up to a certain point. Where I draw the similarity here is how they both felt. Both of these mangas feel very similar to one another especially in terms of the humor. In both manga every chapter is some new non-sensical tangent on a completely random topic, In Utakata Dialog this humor is conveyed through puns and the witty comebacks of the pair, In Zetsubou Sensei this humor is conveyed through big displays and odd but interesting examples. In both, the humor is fast-paced but highly enjoyable. If you enjoyed the humor in Utakata Dialog, then you will enjoy the humor in Zetsubou Sensei. TLDR: Both have the same non-sensical fast-paced type of humor. read more 

Atypical harem manga about a protagonist that is surrounded by weird girls with abnormal quirks. 

Zetsubou Sensei is this manga's polar opposite. Where this manga is surprisingly wholesome, SZS is dark and cynical. Where these are both similar is the top notch comedic writing, and use of referential humor. Both manga have literally gotten me to laugh at their gags out loud.  

Dialogue/monologue heavy comedies with a charismatic lead and plethora of references, allusions and social commentareis in humorous form. 

Sayonara Zetsubou-sensei and Welcome to the NHK are timely satires. Both series also focus on pessimism and despair, as exemplified by Satou's being a hikikomori, adult-game developer and Nozomu's being a suicidal teacher. 

Even though the authors are different, these manga are both set at school, and have the same type of comedy and parody elements. While in SZS we have a male lead surrounded by girls, in MH we have a female lead surrounded by... girls. And a trap. Both manga also got a great anime adaptation by SHAFT. 

These manga are both great examples of Japanese black humor. While SZS takes aim at a wide swath of contemporary Japanese society, Super Cruel focuses on the specific world of manga-ka. Both have a style of humor that can be vicious or vulgar (especially in Super Cruel), but if you enjoyed one of these, the other is definitely worth a look. 

In these two publications, what the audience is subjected to is how things can be approached in negatively dramatic ways. However, this is the only similarity between these two series as one is geared for comedy and the other for drama. 

Both are hilarious and have no continuing plot, but episodic chapters. Though SZS is darker in tone and Gintama is sillier, both consist great satire. 

New teacher gets a class that is full of weirdos and has to deal with them. The girls proceed to fall in love with said teacher. While Sayonara Zetsubou Sensei is a satire, Negima plays the harem tropes straight. 

Do you like dark suicidal humor? If that is the case consider picking up those two titles. 

The main characters of both series are REALLY negative (although in different ways). They both also know a girl who is REALLY positive. En Passant isn't a very well know series but it's really promising. If you like Sayonara Zetsubou Sensei you should give it a try. 

Black humor satire with creative jokes. Difference is that while SZS is mainly tied to dialogue, Dance! Kremlin Palace has plenty of visual jokes, frequently explicit. 

(This recommendation is specifically for the Ekimae Ankoku one-shot, but works for the whole Ana Moji anthology too) Both are satirical works that take a concept and create a sort of "rant" abut it that takes it to an absurd degree as a way to criticize some part of society.