Gekkan Shoujo Nozaki-kun, Saiki Kusuo no Ψ-nan Recommendations
In a certain sense, Saiki can be considered as the "male" version of Gekkan Shoujo Nozaki-kun, since while Nozaki parodies the shoujo's tropes, setting and characters, Saiki does the same, only with works for the shonen audience. The only difference is that Nozaki is strongly focused on romance and sometimes are sentimental, while Saiki always remains a gag comedy with an unceasing parody and humor.
While Saiki Kusuo is parodying Shonen tropes, Gekkan Shoujo is parodying shoujo tropes.
Both have a similar type of humour, a collection of random story in one episode, and the characters are really unique.
The comparison between characters is like this
Saiki -> Nozaki
Teruhashi -> Chiyo
Mikoshiba -> Kaidou
I highly recommended both anime since it will make you laugh out loud alone in your quite room
High school anime paroding stereotypical characters and their relationships.
What else can I say.. The type of humor, the lenght of episodes (or "sketches"), typical "highschool" situations, unrequited love... If you were falling off your chair with laughter because of one, the same will probably happen with the other.
You need some experience of-fu watching cliche anime to enjoy these shows to the fullest. Plus both main characters are immune to falling in love. Nice comedies.