I have already tried these, and if you to wish for something similar this is what I recommend:
Gintama
The Daily Lives of High school Boys
Cromartie High school
Handa-kun
Sakamoto desu ga
Gekkan Shoujo Nozaki-kun (Hilarious I died)
Kaguya-sama: Love is War
Baka to Test to Shoukanjuu
Ore no Nounai Sentakushi ga, Gakuen Love Comedy wo Zenryoku de Jama Shiteiru
KonoSuba
To Be Hero
Karakai Jouzu no Takagi-san
Masuda Kousuke Gekijou Gag Manga Biyori (I think this was funny but I can’t remember too well)
Kyou no 5 no 2
Lucky☆Star
Ben-To
Seitokai Yakuindomo
Seitokai no Ichizon
B-Gata H-kei
Haiyoru! Nyaruani: Remember My Love
Grand Blue (Really funny if memory serves correct and it was recent.)
Ore no Kanojo to Osananajimi ga Shuraba Sugiru
Yondemasu yo, Azazel-san.
Humanity Has Declined(Took forever to find this one but I’d definitely recommend this one. I just remember it being hilarious for some reason. The look of it is a complete contrast to what it’s actually about.)
Tsurezure Children(Would definitely recommend this for daily lives of high school boys. If my memory is correct that is.)
Beelzebub (I think this was pretty funny, can’t remember though.)
Katte ni Kaizou
Kore wa Zombie Desu ka?
Shinchou Yuusha: Kono Yuusha ga Ore Tueee Kuse ni Shinchou Sugiru
One Punch Man
Great Teacher Onizuka (I think it was pretty funny, memories are foggy as usual.)
In terms of novels I can only remember A Will Eternal off the top of my head.
Disclaimer: Most of these were seen when I was younger so my sense of comedy was probably different but I remember them being funny at that time.