If you liked the Zoku Sayonara Zetsubou Sensei anime, the Anime-Planet community thinks you'd like:
Tatsuhiro Sato is a university dropout and a "hikikomori" – a person suffering from social withdrawal. To Sato’s dismay, his self-imposed exile from the world is rudely interrupted when a mysterious girl knocks on his door. She has charged herself with the task of curing Sato of his hikikimori ways! Now, as new problems ranging from hentai games to internet suicide spring up, can Sato manage to overcome his hermit-like ways, or will the imaginary N.H.K conspiracy force him to remain a hikikomori forever?
Zoku Sayonara Zetsubou Sensei is a comedy that takes people's neuroses, quirks and habits and caricatures them to the extreme, covering all sorts of areas such as suicide and society's ills. Another anime that explores very similar subject matter, albeit with a much more grounded and mature plot and drama, is Welcome to the NHK. If you're looking for a more serious anime (but which still has plenty of comedy), that tackles very personal subjects (while mocking/critiquing otaku culture as a bonus), I highly recommend the excellent Welcome to the NHK.
Watching ZSZS, I realised that it would be a very difficult show to make a recommendation for. The visuals hit you hard, the audio is slick and constantly changing, anfd you never feel like you comfortably settle into part of the show. I don't think any other show can reach the strange heights of ZSZS...
However, Welcome to the NHK does its damndest to keep up. Although not as disprate and visually bizarrel, it does have an eclectic mix of genres that will appeal to the otaku viewer.
Both shows are aimed specifically at people who know some of the nuances of the Japanese culture, and will keep you laughing along the way.
Both of these series focus on characters who are socially dysfunctional. If you liked that aspect of Zoku Sayonara Zetsubou Sensei, then you may also enjoy that about Welcome to the NHK. Also, even though NHK is generally more serious, both share a somewhat darker sense of humour.
Holding strictly to his family's creed, Kou Ichinomiya has never once, in his life of privilege, owed anything to anyone – that is, until a self-proclaimed Venusian named Nino saves him from drowning in the wake of a dire accident involving Kou's pants. Eternally indebted to the supposed extraterrestrial, Kou moves into her little community under the bridge along the Arakawa river. Ripped from his life of luxury and success, the young Tokyo U graduate now must adjust to his well-appointed hovel, strange new neighbors, and peculiar lover, Nino.
If you like a great cast of really random characters with a great ironic and dark type of humour check one out if you liked the other. Animation and music style are very similar as well along with quite wordy discussions.
As a huge fan of Zetsubou Sensei series, it was easy for me to get to the correct mindset for Arakawa. Both share such a similar humor and character design that they are almost the same. only the animation style differentiate them from one another. The main character in both even have the same voice actor.
Both animes are driven by the character caricatures that take one aspect of their persona and twist it into a running gag, but unlike Zetsubou Sensei, the characters in Arakawa are deeper than they would seem in the surface.
At Cromartie High, it’s tough being a delinquent -- a fact that do-gooder Takashi Kamiyama intimately understands. When he’s not engaging in contests of strength and rival gang wars, Kamiyama can also be found submitting punny jokes and planning his own rise to fame within the delinquents’ ranks, and that’s just the beginning! With friends like robotic Mechazawa, a giant gorilla, a hairy man from the 80s named Freddie and a clan of delinquents with mohawks that flow in the wind, how can anyone not enjoy high school?
Cromartie High School and Sayonara Zetsubou Sensei have similar kind of humour. Although Zetsubou sensei is in many ways more realistic and has more satire(there's some in cromartie too), they both share the variety of interesting and funny charachters.
In present-day Japan, Toshihiko Momota is member of a secret warrior faction called the Kifuuken. The Kifuuken is dedicated to destroying Shokujinji - humans that turn into man-eating monsters when hunger takes them. However, to fate's chagrin, Momota meets and quickly falls for Yuka, a Shokujinji herself! Will their love be able to overcome Yuka's insatiable appetite for human flesh, or will the couple be destroyed by the bestial tendencies of humanity?
I didn't greatly care for Zoku Zetsubou Sensei, but if you like unique art styles and weirdly spastic humour with a slice of dark undercurrent then it's just possible you'll enjoy Kemonozume.
In present day Japan, the life of a school girl is never dull. The easily-bored Konata never finds time to study because of her otaku habits, which frustrates hard-working Kagami to no end. On the other hand, laid-back Tsukasa always manages to go with the flow, while Miyuki is concerned with keeping her status as resident know-it-all. Join these four girls as they muse and meander their way through everyday events such as eating chocolate cones, doing homework, gaming, and trips to the beach galore.
Lucky Star and Zoku Sayonara Zetsubou Sensei are hilarious school-life comedies that often jeer at their target audience while entertainingly breaching the fourth wall. These shows achieve this outcome with a very well-defined cast of characters and unique art style. This style heartily supports the tone of both shows--Lucky, a saccharine, moe romp about four girls' seemingly uninteresting daily lives; Zoku, a more sarcastic and self-depreciating, yet equally upbeat view of a wacky high school class led by their manic depressive teacher.