If you're looking for anime similar to Wooser no Sono Higurashi, you might like these titles.
All Asakura wants is to graduate and become a high school teacher, but not for the reasons you’d expect: he wants to be surrounded by boobs - ample, bountiful boobs. But Asakura’s goal of mammary immersion won’t come easy, as his best friend Ishida is determined to open a flower shop with him once they graduate - that is, if they manage to graduate. Together, the duo navigates day-to-day school life with crass, whether they’re ogling their busty teacher, taking on part time jobs or dodging assassination attempts by robots.
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Both of these short anime have slow, dry humor. Ishida is by far the better of the two because it is actually entertaining!
Miss Monochrome, an idol who lives in a luxurious castle with her trusty Roomba companion, wants nothing more than to be back in the spotlight like the popular idol Kikuko. But the road to stardom will be fraught with challenges, from finding a trustworthy manager, to getting bit parts on TV, to even getting the media to notice her glorious talents and amazing feats!
Both are Sanzigen shows. Both are a few minutes long. And both are hilarious. Wooser even pops up in her show and vice-versa. You like one, you'll like the other.
One day, without warning, a huge hole appeared in the world and demons emerged, ready for battle. Assuming that the demon king sealed by a hero 1,000 years ago must have escaped, the king of the land set forth a decree: the hero’s descendents must defeat evil once more! For Alba, one such would-be hero, this journey will be anything but ordinary given his growing collection of bizarre and wacky companions. Alongside young demon Ruki, age-inappropriate Ruldolf, tentacle-fighter witch Zwei and a host of others, Alba will get arrested, play dodgeball, travel across the land, and least importantly, learn the truth about the hole in the world!
Wooser and Senyuu combine the format of very short episodes with comedy that is at first glance innocent enough but proves to be rather more self-aware. The level of snark is right about the same and they even use humorous narration for parody purposes.
The "Nyanbo" are creatures with square bodies with ears and tails that came to Earth from outer space. There's Tora, who dreams of repairing their broken UFO and returning to space, as well as his sister Kotora, the precocious Shiro, the mischievous Mike, the mysterious Kuro, and many more. All of these Nyanbos are now happily living much like cats, free-spirited and sometimes getting into trouble, in places that humans don't know about.
It follows the daily life of Kotetsu-kun, who aspires to be an astronaut, and friends at the Animal Space Academy as they all pursue their dreams.