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If you liked Cowboy Bebop add

...then you might like Akudama Drive add

gritty urban sci-fi settings, ensemble casts with checkered histories, complex heists/fetch quests, dystopic lore implications, hacker characters, jaw-dropping action scenes that usually result in a large structure exploding into rubble, unhinged ladies, child endangerment- what more could you ask for? cd projekt red devs will cry, throw up and quake in their boots just thinking about how flawlessly these two shows exemplify the cyberpunk aesthetic and it's core themes.

If you liked Himouto! Umaru-chan add

...then you might like Aho Girl add

sol comedy in which a goofy strawberry blonde girl pesters a grumpy black-haired boy. aho girl's jokes are dirtier and less referential, but it's structurally similar and tonally identical to umaru overall. each have side characters that fit into the obsessive stalker/yandere archetype (fuuki and kirie) and mild mannered best friend archetype (sayaka and ebina). aho-girl lacks the variation in conflict that umaru's dual persona provides, but if you like this particular style of overexaggerated humor, both will scratch that itch.

If you liked Full Metal Panic? Fumoffu add

...then you might like Gintama add

similar sense of humor/general vibe, and the male protags are reminiscent of each other. both shows include absurdist subversions of japan's costumed mascot phenomenon, as well as what i'd refer to as a "hybrid" setup, where the base plot is essentially a combination of two common anime settings (school + military in fumoffu, ancient japan + sci-fi in gintama). released around the same time so they have practically the same animation style. more of a rec for fumoffu -> gintama since the latter is much longer and higher quality.

If you liked Toaru Kagaku no Railgun add

...then you might like Lycoris Recoil add

both main casts are part of a covert law enforcement organization comprised almost entirely of schoolgirls trained to neutralize domestic terror events. if i had a penny for how many times this has been an anime premise, i'd have 2 pennies, which isn't a lot but its weird that it happened twice. also has romantic tension between two of the females leads and a slow-burn mystery in common. lycoris is better imo

If you liked Medaka Box add

...then you might like Kaguya-sama wa Kokurasetai: Tensai-tachi no Renai Zunousen add

student council makes up the main cast, over-the-top presentation of ordinary school scenarios and strongly developed characters. medaka box focuses less on mind games and misunderstandings, and more on solving oddly specific conflicts episode-to-episode. both are similar in tone, setting and sense of humor, but they most notably share a bittersweet but ultimately compassionate outlook on life.

If you liked Sen to Chihiro no Kamikakushi add

...then you might like Jibaku Shounen Hanako-kun add

both incorporate lowkey eldritch supernatural elements and lots of crazy lookin yokai into the real world. also have similar protagonists and beautiful art direction, but hanako focuses more on worldbuilding development and overarching plots as opposed to spirited away's more nonsensical nature.