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If you liked Cowboy Bebop add

...then you might like Samurai Champloo add

Both include heavy themes as well as leaning far into a music style for inspiration, hip-hop for Samurai Champloo, and Jazz/Bebop for Cowboy Bebop. Each follows a cast of cool but also dysfunctional characters that are similar to each other. Both series involve the characters messing around for the most part in random events that can be both heartfelt and silly.

If you liked Bakemonogatari add

...then you might like Mahou Shoujo Madoka★Magica add

Both made by shaft with similar amount of dialogue, pacing, and art style weirdness.

If you liked Yojouhan Shinwa Taikei add

...then you might like Yoru wa Mijikashi Arukeyo Otome add

Movie made by the same director and based off of novels written by the same author. The art style is the same with a similar form of comedy as well as multiple nods and references to each other.

If you liked Cowboy Bebop add

...then you might like Space☆Dandy add

Both in a futuristic space setting where the main cast is a group of bounty hunters. It is pretty random like a lot of Cowboy Bebop's episodes and the crew is often dysfunctional where they always mess up and can never seem to get a bounty.

If you liked Kaguya-sama wa Kokurasetai: Tensai-tachi no Renai Zunousen add

...then you might like Komi-san wa, Comyushou desu. add

A comedy manga that is presented in a bunch of short skits that is similar to Kaguya-Sama.

If you liked Kimi no Na wa. add

...then you might like Tenki no Ko add

Also directed by Shinkai, has both supernatural and romance elements with gorgeous visuals and storytelling.