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If you liked Cowboy Bebop add

...then you might like Samurai Champloo add

character-based anime where with each episode you get to know more about the characters. On top of that, both are style-drive where that style is created through music – Cowboy Bebop is Jazz and in Samurai Champloo is Hip-Hop.

If you liked Cowboy Bebop add

...then you might like Seihou Bukyou Outlaw Star add

character-based anime where with each episode you get to know more about the characters. in both shows a good amount of action takes place in space, both of the main characters have a special weapon, caster in OS , psychogun in Cobra, in both shows main characters have a trusty sidekick, in both shows there is a plot involving a search for a mysterious artifact,