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If you liked Cowboy Bebop add

...then you might like Jormungand add

Both are episodic series with lots of gun play that focus on a ragtag band of colorful personalities. Both are science-fiction series that maintain a mostly realistic and grounded tone, and both series have a child as part of the main cast whose perspectives serve as contrast to the rest of their team.

If you liked Ouran Koukou Host Club add

...then you might like Kuragehime add

Both are sweet romantic comedies with cross-dressing main characters and occasional forth-wall breaking. Kuragehime spoof otakus in a fashion similar to Ouran's spoofing of shoujo tropes, and both have fairly plain-looking, intellectual female protagonists. Both also have catchy soundtracks.

If you liked Nana add

...then you might like K-On! add

Both are slice-of-life series with female protagonists who are extremely close friends and have lots of lesbian undertones. Both feature main characters who are in a band, and both series center on rock and feature references to Western rock-stars. Also both series have a cute but naive main character who has short, brown hair and does extremely stupid things.

If you liked FLCL add

...then you might like Tengen Toppa Gurren Lagann add

Both works are coming of age stories with fluid and exaggerated animation, delightfully hammy characters, surreal aspects, a blend of action and comedy and tongue-in-cheek sexual humor. Additionally, both become less wacky and more dramatic and scary as they go on, though this is seen fairly early in TTGL, whereas FLCL makes its shift primarily in the final episode. Also, both have a rock soundtrack, both were produced by Gainax, and both are original works, without a source manga.

If you liked Koukaku Kidoutai add

...then you might like Serial Experiments Lain add

Both are cyber-punk anime with a bleak visual aesthetic, and a quiet, contemplative, female protagonist who takes morally ambiguous actions. Both works explore the impact of technology and the internet on identity, and on the connection between consciousness and people's physical forms. The works are also remarkably similar in their pacing, and use long, drawn out shots without speech and with little action to contribute to atmosphere.

If you liked Cowboy Bebop add

...then you might like Samurai Champloo add

Both are works directed by Shinichiro Watanabe, run 26 episodes and feature a strong balance of action, comedy and drama. Both are episodic in structure, have strong original soundtracks and have small central casts of vitriolic companions who serve as foils to each other. Also, both works have the main character voiced by Steven Blum in the English Dub, and both dubs are great.

If you liked Cowboy Bebop add

...then you might like Koukaku Kidoutai: Stand Alone Complex add

Both are episodic cyber-noir series with soundtracks composed by Yoko Kanno running 26 episodes. Both series feature the protagonists confronting memorable and unique criminals each episode, and both have excellent dubs. Both series also heavily feature gun-play.