 If you liked
Cowboy Bebop
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 ...then you might like
Wolf's Rain
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The stoty is really different, but the feeling is colse, exspecially the ending gives the same moral. The the song writer is the same, and it gives the sipirt to the show.
Both are produced by Bones around the same time and have soundtracks created by Yoko Kanno, which means...both are super great quality and feel similar.
The feeling is the best in these two anime. Freedom. That's what you see here. The art is also somewhat similar. So nothing in particular, but similar in all small aspects.
Even though the settings are completely different - I felt the same atmosphere when I watched them.
If you like one - you will like another kind of thing. Wolf's Rain is more main plot heavy, rather than being a collaboration of stories like Bebop.
Just the same vibe, kind of retro animation (which in both series is absolutely amazing) and the same screenwriter Keiko Nobumoto