Hmm. Going solely off the fact that you like Cowboy Bebop, my personal favorite anime... You can always start with one of the creator, Shinichiro Watanabe, other works. Samurai Champloo is his best I'd say after Bebop, and Space Dandy is likely his most popular. Terror in Resonance is an excellent, albeit short series.
Wolf's Rain, however, is the only show from the studio who created Bebop, that has everyone involved from the music and the artwork, all the way to the story. It's fantastic.
It seems the first stop people make with anime is FullMetal Alchemist Brotherhood, so you can start there. Trigun is also an absolute must if you're a fan of Bebop. It's similar in a lot of ways. Especially its way of telling a subtle overarching story. I'm betting you'd love The Big O, a great thriller mystery that takes place in a dystopian futuristic NYC where everyone has lost their memories from 40 years prior. A negotiator named Roger Smith (voiced by the same actor as Spike from Bebop) takes it on himself to figure out what happened.
My own recommendations.
Mushi-Shi. It's the anime equivalent of Six Feet Under. It drags you into its world with its atmosphere and never lets go. It's about a wanderer who travels into various locations when he hears of mysterious phenomenons happening. Each episode gives you a bit more insight into what exactly the mushi are. This show is art.
Gun X Sword: It took me a couple of viewings to fully appreciate this show. It's about a wandering depressed man in a tux named Van looking for a man with a claw. Simple sounding but it's a very layered world with rich characters and development. Even the filler episodes have little hidden tidbits of info advancing the plot.
Heat Guy J: I'm probably adding this because it's the show I've most recently watched. It's from 03-04 and I just had heard about it in the last couple of years. The only thing I had heard about it is that it takes place in a futuristic city where everything is treated as a commodity and advanced tech like androids are outlawed. It has some bad pacing (it's highly episodic after it sets up the story/characters) but there is a lot to like in
just about every episode.
I'll second Psycho Pass, the first season is excellent. Season Two sucks though, and the movie is a just a passable wrap up to the first season.
If you're looking for recent shows, My favorites that have came out on DVD/BR this year are Garo: The Animation, Rage of Bahamut, and Laughing Under the Clouds. Those three have excellent stories.
Can ya tell I've watched a lot of anime? Lol.
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