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If you liked Cowboy Bebop add

...then you might like Samurai Champloo add

One trait that sets Shinichiro Watanabe’s work apart is his refusal to accept this Japanese conformity. In his anime, all of the characters define themselves by their individuality, fighting for themselves and ONLY themselves in a vast and lonely world. In Cowboy Bebop, the characters were thrown together by chance and stayed together only as long as convenience allowed. Although the anime was for the most part an action comedy, even the hilarious moments were subdued by this profoundly forlorn undercurrent of internal solitude. Samurai Champloo has a very similar feel; in the series, three misfits who would otherwise have nothing to do with each other are thrown together by coincidental events. The characters then proceed to engage in a variety of episodic escapades, finally culminating in a suitably climactic and suspenseful conclusion. This basic plot structure, combined with Watanabe’s trademark freeform style, makes it easy to draw comparisons between the two works, despite the radically different settings. In any case, if you liked one, watching the other is practically a matter of course.

If you liked Paradise Kiss add

...then you might like Nana add

Ai Yazawa’s work is so distinctive that no one could mistake Nana and Paradise Kiss as being written by anyone else. While the series aren't perfect, they can be considered one of the frontrunners of modern shoujo romance. I emphasize modern because of how backward and traditional other romance anime seems when compared to Yazawa’s work. While other shoujo series are still mucking about with idealistic conceptions of the One True Love, the feelings of Yazawa’s characters are much more complex, layered, and believable. Nana and Paradise Kiss are amazing not only for convincing us that its characters love each other, but for convincing us that we know why they love each other.

If you liked Texhnolyze add

...then you might like Pale Cocoon add

Both science-fiction series show humanity using technology to shut itself off from reality. While both are fairly downbeat, both shows have intelligent and affecting storylines that should appeal to the same audience.

If you liked Serial Experiments Lain add

...then you might like Pale Cocoon add

Both Pale Cocoon and Serial Experiments Lain are concerned with society moving from the "real" world into a realm dominated by technology. The two series are concerned as to whether this is a step in the direction of progress, or a retreat from what makes us human.