After all these years, even after having gone through one Hell of a fandom and realizing that it really was pretty goofy -
TRIGUN
It's not as "artsy" as some titles I've gotten into since, and it has a lot of over-the-topness, but it's a fun title, has a great settinig (wild west meets steampunk meets sci-fi), and actually has a lot of philosophy - particularly regarding the varying "sacredness" and expendability of life. It's also got bada$$ longcoats and hero-wind, and weird junk happening to a moon. Vash the Stampede is so charasmatic a character that he is, even after years, still my favorite fictional character out of all of fiction.
I'll summarize it since it is an older title (first aired in 1998) and not everyone may be familiar with it:
In the far future, there is a desert world inhabited by a humanity that lives a rough, mostly old west style existance withering under twin suns. Rescources are scarce and mostly centered around mysterious power-generating "Plants" and other bits of lost technology leftover from cataclysmic crash-landing of the original colonists - "The Big Fall." On this planet, rumors fly about a mysterious gunslinger, Vash the Stampede who is rumored to be the baddest of the bad, a destroyer of cities, a wandering grim reaper who visits anyplace only to leave destruction in his wake.
After the latest Vash-blamed disaster, a pair of lady insurance agents (Meryl Strife and Milly Thompson) are assigned by their firm to find and monitor this outlaw and to try to minimize his chaos. When they do meet up with the real Vash the Stampede, he actually... tuns out to be a goofy pacifist who uses his gun to stop bandits when he has to (non-lethally) and who tires to talk his way out of sitiuations as much as possible. Great destruction follows him, but it is usually caused by bounty hunters after his head and assorted bandits in their mad rush to try to kill him!
The story deepens and darkens. Vash and the girls meet up with a gunslinging priest named Nicholas D. Wolfwood who hails from the city of December who is trying to protect an orphanage and who, strangely enough, does not actually resemble Santa Claus... and we find out about a group of asassins sent after Vash as part of a plot by a genocidal maniac out to wipe mankind from the planet, Vash's connection to the Plants, to the history of the world and to the destruction of a city called July many years ago.
That's a basic summary witout giving spoilers. The story starts out quite lighthearted but it gets decidedly dark midway through. The manga is longer and much gorier than the anime. Some fans say it's "deeper" but I personally don't see it, in fact, I think the over the top blood of the manga actually takes away from the depth of the core story just a bit - but the core story is good in both the anime and the manga and there are bits I like of each. (A few of the important plot events I think were done better in the manga, and some I think were done better in the anime).
There is also a feature-length movie, "Badlands Rumble" that is based in the anime's version of the universe and some unspecified point in the plot and has Vash, Wolfwood, Milly and Meryl dealing with an uber-bandit named Gasback and a bounty huntress named Ameila. I think that movie's best scene is the whole bar sequence. *Grin.* Lots of weird people and Vash being, well... Vash.