Surprise, surpise, Wolfwood likes Trigun 
This is one of those classic anime. It's one of those gems from the late 1990's and has that look down to a T. It was created by Yasuhiro Nightow, who also did Blood Blockade Battlefont and Gungrave.
The main character is "Vash the Stampede", a happy-go-lucky cyborg who is actually the person in my avatar and not the character Wolfwood, who is another character in the series entirely. Don't ask why.
Vash has unbelievably good marksmanship but bears horrible, disgusting scars that have resulted from his pacifist tendencies - he never shoots to kill and he ends up injured severely as the price he pays for such strict principles. Along with Wolfwood, he is often accompanied by two insurance salespeople - Meryl and Milly.
There is an enormous bounty on Vash's head, which surprised those who meet him because his personality is far from that of a dangerous killer / outlaw. Vash is somewhat unaware of his past and has a type of amnesia. Apparently, he is responsible for mass destruction and murder.
As with a lot of anime, there's a more in-depth manga which I've collected over the years. The anime follows the manga fairly closely but the manga does have some key differences, like the Eye of Michael organization and some of the assassins are only in the manga (although Wolfwood's in both).
The setting is in the style of the Old West except it's on an alien planet where humans have been stuck. There is some ancient technology lying around but it's not common in civilization. Vash's origins have something to do with it but I won't spoil that part of the story here.
