Trigun

Vash the Stampede is a gunman on the run with a 60 billion double dollar bounty on his head which has made it difficult for him to go anywhere without being chased and shot at. Every town he ever visits ends up being destroyed because of his pursuers, but miraculously no one ever gets killed. Meryl and Milly are two insurance agents that have been sent to find Vash the Stampede and keep him under surveillance so no more damage is caused. Meryl, who leads the pair, refuses to believe that the man they have met can possibly be the legendary gunman. This spikey haired, gangly, young man is extremely friendly, a pacifist, hates blood and suicide, absolutely loves donuts, and is a dork and a crybaby (far from a notorious outlaw). But there is more to Vash and his past than meets the eye.

Synopsis from Anime News Network