#16 Art
Art was an American train conductor in the 1920’s. He did some shady things like sleep with people’s wives and smuggle alcohol (a lot of alcohol), but he was still kind, generous and charming. One day his train accidentally crashed and now he’s dead.
The angels running Heaven (while God deals with the rest of the world) deem him not quite good enough for a nice ‘retirement’ in heaven but not really corrupt enough for hell. They decide to put him in a menial labor job, namely transporting souls to and from heaven. There are other people like him with the same job, of course, so he specializes in the souls of anyone under 1 year of age. His train is now giant, invisible and infinitely long to accommodate every soul.
Art is pretty bummed out by the whole trip back to heaven, but he’s mostly just thankful that the away-train is less full than it was when he first started the job.