Reading all the hugo award shorts chronologically part 4— Robert Bloch's "That Hell-Bound Train"

 ★ ★ ★ ★

I'd say this one is the first purely fantasy story in this list. Things like Oklahoma and New Orleans still exist— I imagine they still had diners where they made soda the old-fashioned way, and railroad spikes were still new. This one felt like a parable too, like a prototype for Adam Sandler's Click. Martin makes a deal with someone who's essentially Charon on the River Styx, a conductor on a vantablack train rather than a ferryman on a boat, who lends him a powerful watch that would enable him to stop time forever in exchange for a guaranteed ride on the hell-bound train. Martin's clever, and makes this wish to circumvent mortality... if he stops time forever he will never have to meet "death" again. 

So he lives his hobo life, almost stops time when he's drinking merrily, but seeks more. He becomes successful in his career and almost stops time, but doesn't. He almost stops time during sex, but realizes he wants a wife. He almost stops when they're married and have a son, but he realizes he wants to see his kid grow up. Just delaying and delaying, seeking an ultimate happiness. He loses it all at some point, picks himself back up again and again, only to be met with his senility and age. He is visited by the conductor before he can turn it again, and the conductor reveals it was kind of a placebo... that no one's ever dared actually stopping time forever. Having lost it all, Martin works the watch and makes the train go on into eternity, never making a stop at hell. 

In the very beginning we meet Martin's dad, who sings the song of the hell-bound train till the day he himself is struck by a train. Martin has an inkling that his dad made a deal, too, but exchanged his life for a shot or two of whiskey.

Story and list.