For the story "Iron Horse" by Shariann Lewitt, for Fantastic Stories magazine.

 Gary Shockley (with and without beard) was the model for both men - the train conductor and the guy wandering down the tracks.  Thus he is running himself over.  Of all people, Gary is one who appreciates the surrealism of that idea.

Since Interaction (Worldcon 2005 in Glasgow), this painting has been in the collection of R. Carl and M. Hayden.