Songfacts®:

• Chris Stapleton wrote this outlaw rocker with his former SteelDrivers' bandmate Mike Henderson. The SteelDrivers included their version of the song on 2008's The SteelDrivers, released via Rounder Records. Stapleton explained to NPR why he re-recorded the song for From A Room: Volume 2:
  
  "It was my old bluegrass band I used to be in. We recorded that song in that band, but I've always continued to play that song even when I'm not in that band, so it got time to be recorded again like, 'Listen, I still play this song every night. We should record it.'
  
  One's got a banjo on it, and the other one's got a little Bo Diddley drums underneath it. It's still the same song at its core, it's just a song I've always loved. I love to play it live, it always goes over live. It was originally written more in my head like we're doing it now, than what we did back with the SteelDrivers. Richard Bailey is a master of being able to play a banjo on anything, so he was able to take that song and turn it to what it was with the SteelDrivers."
• Lyrically, "Midnight Train to Memphis" finds Stapleton in jail, serving a 40-day sentence for a fine he was unable to pay.
  
  Forty days of shotguns and barbed wire fences
  Forty nights to sit and listen
  To the midnight train to Memphis
  
  Stapleton gets to listen to the rumbling sound of a distant train every day of his time in prison.