Songfacts®:

• Bruce Springsteen learned his craft in his high school years as a member of the 1960s band The Castiles. The group played a variety of venues and recorded two original songs at a public recording studio in Brick Township, New Jersey, for 50 bucks (Here's one of them). In 2018, George Theiss, the only surviving member of The Castiles besides Springsteen, passed away, leaving the singer as the "last man standing" from the group. Here, he recalls his memories playing at:
  
  Knights of Columbus and the Fireman's Ball
  Friday night at the Union Hall
  Black-leather clubs all along Route 9
  
  Springsteen recalled to Apple Music: "Those were some of the deepest learning years of my life - learning how to be onstage, learning how to write, learning how to front the band, learning how to put together a show, learning how to play for all different kinds of audiences at fireman's fairs, at union halls, at CYO [Catholic Youth Organization] dances, and just really honing your craft."
• Letter to You marked the end of a long period where Springsteen felt unable to write specifically for the E Street Band. He told Rolling Stone the death of George Thiess sparked the change and his reflections on mortality spurred him to write many of the record's tunes, including this song and "Ghosts."