Songfacts®:

• This track tells the tale of a gypsy girl and of the man who must leave her to enter the "valley below." Some critics see the song as a metaphor for Dylan's crumbling relationship with his then wife, Sara Lowndes, but it was a specific experience that inspired it.
  
  When Dylan was 34 years old, he visited Saintes-Maries-de-la-Mer, France. While there he attended a gypsy celebration. The experience left a strong impression on him. "I'll never forget this one man played Russian roulette with five bullets in the chamber!" Dylan wrote of the experience. "Anyway, things went on and it was time for me to go. They said, 'What do you want Bob, as you're leaving us?' I just asked for a cup of coffee for the road. They put it I a bag and they gave it to me. And I was standing there looking out the ocean, and it was like [I was] looking at the valley below where I was standing."
• Dylan wrote the song during the summer of 1975 at a corner table in the Greenwich Village Other End nightclub. He first played it live on October 30, 1975, at a show in Plymouth, Massachusetts.
• The song sees Dylan dueting with Emmylou Harris, who also sung backing vocals on several other Desire tracks. The Country singer-songwriter was just beginning to break through into the big time when she collaborated with the folk legend. In fact after she's completed her sessions, Harris went back to working on her own album Elite Hotel, for which she subsequently won a Grammy. In a 2010 interview with Gibson.com, she recalled that Dylan didn't actually know who she was. Said Harris: "There was a fellow at Columbia that was a fan, who was like an executive producer, and I think Dylan told him 'I need a girl singer.' Don DeVito was his name and I got a call that Dylan wants you to sing, but that wasn't true because he just wanted a girl singer. I mean we basically shook hands and started recording. I didn't know the songs, the lyrics were in front of me, and the band would start playing and he would kind of poke me when he wanted me to jump in. Somehow I watched his mouth with one eye and the lyrics with the other. You couldn't fix anything. What happened in a moment was on the record."
• The song has a specific inspiration, but it's not all literal. "My feeling about the song was that the verses came from someplace else," Dylan said to Paul Zollo. "'Valley below' could mean anything."
• Amongst the many other artists who have covered the song are, The White Stripes on their 1999 self-titled debut album, Robert Plant on his 2002 set Dreamland and Roger McGuinn and Calexico for the 2007 Dylan biopic movie film, I'm Not There.
• Rob Stoner's bass contribution at the beginning of the song was because violinist Scarlet Rivera wasn't ready. Stoner recalled to Mojo magazine October 2012: "The beginning of 'One More Cup of Coffee' - that wasn't arranged for me to do a bass solo. Scarlet wasn't ready. Bob starts strumming his guitar - nothing's happening. Somebody better play something, so I start playin' a bass solo. Basically the run-throughs became the first takes."
• The lyrics of the song reflect the sense of mystery Dylan felt at the gypsy celebration. The woman discussed in the song seems to exist halfway in our world and halfway in some other. She's alluring but also has a certain amount of danger about her, as expressed in the lines:
  
  Your voice is like a meadowlark
  But your heart is like an ocean
  Mysterious and dark
• Joni Mitchell recalled a conversation with Dylan that may have provided the song title. On March 24, 1975, she and Dylan ("Bobby," as she calls him) were guests on the Queen Mary hosted by Paul McCartney to celebrate release of the Wings album Venus And Mars. They started talking about painting, and Dylan asked her what she would paint if she were to paint the room. "The mirrored ball spinning, the women in the washroom, the band," she replied. These images ended up in her song Paprika Plains.
  
  When she returned the question to Dylan, he answered, "I'd paint this coffee cup."
• Tom Jones covered this song in 2021 for his album Surrounded By Time. "Years ago I was a bit of a tearaway, finding myself in situations and with people I shouldn't have been with," he explained. "For me all these years later when I hear the line about going down to the valley below, I don't just think about the reality of going too far, but also the hangover. I can't be that person any more but I start singing that song, and I'm right back there."