Songfacts®:

• "Tombstone Blues" is a fast-paced, two-chord blues song that confronts the listener with the harsh realities of life and death. It's been interpreted many ways, with some seeing it as a general meditation on mortality and the meaning of life. Others hear the song as a commentary on the then-escalating Vietnam War.
• The king of the Philistines his soldiers to save
  Puts jawbones on their tombstones and flatters their graves
  Puts the pied pipers in prison and fattens the slaves
  Then sends them out to the jungle
  
  In the Book of Judges, Samson is a Hebrew strongman chosen by God to lead his people against the Philistines. Empowered by the Holy Spirit, he performs incredible feats of strength, including slaying a thousand Philistines with the jawbone of a donkey.
  
  On one level, the line may be a literal reference to the Philistine practice of putting jawbones on their tombstones to honor their warriors. On a deeper level, it can be seen as a symbolic commentary on the futility of war and violence. The "slaves" that the king sends "out to the jungle" may refer to the American soldiers President Lyndon B. Johnson sent off to fight in Vietnam.
• The sweet pretty things are in bed now of course
  The city fathers they're trying to endorse
  
  Dick Taylor of the UK group The Pretty Things thinks the opening line is a nod to the band. "Bob Dylan was very friendly with Brian Penderton our rhythm guitarist," he told Uncut magazine.
  
  One time Taylor was in the Blaises club and British blues singer Dana Gillespie came up and said Dylan wanted to know if Penderton was around. "I thought I was going to be invited to join their table, but he only wanted Brian," Taylor recalled. "But we did all get invited to a show Dylan did at the BBC."
• Dylan laid down 12 takes of "Tombstone Blues" at New York's Columbia A Studio on July 29, 1965. The last of these takes was released on Highway 61 Revisited a month later.