It's Isaiah 21:1-12; together with Daniel chapter 5 :) Bob once dropped a hint of it being like an exercise in telling a story in reverse. That's what you can see in Isaiah 21. That starts out with the winding howling (symbolically). This song has the wind howling at the end. Prophetically, this section of Isaiah is the lead-up to the downfall of Babylon - a powerful, spiritistic city-state in ancient days, one which held Jehovah's people captive; and one where the grandfather of the king had robbed Jehovah's temple. Now here was his grandson, mocking God, by having a drunken party, swilling wine from the cups that were once for temple service, while praising false gods. While the king, his grandees, concubines, etc. were partying inside; the man upon the watchtower could see horses/steeds and riders, etc. approaching from the outside. By surprise, the empire of Babylon fell that night........This foreshadows what is happening now with "Babylon the Great", of Revelation chapters 17 and 18. Like ancient Babylon, this is an empire of FALSE religion, which pains Jehovah and His people too - only Babylon the Great exists on a much bigger scale: Metaphorically, it is Satan's world empire of all FALSE, anti-scriptural, spiritistic LIE-teaching, and evil-practicing FALSE religions. Do businessmen drink its wine? Of course they do. The world's FALSE religions mean big business. What of now though? The spiritual wind is howling....clearly God's warned of punishment of "Babylon the Great" is near. Like its namesake Babylon of Isaiah 21 and Daniel 5; it too will fall, all of a sudden. Armageddon from God against the stubbornly and heinously evil will follow quickly after that. There are those as if upon the watchtower, sounding out these scriptural warnings to the world. :) If you're still "inside" any of the FALSE religions of "Babylon the Great", heed Jehovah's warnings at Revelation 18:4,5; and "get out of there, my people", quickly, before it all goes into its final, crashing fall - (“because the hour is getting late”) !! After that coming fall of Babylon the Great, and after God's Armageddon Day, which will follow it; THEN there will be TRUE peace on earth here - and everything will be good again, like it was in Eden. (Or...."We've got to get ourselves back to the Garden. :)
As Christ explained to Pilot, he was only for the Kingdom of God, the base of which is not of this world, and is “not from this source” - it is heaven based. (John 18:36) After Armageddon, God’s Kingdom will be extended down to this earth, as it’s only Rulership (Daniel 2:44). Then things will be good again. Even if this was not Bob’s original intention, everything in this song fits that scenario of Isaiah 21, Daniel 5, and our day, with its building Revelation 18. The conversation, between the joker and the thief isn’t one found in any of those verses, but is a great artistic take-off, wherein the imaginary speakers get to add more meaningful description to the scene - of both then and now.