Interpretations:Rowboat Mayor

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It's a song from a drunk person ("a red Solo cup") muttering his grievances about a local authority — a father, a boss, or a politician. The "bad boy" coda ("pack of cigarettes") at the end reveals the mistrust comes from a youthful perspective. —Down10 (talk) 18:16, 4 March 2018 (EST)

Mr. Big Shot[edit]

Good ideas above by Down10! Speculating further on those lines I'm going to guess that it's about some "regular louts" working in a small business, maybe something like a car repair shop. The economy is rough ("roiling sea"). They were all just gettin' 'er done on the job together until one of them decides he's the boss ("mayor"), gets to be too bossy, and stops doing regular work. The guys have a meeting ("deposition") & decide to demote or fire him. But things go wonky when they confront him - a fight breaks out ("fighting atop..."), they kill him & the business fails (the lost gold doubloons). The narrator starts telling the story to another inmate of the prison where he's serving his sentence, but stops short & backpedals the confession ("there was never such a thing"). Maybe he'll tell it all for a pack of smokes. The song dresses the story in a nautical theme because of the (implied) word "mutiny" and all of its associations - ships, pirates, and turbulent waters. --Nehushtan (talk) 09:41, 31 August 2019 (EDT)

With the above in mind, the little boat video becomes more intriguing to me. The superimposed words now seem like the terse, crypic "hints" that David Lynch provided as DVD liner notes for one of his knotty films. FWIW, my guesses for decoding these video clues are:
  • "thinking" means the narrator is trying to figure out how to tell the story without incriminating himself
  • "Solo cup" tells us it's not about a real boat & hints that these guys are blue-collar
  • "not one later" means the would-be mayor is dead
  • "a pack of cigarettes" means that the narrator is incarcerated
--Nehushtan (talk) 15:39, 5 September 2019 (EDT)
If you're with me so far, I suggest that the finale of the song - two mournful strokes of the violin - is an elegy for the Rowboat Mayor. R.I.P. --Nehushtan (talk) 10:58, 27 October 2019 (EDT)

The Soviet Union[edit]

So, basically, to summarize, the red Solo cup is the entire Soviet Union, but before it existed. The communists are thinking of what they want in their communist empire.

The Rowboat Mayor is Russia, at least, it's visions of itself to be a truly communist country. The nautical council has decided to keep "rowing" towards their ultimate goal.

However, while fighting for this achievement, they waste their money to the spray, never to be flown up again as the USSR collapses.

Saying that the Rowboat Mayor never existed is the same as saying the communists could never reach their goal because it was unobtainable.

Honestly, I find it funny that I see this song as more about communist than "The Communist Have the Music"

Robot Parade (talk) 17:15, 12 July 2019 (EDT)

Look Me Over[edit]

I kind of think of this song as Flansburgh's answer to The Cap'm.

--Blipvert (talk) 15:24, 2 October 2019 (EDT)

I think it's a fun, silly song about people rowing around the sea in a plastic cup and one of them decides arbitrarily that they are the "mayor" of the whole thing. The others have a meeting and discuss whether this is valid, and come to the conclusion that it isn't.