This track, sent to Simon as an instrumental by a friend, was what sparked his whole Graceland odyssey.
First, the title. The "gum" in question is not chewing gum, but rubber. In some parts of the world, "rubber bands" are called "gum bands." "Gumboots," then, are rubber-soled boots, as opposed to leather-soled ones. The title came with the instrumental, and so bears little if any relationship to the song itself; if anything, it might reflect the bouncy rhythm of the tune.
The chorus of the song is the meaning: "You don’t feel you could love me/ But I feel you could." Each verse discusses a potential relationship that one party feels is possible and the other one... not so much (That second person could be right, though!).
The third verse's couple is easiest to parse. The man is "walking down the street" when he is greeted by someone who seems, shall we say, surprised by the obvious; by her observation, we see that she does not appear to be the brightest bulb in the lamp, even if she is gregarious and charming. But his response reveals a rich vocabulary, with words like "astute" and "institute." He is possibly multilingual, as he addresses her as "senorita." A relationship between two such mismatched intellects is a non-starter, right?
Not necessarily. While we might assume that the swifter one might dismiss the slower one, it is he whom we find reassuring her: "You don't feel you could love me, but..."
In the first verse, we have two friends talking in a cab. At first, it seems like the friend with the breakdown is not necessarily in the car, but then the word "you" makes it clear that he (or she) is, and is also the one he is "having this discussion" with.
As he is "rearranging" his position on his friend's nervous breakdown, which implies he had made a decision about it, but is now reassessing that "position." His question reflects this ambivalence. "Breakdowns come and... go" implies "OK, so it's over now, whatever," while "what are you going to do about it?" means "How are you going to make sure this doesn't happen again-- therapy, medication, yoga, what?" and indicates ongoing concern. He is so unsure about what to make of his friend's panic attack that he is at once dismissive and almost pushy-- "...That's what I'd like to know!" As if the other person's breakdown unresolved response was now his problem!
Usually, if someone has a nervous breakdown, people are hesitant to enter into (or ramp up) relationships with them right after. And yet the very next line is: "You don't feel you could love me, but I feel you could." This might be a nervous response on the part of the speaker, perhaps rushing in to fill the void in his friend's life. In this case, reassurance is taken a step too far, and "You know I'm here for you" might have been a less provocative, more appropriate response to the breakdown.
The second verse is the most abstract. How does one "fall into a phone call"? Perhaps the person who answered was not the person for whom the call was intended, but a conversation is struck up anyway; this often happens to me when my wife's friends call-- I end up chatting for a moment before passing the phone on. In any case, "falling" indicates surprise, as in "falling in love" or "falling for a trick."
"Believing I had supernatural powers/ I slammed into a brick wall." Everyone has overestimated his or her abilities at some point; a quick glance at the videos on failblog.org reveals this malady is especially common in teenage males. Somehow, in the course of this unexpected phone call, the speaker tried to solve a problem and be a hero, but ran into an unexpectedly immovable obstacle (much like the earlier scene in which he tries to solve a friend's breakdown with a come-on.) Say my wife's friend called to vent about a personal matter and I, instead of commiserating briefly and passing her on, dared to offer my own opinion. I would definitely hit a brick wall (or have one dropped on me).
OK, first the phone call itself was thrust upon the speaker, then his attempts to help were rebuffed, and now he's just upset: "I said, Hey, is this my problem? Is this my fault?" Well, it wasn't... but now he has inserted himself into the situation and, characteristically, is blaming everyone else for not appreciating his compassionate genius-- "If that’s the way it’s gonna be/ I’m going to call the whole thing to a halt!” Imagine instead of just apologizing, "Sorry, I was out of line," I said to my wife's friend, "Well, that's the last time I try to help you!"-- as if anyone has asked for my help to begin with.
Just as quickly, our speaker sees the error of his hubris and protest that, in fact, he is really a decent guy: "You don’t feel you could love me/ But I feel you could." This time, the sentence comes across as pure arrogance: "Come on, I was only trying to help!"
And so we come back to the third verse. The speaker-- having failed to be helpful with a friend's psychological trauma and then having failed by helping when his help was not requested-- now meets a simple-minded, friendly woman. Maybe they will end up together, maybe not. But at least this time, when he acts out of hand, she might be too slow to catch it, and he might be able to correct himself before she notices he should. And maybe he will learn that, despite his intellectual superiority to her, she is able to take care of herself now just as she was before she met him.
Next Song: "Diamonds on the Soles of Her Shoes."