We start off with a disclaimer of an introduction, perhaps to allay our avoidance of the song due to its title: "Listen to my story/ It's got a happy ending."
It starts of lugubriously, then the drums kick in and, despite the dreary content of the song, an up-tempo rhythm begins.
And I do mean dreary: "Every night, I sat up in my room/ Feeling the silent gloom/ Of my lonely heart." [We pause to take note of the decision to have a rhymed couplet followed by an unrhymed line. This is rare in popular music, and perhaps indicates that the speaker, too, feels like an unrhymed line, while everyone else is in a couple(t).]
We also meet the isolated, alone-in-his-room character we encounter so often in Simon's songs with Garfunkel, like "I Am a Rock," "A Most Peculiar Man," "Patterns," and even "Kathy's Song." He also shows up as Sonny in "The Obvious Child."
Our speaker here is not entirely lonely. This sad young man is befriended by a "a voice [that] cried out/ From deep inside." Rather than offer encouragement, the voice suggested: "Why don't you cry, little boy, cry?"
So he does. A lot. The line "and so I cried" repeats several times in the chorus... for a total ten utterances of the word "cried."
The next verse finds him so despondent in his isolation that he nears the brink of utter despair: "I'm alone in this world/ Without the love of a girl/ Sometimes I felt that I could not go on."
The voice is still no help: "Everywhere I went/ That voice inside of me/ Kept saying 'Cry, little boy, cry'."
If he is crying literally everywhere he goes, he is really going to stay alone, we think. Misery loves company, but often does not find it. Also, it does not add to his attractiveness that he thinks of himself as a "little boy," defenseless and helpless. Today, the boy's parents would probably intervene and guide him toward therapy. Or at least get him a hobby.
Now, the promised "happy ending" arrives, in the form of another person who was "lonesome, too": "You seemed to understand just how I felt."
This relationship progresses remarkably quickly; the next thing we know, they are somewhat intimate: "And as I kissed you then/ I knew I loved you when/ You said, "Don't cry, little boy, don't cry."
And he agrees that he won't. Just as vehemently and repeatedly as he cried before, he now insists, "I won't cry." Happy ending achieved.
Is this a stable relationship? Probably. Is it a healthy one? That is another matter entirely. If anything should happen to her, we can only brace ourselves for what would happen to him. His entire happiness depends on her; hers, on making him happy. It's a model of what we today call codependency.
However, having been a teenager myself, I can certainly commiserate with the speaker. The feeling that everyone else is in a relationship except you and it will never happen to you so you will always be alone is both powerful... and popular. Well, maybe a better word is "widespread." This feeling also affects adults, of course, as demonstrated in the opening scene of the movie Bridget Jones's Diary.
Now, the question of whether or not to cry at all comes up again in Simon's solo work. The speaker of "Boy in the Bubble" consoles the listener: "Don't cry, baby don't cry." A later speaker, in "Further to Fly," refers to that one as "the great deceiver who looks you in the eye/ And says 'baby, don't cry'."
Yet another comes along in "The Cool, Cool River," resolving this dispute: "Sometimes, even music/ Cannot substitute for tears."
In other words-- if you have to-- cry, little boy. Cry.
Next Song: The Lone Teen Ranger