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He claimed to part company from the communist Pete Seeger (his buddy when he wrote this song), so that's one plus point. Seeger really liked the chorus. But maybe McLean caught on:

The funny thing about the sing-a-long thing is, and I suppose I can tell you this, Pete Seeger was a communist and he was really a communist. He wasn't just a had been one or whatever; he was all his life. And communism and fascism are pretty closely aligned in some ways and one of the things they want to do is get hold of your mind and get you to thinking like they do. Hitler had these youth camps and what they would do is they would SING ALONG! They’d all sing along and pretty soon they were all one, you know. So the whole left-wing sing-a-long thing was the left side of that whole thing, getting people to sing along. If you sing along maybe you’ll start to believe it.

OK, let's get into they psychology with Erik von Kuehnelt-Leddihn, Leftism Revisited:

Identity and Diversity . . . The conformist herd instinct was, for example, the driving motor behind the nationalistic gymnastic organizations of the Germans and the Slaves, so potent in the first half of this century. Watching five or ten thousand identically dressed men or women carrying out identical movements, one gets an overpowering impression of homogeneity, synchronization, symmetry, uniformity.
The demand for equality and identity arises precisely in order to avoid that fear, that feeling of inferiority. Nobody is better, nobody is superior, nobody feels challenged, everybody is "safe" Furthermore, if identity, if sameness has been achieved, then the other person's actions and reactions can be forecast. With no (disagreeable) surprises, a warm herd feeling of brotherhood emerges. These sentiments--this rejection of quality (which ineluctably differs from person to person) explains much concerning the spirit of the mass movement of the last two hundred years. Simone Weil has told us that the "I" comes from the flesh, but the "we" comes from the Devil.
Identity's other factor is envy. Envy has several complex psychological roots. There is, first of all, the curious feeling that whatever one person possesses has in some way been taken away from another: "I am poor because he is rich." This inner, often unspoken sentiment rests on the assumption that all good things in this world are finite. In the case of money, or even more so of landed property, this might have some substance. (Hence the enormous envy of peasants for one another's real estate.) This contention, however, is often unconsciously extended to values that are not finite. Isabel is beautiful; Eloise is ugly. Yet Isabel's beauty is not the result of Eloise's plainness, nor Bob's brightness of Tim's stupidity. Envy sometimes subconsciously uses a statistical argument: "Not all of us sisters can be pretty, nor all of us brothers bright. Fate has discriminated against me!"
The second aspect of envy lies in the superiority of another person in a different respect. A burning envy can be created by the mere suspicion that the other person feels superior on account of looks, brains, brawn, money, or whatever. The only way to compensate is to find inferior qualities in the object of envy: "He is rich, but he is evil," "He is successful, but his family life is miserable." The envied person's shortcomings serve as a consolation: sometimes they serve as an excuse for attack, especially if the shortcomings are moral.
In the last two hundred years the exploitation of envy--its mobilization among the masses--coupled with the denigration of individuals, but more frequently of classes, races, nations, or religious communities, has been the key to political success.

Oh, love, love, that analysis. Which is to say, I don't believe for a minute that the song was wishing for an 1950s American Pie. Oh, the irony: folk music wanted so much freedom that when it came to politics, their utopist vision easily became a tool of the left--at least in the USA. Think about it.

Excellent analysis.

“OK, let’s get into they psychology with Erik von Kuehnelt-Leddihn, Leftism Revisited:”

I’m always impressed when someone here remembers Erik von K-L.

A great thinker from the era when National Review was itself great.

folk music wanted so much freedom that when it came to politics, their utopist vision easily became a tool of the left

Peter, Paul, and Mary were furious at the mold-breaking rock & roll’s displacing of their leftist hooey from the charts.

Their song, “I dig rock and roll music,” was a blatant shriek, and hardly required reading “between the lines.”