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Ha ha! What a funny question. There is a song from the 60's rock band, The Kinks, that reminds me of Ackley. It is called Well Respected Man. It is a British rock group, so you will have to "translate" some of the words, but it is about an annoying hypocrite that is "well respected" about town, but really a jerk. See the link below for the words.
Also, another song that comes to mind is You're So Vain by Carly Simon. It is also about a person that is pretty impressed with himself/herself - "You're so vain, you probably think this song is about you......" etc.
Simon supposedly wrote this song with a specific person in mind, but over the years, many have tried to speculate as to the identify of the song's subject. Some have guessed Warren Beatty, the actor. Others have guessed Mick Jagger, David Geffin and a host of other celebrities.
The reason that these two songs could be good with reference to Ackley is because they both are about rich people. Since Cather in the Rye is not about poor people but rather young men whose families can afford to send them to expensive prep schools like Pencey Prep, these would be good songs to use.
Perhaps some younger person would have better examples from more modern times, but I'm a child of the 60's so these two songs come to my mind.
Both your question, and the anti-school atmosphere in the novel Catcher in the Rye by the recently deceased J.D. Salinger remind me of the depressing lyrics of a song by Bob Geldof's original Irish band "The Boomtown Rats" The song is called, (appropriately!) "I Don't Like Mondays" and opens with a vision of a mom/teenage girl on a typically dreary Monday morning on a schoolday. The melody is very atmospheric/minor key and the words suggest a hard-knock life in a grey impoverished estate. "Nobody's gonna go to school today" and "her momma can't stand it, and her poppa can't stand it" In the end I think she mitches off school and runs away. Sadly it was based on a girl who shot people and was banned in the U.S. Also, Pink Floyd "Leave them kids alone" from "Brick in the Wall."
"No Scrubs" by TLC
A scrub is a guy that thinks he's fly
And is also known as a buster (busta, busta...)
Always talkin' about what he wants
And just sits on his broke a**
Pretty Fly (for a White Guy) by The Offspring
You know it's kind of hard
Just to get along today.
Our subject isn't cool,
But he fakes it anyway.
He may not have a clue;
And he may not have style.
But everything he lacks
Well he makes up in denial.
Mr. Popularity by 20 Fingers
When I look at you
I go out of my mind
It's like I'm looking
At someone's behind
You make the children scream
And baby's cry
With your crusty teeth
And your blood shot eyes
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