The End of (High School) English

Ever since Third Grade when my son's teacher and the school staff revealed
1) my son didn't understand what he was reading 
2) they had no plans to help him improve
he's fought through the battlefield of English class with whatever poor weapons we could give him.
Currently he has an extraordinary, gifted tutor and a helpful, experienced teacher.
Together they face the last battle: Senior English

Beowulf
Canterbury Tales
Macbeth 

For a reader who still prefers Dr. Seuss, this reading list strikes me as mildly insane. But if he is to graduate with a regular diploma, (which I also have doubts about) to Chaucer and Shakespeare he must go.

Since his great tutor started, I only help once in a blue moon. He continues to be more interested in the sound of words than the meaning of sentences. As for narrative and subtext - 
let's just say his tutor needs to be the genius she is.
About The Canterbury Tales he remembers "When in April the sweet showers fall" and the titles The Pardoner and The Wife of Bath  
but when I ask what happened in the stories, he says 
"I forgot." (They studied it around Thanksgiving)

About Beowulf he says, "Did he ever have a battle with Grendel?"
(started this in September I think).

He's currently reading Macbeth, and remembers a fair amount, only slightly muddled:
"Macbeth is supposed to kill King Duncan in order to become Thane of Cawdor and King hereafter.  Macbeth's sidekick Banquo doesn't like it. He says Macbeth cheated to win those titles. Macbeth decides to kill Banquo and his son Fleance. Banquo dies but Fleance. Wait, he tells the murderers to kill Banquo and his son. The witches Macbeth will not die except at the hands of somebody who was not born of woman. They also say that the forest will move to Dunsinane hill. The forest does move. And Macduff says that he was not born of woman, but that he was untimely ripped from his mother's womb or something so Macbeth tries to deny the prophecy but he can't. And therefore he dies."

To get the regular ed diploma, you take the regular ed classes. 
I have more questions than answers about what all that means
and whether it makes sense for every student. 

What about you? What is your experience as student, parent, guardian, teacher, etc.?

Spectrum Mom