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Hello, there!
Thanks for your fresh ideas and information every time.

First of all, I need to make sure that the sentence below is cited from an English related society on the web, which is "Socitey of English Teachers in Korea".
Here is the question.
What is the exact meaning of the sentence below?
"What had he said that was so funny?"
If you're a native speaker of English(I'm not), do you sometimes use this kind of sentences? If then, can you make up some sentences having gramatically similar/ same strucutures?
My understanding of the transformation procedure is,
"He had said something that was so funny."
"He had said what that was so funny."
"What he had said that was so funny?"
"What had he said that was so funny?"
Did I make a correct analysis?
It seems to be unusual that the pronoun(something in this case) in front of the relative pronoun(that) is replaced to the wh-form(what).

I see a problem here, and that is that the two verb elements are not in the same tense:
"Had he said..." is in the past perfect, whereas "was funny" is in the simple past.

Oh! You're right.

Then it looks a little funny that the ungrammatical sentence appears in a textbook for high school students.
By the way,
if we replace "What had he said" to "What did he say", isn't there any grammatic and semantic problems?

mr109 wrote: My understanding of the transformation procedure is,
"He had said something that was so funny."
"He had said what that was so funny."
"What he had said that was so funny?"
"What had he said that was so funny?"
Did I make a correct analysis?
It seems to be unusual that the pronoun(something in this case) in front of the relative pronoun(that) is replaced to the wh-form(what).

Your analysis appears to be correct. Moreover, both "What had he said that was so funny?" and "What did he say that was so funny?" are grammatically correct.

He had said something that was so funny. (Underlying Form)
He had said WHAT that was so funny. (WH replacement)
WHAT he had said that was so funny. (WH movement)
What HAD HE said that was so funny. (Subject-Verb Inversion)
What had he said that was so funny? (Surface Form/question)


By the way, "What" can replace the pronoun 'something' or both the pronoun and its modifier 'something that was so funny'.

He had said something the other day that was so funny. (Underlying Form)
He had said WHAT the other day. (WH replacement)
WHAT he had said the other day. (WH movement)
What HAD HE said the other day (Subject-Verb Inversion)
What had he said the other day? (Surface Form/question)


All the best,
Casio

Hi, Mr109.

I think Casiopea already explained the heck out of the grammar of your interesting sentence (aren't people who can do that impressive? I always feel like a language novice when I read a good explanation someone else wrote.)

But perhaps you'd still like to know how a sentence like yours could be used. When I read your sentence for the first time, a possible scenario, perhaps from a novel or something, came to mind:

It was time for the introductions. Mr. Oh was nervous, because it was the first time he'd been surrounded by so many native English speakers. Would he make a fool of himself? He hoped not. Suddenly, hands were being thrust at him to shake. As each man's hand was offered, its owner said his own name.
"Nathan Smith." Said a young blonde man.
"John. John Harrison." Said another.
"Yoo-Suck. Oh Yoo-Suck!" Said Mr. Oh enthusiastically, copying their simple style of self-introduction. Without warning, the men around him exploded in laughter. Poor Mr. Oh was bewildered. What had he said that was so funny?

Hee! Thanks for the laugh and the explanation EH

I appreciate your fantastic explanation with the authentic situation I am familiar with. Very understandable!!