Analysing a sentence written by Woody Allen

This sentence is really not that different from

That’s why when she smiled although I was sad I smiled too.

It could do with some commas, which becomes clear in the shorter version. All I have done is substitute:

• "she smiled" for "included in last week’s A-list was a writer-director in cinema with a long list of credits"
• "sad" for "unfamiliar with the titles"
• "smiled too" for "anticipated a particularly scintillating Labor Day"

Grammatically, the only thing making it complicated is using long phrases without any parentheses or commas to help you identify the sort of nesting in the sentence.

If I put commas in the short version:

That’s why, when she smiled, although I was sad I smiled too.

I can try putting the same commas in the long one:

That’s why, when included in last week’s A-list was a writer-director in cinema with a long list of credits, although I was unfamiliar with the titles I anticipated a particularly scintillating Labor Day.

And I think that makes it more readable.