I believe that these five sentences may be correctly punctuated. Do you agree? I'm using quotes around the movie title (as The New Yorker does) instead of italics. Although it may be ugly, I’m banking on all punctuation as being correct. Please, no suggested recasts. I thank you for any feedback.

  1. He said, “I thought I heard Judy say, ‘ “Gone with the Wind” ’s cast was unparalleled.’ ”
  2. Joe said, “ ‘Gone with the Wind’ ’s cast was unparalleled.”
  3. “Gone with the Wind” ’s cast was unparalleled.
  4. “ ‘Gone with the Wind’ ’s cast was unparalleled,” Joe said.
  5. Joe said “I thought I heard Judy say, ‘It was "Gone with the Wind” ’s’.”
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    The New Yorker's punctuation (and, indeed, Use of English in general) is idiosyncratic. Just use the customary italics for titles. – Andrew Leach Jan 2 '14 at 9:34
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    Full spaces between quotes or before an apostrophe is not something I have seen before. Not even in French. – RegDwigнt Jan 2 '14 at 11:25
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    @AndrewLeach: It's idiosyncratic on the computer, but if you're writing it by hand, it's important to know the rule. ;) – Sara Costa Jan 2 '14 at 14:35

It is indeed ugly, and technically, I'd say you're within your rights to write your sentences that way. Having said that, I'll side with George Bernard Shaw's criticism of apostrophes as "uncouth bacilli". I think your sentences are replete with uncouth bacilli, for the sake of someone's (whose?) propriety.

I would not jump through the hoops of punctuation as you've done. I would hope common sense would allow rewrites as follows:

He said, “I thought I heard Judy say, ‘“Gone with the Wind's” cast was unparalleled.’”
Joe said, “'Gone with the Wind’s' cast was unparalleled.”
“Gone with the Wind's” cast was unparalleled.
“‘Gone with the Wind’s' cast was unparalleled,” Joe said.
Joe said “I thought I heard Judy say, ‘It was "Gone with the Wind’s’.”

There is no space between double and single quotation marks.

James Harbeck writes

Many apostrophes are really only there for condescension. Apostrophes do have one consistent function: The grammar griper brigade likes to use them as the tips on their cats-o-nine-tails. Theyre excellent tools for condescension. Dont tell me theres no classism in terms like "greengrocers apostrophe" (for apostrophes in plurals). Such agitation over a little mark that conveys nothing new — other, evidently, than, "This person doesnt know how to use apostrophes." Its a fashion infraction on the level of wearing white after Labor Day or socks with sandals.

Should the Apostrophe Be Abolished?

“England and America are two countries separated by a common language.” -George Bernard Shaw

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    If 'common sense' were to prevail at all surely you would say 'the cast from/of "Gone with the Wind". If the French can manage perfectly well without a possessive case all of the time, why can't we simply abandon it when the interests of clear auditory amenity dictate. – WS2 Jan 2 '14 at 12:15
  • @WS2 - I've spoken French all my life, and never even noticed that what you've stated is correct. I had to think through several possessive phrases to come to terms with that. The degree to which we take a native language for granted is stunning. – anongoodnurse Jan 2 '14 at 13:56

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