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Is there difference between, say, "He knows Shakespeare" and "He knows his Shakespeare?"

When should the former and the latter be used?

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The first is a casual and short way to say one is familiar or knows the author. The second statement, which is also casual, is emphasizing that one knows the works of the author in depth.

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The first asserts knowledge, the second implies expertise. Using the personal possessive pronoun indicates that "He" of the sentence has made a particular and close study of "Shakespeare." This would be more likely to be used for someone who clears a column on Jeopardy than for someone who teaches English literature. It's vaguely jocular.

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