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When Ms. Kim set out to design the cover of “Fresh Complaint,” a 2017 story collection by Jeffrey Eugenides, a writer she had long admired, her desire to impress him got in the way at first, she said.

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Drake’s provocation shook Lamar out of stasis, reignited the writing prowess that made Lamar the only rapper who has ever won a Pulitzer Prize and sparked one of the most intense back-and-forth feuds ...