Creative misinterpretation and absurdist abstraction are two specialties of Craighton Berman, who illustrates the table of contents for In the Modern World. The Chicago-based designer savors the opportunity to misconstrue the fine articles of Dwell while also being able to comment on the work of design-world giants.

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We put the same four questions to everyone we talked to for the Now 99 to learn what they’re inspired by and what they’re totally...