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In Season 2, Episode 10, Jim proves to be incredibly demanding when it comes to getting what he wants. He visits a contemporary art gallery and asks the assistant too many questions about the current exhibition. Later, he gives Dru some vague and unhelpful instructions for assembling a sculpture. When Jim goes out to try a new Italian restaurant, his strange requests overwhelm the service staff and end up creating an emergency situation.

Jim Kempner of Jim Kempner Fine Art writes and produces The Madness of Art, a video series depicting the day-to-day activities of a New York gallery owner in Chelsea.