Charley Crockett is making a career out of being underestimated, either by the business or his very own fans. This past week, he proved that again with a three-night residency at one of Manhattan’s most exclusive and longest-running supper clubs, the Café Carlyle on the Upper East Side.

This is a club where New York’s social elite have shown up since 1955 to wine and dine and be entertained, where $150 will get you in the door and $200 will reserve one of the roughly 100 seats available for dinner. The menu consists mostly of a caviar list and a $95 per person prix fixe. The walls in the room are decorated with murals by Oscar-winning French artist Marcel Vertès. Its clientele has money, and Crockett knows how to speak the language of money.

“I love being asked, ‘How do you navigate the

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