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 music business, and not let the money get to you?’” Crockett told the crowd. “Man, I just spend it.”

The Café Carlyle residency, which Crockett played solo and acoustic, meant as much to the South Texas native as his March slot headlining RodeoHouston to upwards of 50,000 people. The bridge in Central Park where Crockett first busked in New York in the late 2000s is only a few hundred yards from his residency.

“I found out that everybody in Brooklyn hates the G Train,” he said of his New York busking days. “Those trains only come every 10 or 12 minutes. But, see, for a vagabond like me, that’s exactly where I want to be. Because I had your ass.”

The Carlyle Hotel is perhaps best-known for Bemelmans, the cocktail bar that hosts the most exclusive Met Gala afterparties each May and was once a frequent haunt of Waylon Jennings, one of the handful of artists Crockett reflects in his own career. Before Crockett’s first 90-minute set of this residency, he passed the time in his room at the Carlyle alongside his wife, Taylor Day Grace, who saw Crockett off with a simple suggestion: “We should probably have some fun.”

Then, Crockett carried his guitar to the stage and kicked off “Game I Can’t Win” from his Lonesome Drifter record. It’s a tune about learning and dodging the high-stakes, high-money music industry, with lines like “You didn’t hear it from me/they don’t like it when you’re free/Your check ain’t never coming in/I’ve always loved a game I can’t win.”

“I realize a lot of you paid good money to be here, and I apologize for that,” Crockett cracked from the stage to the approval of the crowd.

His set was heavy on songs from both of the albums he dropped in quick succession this year, Lonesome Drifter and Dollar a Day. Highlights included “The Life of a Country Singer” and “Woman in a Bar,” the latter of which Crockett dedicated to Grace. While he passed on addressing his late-summer row with Gavin Adcock, Crockett had no problem reminding the crowd often of his country music bona fides. “I ain’t left, and I ain’t right,” he asserted. “I’m on the road.”

The notion that the crowd was only filled with regulars is misguided, though. A sizable portion were longtime Crockett fans and some traveled from states away to catch the show. Representatives from New York-based Island Records — the label on which Crockett released both Lonesome Drifter and Dollar a Day — mingled, too. Crockett delighted in the two albums, both produced by Shooter Jennings (plus a third on the way in the spring, which will make three albums in a year on Island).

“I do business in New York, because New York can tell Nashville what to do,” Crockett said, “but Nashville, as much as they want to, cannot tell New York what to do. And, being a Texan, I like that.