The Hep-Cat Hairless Heir to Bobby Short

“When I rehearse with my boys, I say, ‘You’ve got to know the lyrics.’ Even if they don’t sing, they’ve got to know what it means [to be] in the still of the night,” explained Chris Gillespie, resident entertainer at Bemelmans bar at the Carlyle. “You have been there—stand outside! There is no reference point except the stars, and if it’s really the still of the night, then you hear nothing.”

Mr. Gillespie, 42, was lounging sideways on a booth in a diner near the Carlyle, wearing a patterned, wide-knotted tie over a striped shirt and a blazer with aviator sunglasses peeking out of the breast pocket. Preparing for his evening set, he had ordered an open-faced tuna melt.

“I don’t need beat, I need space, I need sound schemes, I need a carpet on the drums,” he said.

Mr. Gillespie performs mostly well-known tunes by the likes of Nat King Cole and Frank Sinatra, and calls Cole Porter and George Gershwin his major influences. In order to make his renditions memorable, he tries to emphasize the poetic dimensions of his choices. “There’s nothing new under the sun; we all have heard this, we all have done this. Sure, there are others out there, but to make it my own, [it’s] my philosophical interpretation of the lyrics,” he said. When Mr. Gillespie began his late-night set a few weeks ago with “These Foolish Things (Remind Me of You),” his delicate piano playing merely acted as a backdrop for his more intense, passionate singing style.

It was a strange and winding road for Mr. Gillespie to the Carlyle. The biological son of a Dutch father and a Tanzanian mother, who gave him up for adoption when he was two, he was raised by no-nonsense foster parents in Munich, Germany.

“There was a bit of a bitter taste in my upbringing, because showmanship I always had in me, but in Germany that’s not something they take as an asset. That’s not good. What’s good is perfection,” he lamented.

At seven, Mr. Gillespie played a “very challenging” accordion piece for a hall filled with some 300 people. Yet, although his parents “went nuts” and “loved it,” according to Mr. Gillespie, a career in music was never a viable option in their minds. He attended business classes and later joined the air force, but all along he worked to “recapture melodies” on the piano that he had heard in American movies.

In 1988, after a disappointing and dispiriting encounter with his biological mother, Mr. Gillespie arrived in America, where he knew only one person—a man named Robert Brewster, whom he had previously met in a series of chance encounters. (Mr. Brewster, who is gay, first met Mr. Gillespie when he was working at an expensive clothing store in Munich. Soon after, the American “accidentally left his wallet” in a restaurant where the young musician was earning extra money playing the piano.) Once in Manhattan, Mr. Gillespie promptly moved in with Mr. Brewster, who’s now a member of the music committee at the National Arts Club.

“The cat had serious music under his belt. So I would play Strauss and he would sing, and he was so happy because he hadn’t had the chance to do all that—his boyfriend was in fashion,” said Mr. Gillespie, who has been married to his current wife, Patricia, for nine years. After a few weeks, his residency with Mr. Brewster turned sour, apparently as a result of the boyfriend’s mounting jealousy.

Dejected, alone and unemployed, he resolved to throw in the towel and return to Europe, but not before buying some stylish luggage at Bloomingdale’s. It was that very afternoon, as he was rolling his new Hartmann suitcase down Lexington Avenue, that he passed by a piano in the window of a since-shuttered restaurant called Foucher. After promising the proprietor that he wouldn’t ask for food or use of the bathroom, he was allowed to stay and play for a while, which led to a paying job at Foucher’s keys. From there, he was lured across the street to Jacqueline’s, then to the Mayflower Hotel, and then the Sign of the Dove, a stint peppered with private events at the Rainbow Room and Windows on the World. In 2001, he was brought to the Carlyle.

The Hep-Cat Hairless Heir to Bobby Short