It’s early on a Sunday night, and I am one of the first people at the bar where Henry Wolfe is opening for singers Eleni Mandell and Algebro. As the sun goes down I watch about 20 people filter into the small venue to watch him perform, and can’t help but be intrigued by him, taking note that his mother is Meryl Streep and of his own seemingly quiet repute.

Meanwhile, Wolfe is somewhere in Lincoln Park feasting on Chicago’s famous deep-dish pizza, according to a passing employee of Ace Bar, 1505 W. Fullerton Ave. During the waiting period, I make my way over to the bar to ask for a glass of water when a man walks up next to me. I’m surprised to see that it’s Wolfe, who has a kind smile under a well-groomed beard.

He also orders a glass of water, sans ice, and we exchange introductions. He’s a warm personality, but was tired, having been in the city for just three hours after a long drive. And this happens to be the last stop of a week-and-a-half-long tour before heading home to New York to continue work on an upcoming record. With a laugh, he says he could use a nap right there on the floor.

Nevertheless, he heads to the stage and begins to tune his harmonica and guitar. As his first song, “Stop the Train,” from the 2011 album “Linda Vista,” gently pulses through the speakers, he warns of love: “A word to the wise, don’t throw this away. ‘Cause once you do, it’s you who’ll be crying…” His voice is sweet and gritty against the delicate melody, which is visceral and stripped down. I respect that he’s solo, choosing to work with only two instruments.

Continuing his set, the light-hearted songs become progressively more complex with apparent metaphors and hints of personal heartbreak. Somewhere behind his eyes and in the way he vibrated under the lights, he goes somewhere in his mind, producing a memory through the strumming of his fingertips. He said he has been attracted to the irony of meshing emotional lyrics with upbeat tunes.

“I was kind of interested in the idea of writing lyrics that were trending toward the darker side against music that was on a lighter side,” Wolfe said. “But it didn’t seem to be working, so I had to think about spinning what is a really…sensitive and unhappy subject—that being mental illness—and trying to portray it in somewhat of a positive light. The liberation of losing your marbles.”

The subject of romantic relationships is an issue he chose to battle with songs like “Little Room,” focusing on the psychological aspects of the human condition. According to him, he wanted to look past the typical “break-up” song and explore the possibility of an identity crisis, or the relationship people can have with themselves. It’s an idea that more people should be open to relating to: entertaining the ability to struggle, and either falling into heavy despair or rising above it.

While listening to his songs, I realize it’s freezing in the bar at this point, but am too distracted by the simplicity of his message to care. He’s forthcoming in a surprisingly casual way that doesn’t try to reinvent the wheel, as so many artists attempt to do. What most artists fail to realize is their music becomes tired. Inevitably, the more they fight against it, the more ordinary it becomes, which is why Wolfe’s work is so encouraging. Though what he’s singing is melancholy, it has the breezy distinction of being urbane.

“I think where you are in life is a choice,” Wolfe said. “I was interested settling down and staying in place, or trying to move forward and exploring that dichotomy. I think at a certain point you begin to wonder what [settling down] would be like, what that would look like. But the life that I live right now isn’t conducive to being that any time soon.”

Much of his experience learning to make music has been spent studying the California state of mind during a road trip from New York to Los Angeles, he said. The works of L.A. institutions ranging from Bruce Springsteen to Eleni Mandell have had a major influence on his musicals tastes. He said pop music has impacted his creative integrity, especially work that predates the rock ‘n’ roll era of The Beatles.

It goes without saying Wolfe has been born and bred into an artistic family. His mother has three Oscars under her belt. Two of his sisters, Mamie and Grace Gummer, are actresses, and his father, Don Gummer, is an artist and sculptor. Much of his experience learning to make music was spent listening to recordings by Bruce Springsteen, Randy Newman and Harry Nilsson. The appeal of being a musician came from the independence he feels performing solo and the control of writing his own songs.

“I like writing songs,” Wolfe said. “I’ve done some acting before. Some of the same techniques as your performing as an actor, or your performing as a musician require the same kind of suspension of disbelief sometimes.”

This is how he leaves the audience after his set. They are suspended, clapping, feeling the last strumming of notes linger in the air. As silence creeps back in, all eyes remained on him. It was as if time were put on pause until he whispers through a smile, “Nobody say anything…,” and walked off the stage.