There have been many memorable concerts by Billy Bragg over the more than 30 years he’s been performing. His shows always combine political anthems with romantic love songs, and his appearance here at the Neptune on Wednesday will no doubt do the same. But among the ranks of Billy Bragg fans, there is one show — in Chicago, in October 1998 — that stands above the rest.

Toward the end of that night, Bragg sang some of his most intimate numbers, including “Greetings to the New Brunette” and “Must I Paint You a Picture.” While Bragg is always emotional onstage, this night he seemed particularly moved, almost broken. “Part of performing is not just coming out onstage and talking,” he told the crowd, which included Bill Wyman, who wrote about it in the Chicago Reader. “A lot of these confessional songs are important, because the feelings, after I sing the songs, come back to me, as well.”

Bragg always talks to the crowd a lot during his shows, so that didn’t seem that out of place, nor did his joke about being an “A-hole” sometimes. But he went on: “The woman I wrote the last three songs about got married today. She got married at 3 p.m., England time.”

Among Billy Bragg fans, this show is legendary, but it is also typical of how Bragg approaches his work, and life: open, honest, strident and always emotional. He’s an avowed socialist, which sometimes overshadows his songcraft. “I’m not a political songwriter,” he once said. “I’m an honest songwriter.”

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As he’s aged, Bragg has also become a skilled interpreter of other songwriters as well. While he’s always been a star in England, in the U.S. he is best known for a series of albums he made with Wilco singing Woody Guthrie songs. Their first, “Mermaid Avenue,” came out in 1998, and its acclaim and sales success had led to two additional volumes with more Guthrie tunes. All are brilliant.

Bragg’s latest solo release is titled “Tooth & Nail” and it was recorded in just five days with producer Joe Henry. It’s one of Bragg’s darkest albums, without much of the upbeat pop of his early career.

Bragg is 55 now, and there is a weariness in many of these new songs. “My journey has been so hard lately,” he sings in “January Song.” It’s a painful moment for a listener, but like the best of Billy Bragg onstage, it’s a human moment, with sincerity that makes a listener feel connected. In a moment, you are back with him, “3 p.m., England time.”

Charles R. Cross: therocketmagazinelives@gmail.com