Billy Bragg: His Top 5

In November 2025, Spenwood Books published Billy Bragg – A People’s History. Over five hundred pages, it covers Billy Bragg’s musical career; there’s a discography, photos, and reviews of albums and concerts. But what makes the book special is the over six hundred entries by fans. His loyal fan base writes about performances, meeting Bragg, and expressing their feelings for his work. Bragg’s connection to his fans has always been paramount, and in Billy Bragg – A People’s History, they express their appreciation. Bragg’s music is eclectic, and his fans appreciate his varied talents, vitality, and spark of originality. Whether Bragg dwells on “mixing pop and politics” or matters of the heart, he does so with energy and passion.

In this same spirit of appreciation, let’s consider the Bard of Barking’s five best songs (according to me…). Let us know your picks in the comments.

A New England

There’s no better introduction to Bragg’s music than “A New England.”   A young Bragg sings about his trying twenties and all the accompanying heartbreak and confusion that fill up those years. He borrowed the opening line from Paul Simon’s “Leaves That Are Green.”   Bragg sings, “I was twenty-one years when I wrote this song, I’m twenty-two now, but I won’t be for long.” Simon’s song is a folkie wistful gem. Bragg’s is a punk rock stunner, in which he struggles to find answers and does not fall into grunge despair.

He sings it in a thick Cockney accent filled with intensity and fire. Bragg accompanies himself with an electric guitar and nothing more to startling effect. This song launched Bragg’s career and brought him recognition. At the time of its release, Bragg said, “most people when they sing alone with a guitar sound like James Taylor or Bob Dylan. When I am performing, I’m The Clash.”

Must I Paint You a Picture

Bragg’s fourth release, Workers Playtime, is arguably his best album. “Must I Paint You a Picture” is certainly a standout track. On this one, Bragg is helped on vocals by Cara Tivey. Bragg pours out his heart and deftly reviews the complexities of relationships.

And when I see you
You just turn around and walk away like we never met
Oh, we used to be so brave
I dreamt the world stopped turning as we climbed the hill
I dreamt impossible dreams that we were lovers still

It’s a lovely ballad with one of Bragg’s most beautiful melodies.

Levi Stubbs’ Tears

“Levi Stubbs’ Tears” can be found on Bragg’s third release, Talking with the Taxman About Poetry.  This serious drama is a story about a young woman dealing with an abusive relationship. She has her mobile home, her Four Tops tape, and little hope for happiness. It’s a bleak tale, but somehow Bragg makes the drama engrossing. The protagonist “ran away from home in her mother’s best coat “and “she was married even before she was entitled to vote.”  Her husband left her, and listening to Motown is not helpful. She knows Levi Stubbs, the Four Tops’ singer, cannot come to her rescue.

Bragg adds, “Holland and Holland and Lamont Dozier too, are here to make it all okay for you,” but she knows that will not happen. Bragg tells this harrowing tale with empathy and intelligence. Lasting only 3 minutes and 28 seconds, every second is poignant and delivers a devastating punch.

Sexuality

Bragg’s early albums feature few instruments and fewer musicians. Don’t Try This at Home, however, features a polished production with guest stars, including members of R.E.M. It’s filled with wonderful songs, including my fourth pick, “Sexuality.”

Johnny Marr played guitar and helped make Bragg’s jangly tune swing. Bragg achieved his highest showing on the US Alternative charts. Over his career, Bragg achieved chart success in the UK, but not in the US. This spunky number was an exception. In recent years, Bragg has fiddled with the song’s lyrics. He changed “just because you’re gay or want a new way, if you stick around, maybe we can find some common ground” to “just because you’re they and want a newer way, if you stick around, maybe we can find some common pronoun.”

I Keep Faith

The last one on the list is a reflective tune called “I Keep Faith.”  It is from Mr. Love & Justice.  He sounds sage-like as he delivers words of wisdom and encouragement to a loved one. It has that intimacy that Bragg does better than most. His lyrics are often humorous and aren’t afraid to be complex. Here they are direct, heartfelt, and uplifting.

I know it takes a mess of courage
To go against the grain.
You have to make great sacrifice for such little gain,
And so much pain.
And if your plans come out to nothing,
Washed out in the rain,
Let me rekindle all your hopes and
Help you start again

I last saw Bragg perform in October 2024, at the Chevalier Theatre in Massachusetts. At the end of the brilliant concert, he said, “I would like to send you home with your activism recharged and your cynicism temporarily kicked to the curb. Remember, there’s a room full of people in Medford who do give a s**t about this world. Music has the power not to change the world but to make you believe that the world can be changed.”

-Vincent Maganzini

Photo: Billy Bragg, 2018 (Bruce Baker via Wikimedia Commons)