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At this point, Billy Bragg is more than just a musician; he’s an institution. The past 15 years have seen him become an author, political commentator, and de facto curator/proselytizer of the Woody Guthrie legacy, in addition to his own musical output. Given his current status as a beloved, NPR-friendly raconteur in America and “national treasure” back in England, it’s hard to remember a time when Bragg was a divisive figure who invented his brand of scrappy folk-punk that was equal parts love songs and socialism. Bragg’s recent albums feature lots of the upbeat, soulful roots music that has increasingly dominated his records since 1996’s William Bloke. His early career, however, sounded much different.

Following the dissolution of his first band, Riff Raff, and a brief stint in the British Army, Bragg burst onto the scene as a solo musician with little more than his heavily accented voice and a slightly-distorted guitar on 1983’s mini-album, Life’s a Riot with Spy Vs. Spy, which set the template for his early work. The following year he released a proper full-length, Brewing Up with Billy Bragg, which added only occasional production touches to his stark guitar songs. He expanded his sound further on his “difficult third album”, Talking with the Taxman About Poetry, in 1986, which was his first top ten album in the UK.

Workers Playtime (1988) was his breakup album, which also saw Bragg finally cave in and bring drums into the mix. Finally, in 1991 he released his pop masterpiece, Don’t Try This at Home. Recorded with an all-star cast including members of the Smiths, R.E.M., and Kirsty MacColl, the record gave him his highest-charting single, got him on Late Night with David Letterman, and allowed him to tour the world with a full band in tow. It also marked the end of his early work, as he would take five years off from recording after Don’t Try This at Home and return to the studio a husband and father with new responsibilities and concerns.

In his career since then, Bragg has managed the difficult task of aging gracefully without betraying the spirit of his first records. But for most inveterate Bragg fans, it’s his early work that burns the brightest. It’s on these first records that he slashes and burns his way through the political and personal struggles of early adulthood with the passion and idealism of youth. Here then are the ten finest moments of Billy Bragg’s early work.

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10. “Sexuality” (Don’t Try This at Home, 1991)

Sex by the end of the Cold War was a frightening proposition. A decade of Reagan/Thatcher Puritanism, combined with the threat of AIDS and the homophobia it spawned, combined to make human er… relations yet another battleground with literally life-and-death consequences. Against this background, Bragg’s lead single from his pop extravaganza Don’t Try This at Home felt like a breath of fresh air. Co-written with Johnny Marr, the song’s breezy production, cheery backing chorus (featuring Kirsty MacColl) all helped underscore the lighthearted, sex-positive hit long before that phrase migrated out of the university and into popular conversation.

It was one of Bragg’s biggest singles and what’s amazing is how quintessentially Billy the song is, full of sardonic self-deprecation and even a reference to the Red Star Belgrade socialist football club. While lines like “Just because you’re gay / I won’t turn you away” or “Safe sex doesn’t mean no sex” may seem clunky and obvious in the era of Lady Gaga, they were revolutionary for the pop charts at the time. Plus, I’m sure that Gaga will never write a line as funny as “I feel a total jerk / Before your naked body of work” or deliver it with half of Bragg’s charm and insouciance.

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9. “The Saturday Boy” (Brewing Up with Billy Bragg, 1984)

From its first wistful chords, “The Saturday Boy” tugs at your heartstrings and evokes the bittersweet nostalgia we all feel remembering the naïveté of young love. Bragg’s storytelling is note-perfect (unlike his singing) as he reminisces about all the little details of first love. He recalls treasured afternoons when he was able to walk her home or steal a dance in the school cafeteria to the Delfonics’ “La La (Means I Love You)” with amazing reverence. One can’t help but wonder if this is the same girl he sings about putting on a pedestal in “A New England”.

Of course, as with all early Bragg, our hero is doomed to be unlucky in love, complaining that “In the end, it took me a dictionary / To find out the meaning of ‘unrequited'” while the girl runs off to cooler parties without him. Though the story is a sad one, it’s leavened with humor, pathos, and sweet innocence that’s perfectly captured by the Penny Lane trumpet that accompanies Bragg’s lonely guitar. “The Saturday Boy” is Bragg’s anthem to that shy, awkward kid that everyone was at some point growing up. Some nearly 20 years on, it still packs an emotional wallop.

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8. “Levi Stubbs’ Tears” (Talking with the Taxman About Poetry, 1986)

Although ’60s folk-rock and UK punk were the most obvious influences on Bragg’s early work, often under looked is his passion for Motown and American R&B. He picked up not just the soulfulness of the singing but also a keen sense of rhythm which he brought to his guitar playing, especially in his third album, Talking with the Taxman About Poetry. The homage is made more explicit in the album’s lead single, which name-checks the lead singer of the Four Tops along with Berry Gordy and Holland and Dozier.

In “Levi Stubbs’ Tears”, Bragg paints a bleak but empathetic picture of a woman who ran away from home as a teenager to marry a man not worthy of that word. Although he’s boorish and cruel, she would rather suffer his abuse than live alone. Echoey vocals and stark guitar mirror the woman’s isolation and it’s not until the song’s coda that the mood lightens. As Bragg starts singing about the greats of Motown he’s joined by light bongos and trumpet and the song lifts off. The only relief to her loneliness is the love songs of her youth. Although it’s one of his saddest tracks, “Levi Stubbs’ Tears” is also one of the most powerful. Bragg always had a knack for exposing the often-unseen trials and burdens that come with being a woman in modern society, and he never does it more skillfully or compassionately than in this song.

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7. “Between the Wars” (Between the Wars [EP], 1985)

Although Bragg made his name as a protest singer, he was always more a progressive patriot than a “burn down the system”-style anarchist. Released on an EP of the same name in 1985, “Between the Wars” was an anthemic vision of England that differed starkly from the laissez-faire capitalist future that Margaret Thatcher was seeking to impose at the time. “I kept the faith / And I kept voting”, Bragg sings with hopefulness and determination that would come to define his political songs, “not for the iron fist but for the helping hand / For theirs is a land with a wall all-around it / And mine is faith in my fellow man.”

The almost religious reverence he attaches to these political ideas is stirring and gives the song a weightiness that put it a notch above your more standard punk screed. Written in the midst of the massive arms buildup at the end of the Cold War, Bragg’s warnings against “skies, all dark with bombers” also scan as a chilling warning premonition of what the status quo might yield. “Between the Wars” was Bragg’s first Top 20 hit and landed him on Top of the Pops, where he famously eschewed the show’s lip-syncing policy and delivered a stirring live performance that forever cemented the song’s place in the Bragg canon.

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6. “Waiting for the Great Leap Forwards” (Workers Playtime, 1988)

​By the time he went into the studio to record his fourth album, Bragg had been a full-time musician for nearly half a decade. During that time he was constantly touring, writing, and organizing. After such a whirlwind existence, it was a time to pause, look at the state of his life and the state of the world in order to try and figure out what, if any, success his effort had brought. “Waiting for the Great Leap Forwards” was the result. The song starts macro, as Bragg looks at the world just before the end of the Cold War and muses presciently about “luxury’s disappointment” and warns (as one of Fidel Castro’s brothers, no less) that “the Third World is just around the corner”.

But after the first few verses, Bragg shifts his focus to the micro, singing about the nature of fame and the point of “mixing pop and politics”, with a few jabs at himself “basking in the light of the 15 fame-filled minutes with the fanzine writer” thrown in. Built around a loose-limbed guitar riff and a tinkling dance hall piano, “Great Leap Forwards” is a slow-building singalong as each verse throws another instrument into the mix until finally, the chorus rolls in like a cathartic wave. In the end, Bragg answers his doubts with feisty optimism in the justness of his cause. In the end, his message is as relevant to punk rock as to politics; “If no one out there understands / Then start your own revolution and cut out the middleman.” The not-so-secret point being that the only way to leap forwards is to stop waiting and jump.