The Pogues – Boys from the County Hell (1984)
In his 2001 memoir, MacGowan expressed frustration about the production on the Pogues’ 1984 debut album, Red Roses for Me, lamenting that the “thunderous sound” of the band’s concerts didn’t translate into the studio. Luckily, Boys from the County Hell teeters on the right side of ramshackle, as the song’s racing tempo, lively tin whistle and accordion and duel-at-dawn banjo ambience create an aura of jaunty menace. Fittingly, MacGowan also turns in some of his best early lyrics featuring a tough gang of drunken hooligans that won’t hesitate to put a no-good landlord (or anyone else) in their place.
The Pogues – A Pair of Brown Eyes (1985)
MacGowan’s best songs come across like vibrant vignettes that illuminate larger human truths. The melancholy waltz A Pair of Brown Eyes features two strangers who meet in a bar and discover they have something painful in common: they’re haunted by an ex who had brown eyes. One man is a veteran who took solace in the thought of his lady’s brown eyes while being deployed, but discovered after he came home that his relationship was over. In turn, this tale of woe causes the other man to spiral into regret and sadness over his own lost, brown-eyed love. MacGowan’s no-holds-barred imagery (the veteran observed “the arms and legs of other men / were scattered all around”) places this pining in stark perspective.
The Pogues – Dirty Old Town (1985)
By putting a righteous modern spin on traditional and Irish folk music tunes, the Pogues ensured these songs remained relevant to younger generations. On Rum Sodomy & the Lash, MacGowan and co did quintessential versions of both And the Band Played Waltzing Matilda and Dirty Old Town. Written by folk icon Ewan MacColl, the latter is an anti-capitalism anthem hidden in a celebratory romantic ballad: the lyrics describe finding love in a hopeless place – a polluted, industry-heavy landscape that the narrator then wants to destroy. MacGowan is the perfect hero of the Pogues’ cover, as his rough-hewn vocals possess the requisite tenderness and moral integrity.
The Pogues – Sally MacLennane (1985)
Another highlight of Rum Sodomy & the Lash, Sally MacLennane is a brisk march that resembles the soundtrack of a raucous night out. Lyrically, MacGowan captures the sentimental aspects of a neighbourhood pub while seeming to comment on the ideas of death and the afterlife: the touching lines “We walked him to the station in the rain / We kissed him as we put him on the train” might evoke the day of a funeral. Sally MacLennane is based on regulars of a real-life pub overseen by MacGowan’s uncle that drew Irish workers at the Dagenham Ford plant. (The “elephant man” referenced is real, MacGowan swore.) The song describes the journey of a restless harmonica player named Jimmy, who leaves town to find his fortunes and then returns years later – only to meet an untimely demise while grieving his friends who died since he’s been gone.
The Pogues – A Rainy Night in Soho (1986)
Found on 1986’s Poguetry in Motion, A Rainy Night in Soho is MacGowan at his most meditative. Glittering strings, stately piano and genteel flugelhorn create an aura of sophistication that fits the subject matter. Depending on your perspective, A Rainy Night in Soho can be interpreted as an ode to a long-term love who provides emotional and physical solace – or an extended metaphor for the way alcohol can also be a seductive support system. Either way, it’s one of the Pogues’ most beautiful songs, a tune full of evocative imagery and sweet nostalgia: “On a rainy night in Soho / The wind was whistling all its charms.”
The Pogues – Fairytale of New York ft Kirsty MacColl (1987)
Hope springs eternal on one of the unlikeliest classic Christmas songs ever. Co-written by MacGowan and Jem Finer, Fairytale of New York features two denizens of a New York City drunk tank navigating their toxic co-dependent relationship: MacGowan’s louche, rakish drunk and Kirsty MacColl’s troubled drug user. Despite their intense life regrets and marked lifestyle differences, the couple still hear the beauty in the bells that are “ringing out on Christmas Day” – a sign that even life’s darkest moments contain glimmers of optimism. Accordingly, Fairytale of New York is all about musical subtlety: soft accordion drone, a sturdy piano melody, a lilting tin whistle and bittersweet strings.
The Pogues & the Dubliners – The Irish Rover (1987)
It wasn’t quite a passing of the torch when Irish folk legends the Dubliners collaborated with the Pogues on a barnstorming 1987 cover of classic tune The Irish Rover. After all, the Dubliners more than held their own on the track, which reached the UK Top 10 and topped Ireland’s singles chart. However, MacGowan especially sounds energised by the collaboration, chiming in with a spitfire vocal performance that adds snarled punk edge to the tune.
The Pogues – If I Should Fall from Grace With God (1988)
Propelled by galloping drums, nimble banjo and pogoing accordion, the title track of the Pogues’ 1988 album comes close to capturing the strident punk energy of the band’s live show. MacGowan leads the way, unleashing the occasional guttural scream in between his snotty vocal delivery. Lyrically, If I Should Fall from Grace With God depicts someone trying to grapple with the enormity of their mistakes in the afterlife – only to discover the redemption (and salvation) won’t come easy, if it comes at all.
Shane MacGowan and the Popes – That Woman’s Got Me Drinking (1994)
After MacGowan parted ways with the Pogues in the early 1990s, he formed Shane MacGowan and the Popes. Unsurprisingly given the name, the group continued down a similar roughshod path as the one traversed by MacGowan’s former band. Their debut album The Snake featured That Woman’s Got Me Drinking, a hip-shaking blues-punk number that finds a narrator driven to drink by their significant other. That doesn’t mean they’re leaving her, however: “If I had the guts to do it / I’d take the long goodbye / Instead I’ll love her long and hard / And love her ‘til I die.” Overindulging isn’t exactly the healthiest coping mechanism – but the song’s conflicted heart at least means well.
Shane MacGowan and the Popes with Sinéad O’Connor – Haunted (1994)
A subdued remake of a song originally done by the Pogues in 1986 for the Sid and Nancy soundtrack, the duet now seems extra poignant given that both MacGowan and O’Connor are gone. Both vocalists exude vulnerability in the way they frame eternal love (“I want to be haunted by the ghost / Of your precious love”), while O’Connor’s delicate, fragile tone is a perfect contrast to MacGowan’s gruff, tough-guy-with-a-tender-heart veneer.