Q List: Shane MacGowan's Greatest Songs

The first single the Pogues ever released, “Dark Streets of London” served as a perfect introduction to MacGowan’s signature blend of warmth and darkness, with cheerfully nostalgic memories of aimless days wandering his adopted hometown suddenly nosediving into nightmarish recollections of his time in a mental hospital, receiving electroshock treatments amid “the drugged-up psychos with death in their eyes.” He would revisit his hardscrabble youth on later tracks like “The Old Main Drag” and “Boys from the County Hell,” but never with such a striking balance of wistfulness and terror. -- Andrew Barker

MacGowan’s affection for the revolutionary Irish playwright/poet Brendan Behan is evident throughout the Pogues’ debut, Red Roses for Me, which also includes a cover of his prison ballad "The Auld Triangle." MacGowan imagines him in better spirits here, both figuratively and literally, and while the song’s freewheeling celebration of out-of-control drinking takes on a starker edge in light of both Behan and MacGowan’s well-documented battles with alcoholism, there’s no denying its eternal infectiousness—it would typically serve as the opening number for the Pogues’ 21st century reunion concerts. -- A.B

While MacGowan’s literary instincts were evident in fits and starts on the group’s debut, they exploded into full color on this breakneck opening track from the Pogues’ second album, Rum, Sodomy & the Lash. Loosely inspired by the Ulster Cycle of Irish folklore, the song uses the great Gaelic hero Cuchulainn’s moment of tribulation as a starting point for a fever-dream vision involving turn-of-the-century Irish pop music, IRA rebels, wild nights in Spanish brothels, ill-fated church visits, and an anti-Semite who gets what’s coming to him. What’s not to like? -- A.B.

MacGowan’s first great ballad, “A Pair of Brown Eyes” takes an ingeniously oblique path to its lovelorn refrain, as we meet a heartbroken young man towards the end of a long afternoon in the pub, when he encounters an aged veteran who regales him with anecdotes of wartime trauma. Barely listening to the old man’s tales of death and dismemberment, the narrator only latches on to his passing mention of a long-lost lover’s brown eyes, which sends him spiraling as he remembers the pair of brown eyes that waited once for him. (The song’s dystopian music video was directed by Alex Cox, who went on to memorably cast the band in his film Straight to Hell, an experience that inspired one of their most atypical singles.) -- A.B.

Delivered as a straight-line narrative, this song from the 1986 EP Poguetry In Motion is a (perhaps) intentional expansion on John Lennon’s “In My Life.” But don’t be fooled by MacGowan’s world-weary delivery. Ruminating over portions of childhood that are bathed in blurry black and white, MacGowan is absolutely pure in his intentions that this is a love song for someone he grew up with. The passage of time, it appears, has only made that bond stronger. (In her announcement of MacGowan’s passing, the singer’s wife Victoria Mary Clarke quoted the song’s immortal closing line: “You’re the measure of my dreams.”) -- Amy Hughes

Perhaps MacGowan’s greatest lyrical achievement, this bittersweet epic is a masterful patchwork of straightforward storytelling and brilliantly subtle detail. Witness how much is packed into the opening verse, as the young narrator attends a funeral for “Big” Jim Dwyer, a first-generation Irish-American boxer who may or may not have been killed in war: the Cadillac (that great symbol of midcentury American wealth) parked conspicuously outside, the itinerant Irish youth plotting to steal it, the looming specter of the coffin inside, the children sneaking booze, the drab historical lectures giving way to drunken chaos as glasses keep getting refilled at the wake... The Pogues tackled the Irish immigrant experience multiple times in their discography (the Phil Chevron-written "Thousands Are Sailing" being another stellar highlight), but never were the tensions between Old World and New spotlighted in such vivid and heartbreaking fashion. -- A.B.

Originally written on commission for the soundtrack of Sid and Nancy and recorded by the Pogues with bassist Cait O’Riordan singing lead vocals, this track found new life when MacGowan chose to revisit the track in 1995, this time formatting it as a duet with Sinead O’Connor. The combination of MacGowan’s whiskey-soaked, tobacco-scarred vocals and O’Connor’s sweetness creates a musical odd-couple scenario that works precisely because they’re so sonically disparate. “It’s a sad song,” MacGowan told Irish talk show host Pat Kenny in 1995. “But it’s happy in a way, because they’re reunited somewhere else.” It was a touching remark even then, but after losing both O’Connor and MacGowan in the span of less than six months, it plays like a total gut punch now. -- Will Harris

The Pogues’ most rousing anthem, this lead-off title track from the group’s masterpiece If I Should Fall from Grace with God is an unambiguous ode to Irish independence, but it functions just as well as a universal rallying cry of resistance and resilience. It was improbably later used in a car commercial, and well, if lyrics like “Bury me at sea, where no murdered ghost can haunt me / If I rock upon the waves, no corpse can lie upon me” inspire you to buy a Subaru, who are we to argue? -- A.B.

You don’t have to look too hard to spot the influence of James Joyce on MacGowan’s work — witness the stray “K.M.R.I.A.” in “Transmetropolitan,” or the cheeky way the group snuck a picture of the writer into a band photo. But the gloriously vulgar “Bottle of Smoke” may be the singer’s most singularly Joycean song. Exploring the aftermath of a horse race in wonderfully earthy detail (“Bookies cursing, cars reversing, glasses steaming, vessels bursting”), the track could almost be the long-lost segue between “After the Race” and “Two Gallants” in Dubliners. (One imagines lines like “priests and maidens, drunk as pagans” would have met with James’ approval.) -- A.B.

A No. 2 UK hit when it was first released, this duet between MacGowan and the late Kirsty MacColl would come to all-but-define the Pogues’ legacy for future generations. Featuring one of MacGowan’s most transporting melodies and a woozy push-pull between unabashed romanticism and lewd insults (including two slurs that are regularly omitted from most modern covers), it’s now considered a Christmas standard, making periodic returns to the UK pop charts every December. MacGowan was none too pleased to see some of the song’s rougher edges sanded off as it entered the Yuletide canon, however, noting that the song’s narrator “is not supposed to be a nice person...she is just an authentic character and not all characters in songs or stories are supposed to be angels, or even decent and respectable.” -- A.B.

As a lifelong student of traditional folk songs, MacGowan understood that the greatest lullabies have more than a hint of darkness amidst all of the gentle reassurance. And he offers a perfect illustration in this positively gorgeous ballad from the Pogues’ third LP. “May the ghosts that howl round the house at night never keep you from your sleep / May they all sleep tight down in Hell tonight, or wherever they may be” -- in MacGowan’s hands, more comforting words have rarely been sung. -- A.B.

MacGowan’s final two albums with the Pogues were infamously difficult affairs, with the frontman’s increasing unreliability and declining songwriting output eventually leading to his expulsion from the group in 1991. But he still managed to produce several masterpieces in those years, particularly this ode to a demolished dog-racing track, the rubble of which sends the narrator on a Proustian journey through memory. -- A.B.

Regrouping from his ouster from the Pogues, MacGowan put together a soundalike backing band called the Popes, and finally returned to record shelves with 1994’s excellent solo debut The Snake. A clear album standout, “The Snake with Eyes of Garnet” consciously echoes “Streams of Whiskey” as MacGowan recounts a dreamed meeting with 19th century Irish poet James Clarence Mangan, who serves as the singer’s Virgil figure as he witnesses a public execution rife with religious and mythological significance. -- A.B.

A remorseful love song written for his longtime partner, “Victoria” sees MacGowan reckoning, not for the first time, with the mess he’s made of his life, resolving to “put my pipe aside and hit the road...to find my girl with green eyes.” The track is anything but dour, though, blessed with a rollicking guitar-forward arrangement and some of MacGowan’s most oddly endearing lyrical imagery. -- A.B.

To anyone who observed MacGowan’s rise from anarchic punk rock scenester to troubled rock star and finally to cult-hero elder statesman, the idea that one of his final credits as a songwriter would come via a love ballad for an animated children’s film sung by Gerard Butler might have seemed absurd. But squint just right, and you can see how the same mind that produced “Haunted” and “Fairytale” could have penned the lyrics for this perfectly sweet duet from How to Train Your Dragon 2. Until the end, MacGowan’s genius for translating archaic song forms into modern contexts remained as sharp as ever. -- A.B.