Shane MacGowan: 15 Essential Songs

In one of the Pogues’ tenderest ballads, MacGowan sings, “I took shelter from a shower, and I stepped into your arms on a rainy night in Soho.” It’s a tribute to the love of his life, the one who stole his heart at a young age, who transformed his life for better and/or worse — and it’s never clear whether that love is a woman or whiskey. Probably both. It’s that ambiguity that made MacGowan one of Irish rock’s greatest poets, and he knew it, too, since this track originally came out on an EP snarkily titled Poguetry in Motion. As the melody lilts around and MacGowan toasts friends who fell into heaven and some who fell into hell, all of his great loves sort of melt together, and it doesn’t really matter, which is the point: “Now this song is nearly over, we may never find out what it means/Still there’s a light I hold before me, and you’re the measure of my dreams.” That “measure,” of course, is a jigger — both the kind that measures whiskey and the lady who dances in his dreams. —K.G.

Best Christmas song ever? The Pogues brought on the great vocalist Kirsty MacColl for this 1988 tune about a couple of Irish immigrants in New York who arrive with big dreams and end up with nothing to show for it but their hate for each other, for their wasted dreams, and for the boys of the NYPD choir still singing “Galway Bay.” MacGowan and MacColl have better chemistry than a shot and a beer after Christmas Eve mass, with MacColl (who died tragically in 2000) giving as good as she gets. When Shane calls her “an old slut on junk,” Kirsty rifles back with a homophobic slur that shocks by today’s standards: “You scumbag, you maggot/You cheap lousy faggot/Happy Christmas your ass/I pray god it’s our last.” (Jon Bon Jovi changed it to “braggart” when he rerecorded it in 2020). As the Sinatra strings swell around them, the hopelessness rips your heart out. And somehow this became an MTV hit. —J.D.

This rambunctious anthem is one of the best examples of Shane MacGowan’s ability to punk up Irish folk. Written by MacGowan as the title track of the Pogues’ third album, it addresses death, drowning, and maybe even some of Ireland’s politics. “This land was always ours/it was the proud land of our fathers,” he snarls in one verse before letting out a piercing scream. But it’s the “coming up threes” allusion that is most rich in imagery, of the maritime kind: Lore has it that before you drown, you surface three times. As MacGowan delivers it, in a chorus so hooky it was once used in a Subaru commercial, he’s at peace with the end result: “Let me go, boys.” —J.H.

Anticipating the upbeat, ultra-optimistic, everybody’s-in-this-together euphony of Britpop before Blur and Oasis had even formed, the Pogues’ “Yeah Yeah Yeah Yeah Yeah” was a feel-good bullet of good will (with a Top of the Pops-themed music video that also predated Nirvana’s “In Bloom”). The lyrics are one great big apology in which MacGowan admits he was a total jerk to the girl he liked since school (with some tawdry tangents), then promises to be the man she hopes he’d be with lots of positive affirmation: Yeah yeah yeah yeah yeah! “Now all that I can do is hope and pray that you’ll forgive me before it’s too late,” he sings. “There’s only one thing I can say to you, you know I’ll love you, you know it’s true.” It was the band’s first U.S. hit. (Don’t skip the “extended version” for extra yeahs.) Yeah! —K.G.

One of MacGowan’s great immigrant anthems, “The Sunnyside of the Street” bears one of his best choruses: “I saw that train and I got on it/With a heart full of hate and a lust for vomit/Now I’m walking on the sunnyside of the street.” When paired with Spider Stacy’s tin whistle melody and co-writer Jem Finer’s finest mandola playing, the song paints a realistic picture of the hope and anxiety of leaving your native land for something better. Thanks to expert production by the Clash’s Joe Strummer (who briefly replaced MacGowan when the Pogues kicked him out after this album), MacGowan’s growl rests gently in the sunnyside of the mix. “I knew that day, I was going to stay right where I am,” he sings. “… On the sunnyside of the street.” —K.G.

Could anyone growl “What a Wonderful World” as well as Louis Armstrong? No, but if anyone could come close to his guttural greatness, it was MacGowan, who recorded this rousing cover with Nick Cave in 1992, shortly after his ejection from the Pogues. In the music video, he closes his eyes (thinking to himself) and sort of melts into the lyrics as he and Cave shake hands during the “friends shaking hands” verse. It was an ironic vision of peace coming strangely from two of the era’s greatest hell-raisers. The song was a minor, wonderful hit in the U.K. that year. —K.G.

MacGowan might not appear to be a leading man, but on this melancholy duet with Sinéad O’Connor, which appeared on the soundtrack for 1995’s Two If By Sea, he steps effortlessly into that role. Offsetting the falsetto notes of O’Connor’s opening lines — “Do you remember that sunny day/somewhere in London in the middle of nowhere” — MacGowan’s gruff declarations of love give the song an endearing quality. The Pogues had recorded “Haunted” a decade earlier for the Sid and Nancy soundtrack, with MacGowan singing alongside Cait O’Riordan, but it was the chemistry between him and O’Connor that made the song a minor hit, reaching Number 30 on the U.K. charts. The two remained close friends, but in 2000 they had a falling out when O’Connor called the cops on MacGowan, hoping it would help him kick heroin. They eventually rekindled their friendship, but it’s this song — a ghostly ballad about enduring love — that will forever encapsulate their shared greatness. —E.G.P.

If anyone other than Frank Sinatra earned the right to sing this ode to willful stubbornness, it was MacGowan. By the mid-Nineties, when he turned the song into a Celtic-punk brawl, he was pushing 40 and had been through it. It all came out in his rendition, which was neither campy nor kitschy but a defiant statement of purpose. When he gargled, “Let the record show, I took all the blows/And did it my way,” he not only meant it; he was proud of it. MacGowan’s last shining moment, it naturally concludes with a touch of electrified Irish music, just to remind us where his roots lie. Somewhere, let’s hope he and Frank are tossing back a few together. —D.B.