It was at Christmas 1987 that The Pogues' "Fairytale of New York" first became a Christmas hit in both Ireland and the UK. Twenty years later it is still going strong when other Christmas songs have faded into obscurity. It is a weird and peculiarly evocative song. But what does it mean? In Wikipedia they say this:-
The song takes the form of a drunken man's Christmas Eve reverie about holidays past while sleeping off a binge in a New York City drunk tank. After an inebriated old man also incarcerated in the jail cell sings a passage from the Irish drinking ballad "The Rare Old Mountain Dew", the drunken man (MacGowan) begins to dream about a failed relationship. The remainder of the song (which may be an internal monologue) takes the form of a call and response between two Irish immigrants, lovers or ex-lovers, their youthful hopes crushed by alcoholism and drug addiction, reminiscing and bickering on Christmas Eve in New York City. The lyric "Sinatra was swinging" has been taken by some to suggest an unspecified period after World War II; however, it is possible that the song is actually set in the early 1980s, when one of Sinatra's last chart hits, his 1980 recording of John Kander and Fred Ebb's theme from the movie "New York, New York", was a fixture of New York City airwaves and a standard singalong record in the city's many neighbourhood bars. The title, taken from author J. P. Donleavy's novel "A Fairy Tale of New York", was chosen after the song had been written and recorded.
For me it is a song about lost dreams, regrets and underachievement. All of us have suffered the buffeting of life's roller coaster ride. We could have all "been someone", just as we could have all ended up in "the drunk tank" on Christmas Eve. Whenever I hear this song, I think of Kirsty MacColl who died so tragically and needlessly in Mexico eight or nine years ago and I think of her father Ewan and the subtle way his lyrical brilliance infiltrated Shane McGowan's masterpiece.