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White Christmas by Bing Crosby: More wistful than Good King Wencelas and less churchy than Away in a Manger, it’s the pop song that became a Christmas anthem. Penned by Irving Berlin, no less, the song won a Best Original Oscar when first crooned by Crosby in the 1942 film Holiday Inn. Twelve years and millions of records-sold later, the concept was reconfigured in the 1954 movie, which naturally starred Der Bingle and repeats ceaselessly this time of year. Can we even imagine the heartache this song evoked within military families during the Second World War?

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Happy Xmas (War is Over) by John Lennon: The late John Lennon wrote straight from the heart and he was still quite the angry young man when this song was released in 1971. In the vein of post-Beatles songs like Give Peace a Chance and Imagine, Lennon recriminates the listener with his soulful, if fantastically idealistic, hypothesis for global tolerance: “And so happy Christmas, for black and for white/For the yellow and red ones, let’s stop all the fights.” We should all probably be made to feel a little guilty this time of year.

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The Christmas Song by Nat King Cole: Known to most people as The Chestnuts Song, this song has been covered by everyone from Celine Dion to Justin Bieber, but the original take by Nat King Cole remains the definitive version. The smooth Mr. Cole languidly sells the slightly strange lyrics rambling on about Jack Frost and mistletoe and turkeys and tiny tots with glowing eyes and even the possibly-politically-incorrect line about “folks dressed up like Eskimos.” In fact, the song itself doesn’t make a lot of sense, but Nat’s smokey-voiced vibe just makes everything about the holidays sound so…desirable.

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Fairytale of New York by The Pogues and Kirsty MacColl: Still the preferred holiday song of misanthropes and college radio disc jockeys everywhere, this rousing 1987 ballad remains the best-known song by the Celtic-punk group The Pogues. In the best folk tradition, the rousing song tells of an Irish immigrant’s wretched Christmas Eve spent in the drunk tank of a New York jail. Pogues frontman Shane MacGowan trades bitter barbs (“You’re an old slut on junk”) with a disembodied lady love voiced briskly by MacColl, who gives back as good as she gets (including a homophobic slur). Great because not everyone loves Christmas.

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Christmas Wrapping by The Waitresses: Jaunty, jingly and full of New Wave holiday cheer, this 1981 song by The Waitresses is evidence that some white girls really can rap. The song’s narrative comes from lead vocalist Patty Donahue, who seems drolly determined to spend this Christmas by herself. Turns out she never managed to get together with the handsome guy she met the year before. But come Christmas Eve, she realizes she forgot to buy cranberries to go along with “the world’s smallest turkey,” so she races to the store where she bumps into Mister Right. Who doesn’t love a happy ending?

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Frosty the Snowman by The Ronettes: First recorded by the singing cowboy Gene Autry in 1950, this breezy story about an animated snowman with a corncob pipe and a button nose was much better served in 1963 by The Ronettes. Record producer Phil Spector’s famed “Wall of Sound” production actually makes the infantile lyrics seem incidental in the sexy Ronettes’ version, which has been used in the soundtrack of dozens of Hollywood films, most notably in Martin Scorsese’s Goodfellas as backdrop music for the scene in which Robert De Niro tears a strip off the dense wiseguy known as Johnny Roast Beef.

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Peace on Earth/Little Drummer Boy by David Bowie and Bing Crosby: Yes, Virginia, it’s possible for Christmas music to be both creepy and moving at the same time. Certainly it’s a tad unnerving that Crosby died four weeks after filming this duet with Bowie, which was for inclusion in the former’s 1977 holiday TV special. And it’s beyond obvious there’s minimal chemistry between the pair–they hardly look at each other throughout the song–but when their very distinct voices come together, it’s that rare merging of two musical universes.

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