The 50 Christmas songs you really will love (we promise)

Amy Winehouse, “I Saw Mommy Kissing Santa Claus”

Tommie Connor’s adorable novelty song—a kind of yuletide variation on the Freudian primal scene—was a No. 1 hit for tween singer Jimmy Boyd in 1952, but modern listeners know it better through the Ronettes’ full-throttle 1963 rendition on A Christmas Gift for You from Phil Spector. That’s the one that Amy Winehouse drew on for her own soulfully merry live version, in which Winehouse’s knowing vocals make it seem only natural that the song’s narrator take Mommy’s infidelity in such easy stride. Ho ho ho, indeed!—Adam Feldman

Watch the video for “I Saw Mommy Kissing Santa Claus” by Amy Winehouse

Stevie Wonder, “What Christmas Means to Me”

This much-covered Motown chestnut was written by Allen Story, Anna Gordy Gaye and George Gordy, but one of the things that made the young Stevie Wonder a miracle of American popular music was the way he invested descriptions of things he couldn’t have experienced firsthand—“Candles burning low / Lots of mistletoe / Lots of snow and ice / Everywhere we go”—with a breathless excitement and sweetness that make you a believer. (Compare with the versions by Jessica Simpson or Hanson for proof positive.)—Steve Smith

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Casiotone for the Painfully Alone, “Cold White Christmas”

The equivalent of a strangely beautiful lump of coal in your stocking, lo-fi luminary Owen Ashworth’s idea of a Christmas song is a muted yet wrenching portrait of postgraduation ennui, set against the backdrop of a particularly unfestive Midwestern winter. Anyone who’s ever felt conflicted about holiday-season homesickness will relate to the final line: “But you’ll be damned if you’re the one making collect calls / On a cold, white Christmas in St. Paul.”—Hank Shteamer

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Watch the video for “Cold White Christmas” by Casiotone for the Painfully Alone

Elton John, “Step Into Christmas”

Neither his most nuanced nor profound musical moment, this 1973 dazzler is Sir Elton at his silliest, most glittery best. “Welcome to my Christmas song!” he beams like a happy elf. If you can resist singing along to the chorus, you obviously don’t believe in fun. Like the big man says, “Step into Christmas: The admission’s free!”—Sophie Harris

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Otis Redding, “Merry Christmas Baby”

Otis Redding’s version of the original 1947 Johnny Moore classic “Merry Christmas Baby” is not so much a typical cheery Christmas jingle, but a sweet, soulful ode to his love. And why not? Christmas can be the most romantic time of the year; between Otis’s raspy vocals and the cheery melody, this little tune will have you serenading your significant other from start to finish.—Rachel J. Sonis

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Watch the video for “Merry Christmas Baby” by Otis Redding

The Dan Band, “I Wanna Rock U Hard This Xmas”

Nothing is sacred to Dan Finnerty and his shamelessly filthy, eponymous lounge act: not celluloid wedding scenes in Old School and The Hangover, and especially not Jesus’ birthday. The Dan Band’s Christmas ode arrives in the form of—what else?—an innuendo-stuffed power ballad, highlighted by lovable clunkers such as “I hope you like my present / It was way too big to wrap.”—Hank Shteamer

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The Pretenders, “2000 Miles”

Christmas is a time for getting together with loved ones, of course, but it can also be a stinging reminder of those friends and family members we can’t meet up with—a sentiment this early ’80s single captures beautifully. Listeners speculate that singer Chrissie Hynde penned “2000 Miles” about late Pretenders guitarist James Honeyman-Scott. Whatever the subject, the shimmering guitar-pickings and Hynde’s references to the holiday create a sweet-yet-mournful vibe we can all relate to.—Tim Lowery

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Watch the video for “2000 Miles” by The Pretenders

Kanye West, “Christmas in Harlem”

A sequel to Run-D.M.C.’s ’90s rap smash “Christmas in Hollis” (see No. 6), Yeezy’s “Christmas in Harlem” is a yuletide classic for the modern age. Featuring an army of hip-hop heavyweights like Jim Jones, Pusha T, CyHi Da Prynce and Harlem R&B soulstress Teyana Taylor, “Christmas in Harlem” is as hopeful as it is wistful. Mastermind producer Hit-Boy smartly mixes samples from “Strawberry Letter 23” by funk duo Brothers Johnson with “Mercy Mercy Me” and “Ain’t Nothing Like the Real Thing” by soul king Marvin Gaye to create a sense of warmth and coziness just in time for the Noel season. It also might be one of the very few Kanye tracks that seems, well, happy. It’s good to know that the holidays can lift anyone’s spirits.—Rachel J. Sonis

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Watch the video for “Christmas in Harlem” by Kanye West

Johnny Cash, “I Heard the Bells on Christmas Day”

Henry Wadsworth Longfellow wrote his poem “I Heard the Bells on Christmas Day” in 1863, inspired by his wife’s death and his son joining the Union Army without forewarning. In 1872, John Baptiste Calkin, an English church organist, paired the words with a melody he’d written years before. Hearing the almost nihilistic emotion, reckless faith and homespun tune all at once, you’d swear Longfellow and Calkin knew the Man in Black would make their song a hit in 1963.—Steve Smith

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Watch the video for “I Heard the Bells on Christmas Day” by Johnny Cash

Chuck Berry, “Run Rudolph Run”

We know what you’re thinking: “It’s about time Rudolph got his slot in this playlist.” Fret not; he’s too lovable to be shut out in the cold, and what better way to include ol’ Red Nose than with Chuck Berry’s 1958 version of “Run Rudolph Run”? No doubt this track will have you boppin’, hand jivin’ and swingin’ throughout the house with your loved ones right before Christmas madness ensues.—Rachel J. Sonis

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Watch the video for “Run Rudolph Run” by Chuck Berry