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10 Of The Most Creative Christmas Songs Of All Time
Singer and Jazz musician Nat King Cole, 1942.
Smith Collection/Gado/Getty Images

Christmas music — the umbrella term for songs whose lyrics or motifs allude to the Christian holiday — is disregarded as pedestrian mall music, bereft of artistic merit. It is often pigeonholed into the same perfunctory and repetitive playlist as such novelty tunes as “Happy Birthday.” 

However, as an extensively broad genre, brimming with sundry musical styles, Christmas music comes packaged in many forms: swing, jazz, soul, rock, pop, and even orchestral. Moreover, Christmas music, just as Christmas movies, has its many misses and disposable clichés — 2004’s Christmas with the Kranks comes to mind — but it also has its brilliantly composed classics such as It’s a Wonderful Life (1946).

Wading through a sea of shameless cash grabs from artists whose insipid Christmas covers are only fit for department store playlists, I have collected and compiled a chronological list of Christmas songs that are disarmingly creative in their musical chic. 

Ella Fitzgerald – “Sleigh Ride,” Ella Wishes You a Swinging Christmas (1960)

If you’re going to listen to Christmas music staples, you may as well listen to the best versions of the Christmas classics. Nearly any track from Ella Fitzgerald’s 1960 classic Christmas record is a worthy contender for a spot on this list; but no song better captures Fitzgerald’s subtle, jazz-seasoned playfulness than “Sleigh Ride.” 

Prefacing the vocals is a festive horn section, frolicking up and down the scale, and underscoring the song’s seasonal mood. As Fitzgerald shortly descends into the mix, her voice exudes a sense of sincere joy and elation as she trades shots with the orchestra. It’s the sincerity in Ella’s voice that sets “Sleigh Ride” apart from reams of lesser recordings where the fun feels forced and lifeless. “Sleigh Ride” is a lighthearted, rollicking jazz-infused pop song that belongs on every holiday playlist.


Nat King Cole – “The Christmas Song,” The Nat King Cole Story (1961)

Perhaps no record arouses the aura of Christmas merriment as potently as Nat King Cole’s. It features jazz pianist Hank Jones, against the backdrop of a gorgeous, sweeping orchestral arrangement conducted by Ralph Carmichael. 

King Cole’s warm, velvet-like voice paints a canvas in plain sight; each syllable he sings layers a new coat, adding texture to the Christmas landscape: chestnuts roasting in the warmth of a rustic home, sheltering you from the biting cold chill outside.

Darlene Love – “Christmas (Baby Please Come Home),” A Christmas Gift for You from Philles Records (1963)

On “Christmas (Baby Please Come Home),” Darlene Love belts out the vocals and shimmies in and out of dazzling falsetto harmonies with smooth aplomb. Love makes you feel the lonely yearning in her voice as she howls the titular chorus line, “baby please come home.”  

Bestriding the day of the John F. Kennedy assassination, the record was initially withdrawn but has since remerged and enshrined itself in yuletide lore as a Christmastime classic. 

Vince Guaraldi Trio – “Christmas Time Is Here (Instrumental),” A Charlie Brown Christmas (1965)

American jazz pianist Vince Guaraldi always had a flare for innovation. He was an early importer of the Bossa nova beat to America, playing with Brazilian guitarist Bola Sete. It was along these inventive lines that Guaraldi came up with the novel idea to compose and play mellow jazz music in a children’s program: A Charlie Brown Christmas. 

On “Christmas Time Is Here,” Guaraldi’s melodic piano bars fall with the languid grace of snowflakes in the wintery air. The composition feels deceptively effortless; like a chess Grandmaster, Guaraldi plays and holds each note with sly precision; despite its simplicity, it’s far from simplistic. 

Otis Redding – “Merry Christmas Baby,” B-side to “White Christmas,” Atco Records (1968)

Demonstrating that Christmas music isn’t restricted to any single genre, Otis Redding’s “Merry Christmas Baby” is a soulful R&B number, replacing sleigh bells and chimes with electric guitar and bass. Redding’s band opens with a cyclic groove on the horns and a buttery-smooth bassline that extends through the whole song, driving the beat. Otis Redding delivers one of his most confident and blistering performances, blending his ability to comfortably howl at the peak of his vocal range (as on “I Can’t Get No Satisfaction”) with his immutable gospel influences. 

Joni Mitchell – “River,” Blue (1971)

If your aversion to holiday music stems from the overabundance of joy that permeates much of the genre, then Joni Mitchell’s “Blue” is your Christmas carol.  

Opening with the universally recognizable “Jingle Bells” chords, the song immediately nosedives into a blue haze of melancholy. Mitchell sings about being surrounded by happiness and joy when, internally, she is brimming with sorrow and grief. Unable to continue masking her anguish behind a façade, she is looking desperately to escape — wishing she had “a river to skate away on.” The terse arrangement — nothing but Mitchell and her piano — accentuates her environment; meanwhile, Mitchell’s shrewd songwriting ensures that despite its minimalism, her music never dulls. Instead, it captivates you, and makes you feel her sorrow.  

John Lennon – “Happy Xmas (War Is Over),” Single (1971)

Lennon’s “Happy Xmas” is a veritable Christmas rock song. Festooned with Phil Spector’s production frills and Nicky Hopkins’ dexterous touch on piano and chimes, “Happy Xmas” is a sonic delight that not even Yoko Ono’s out of tune singing could tarnish. 

Unlike Paul McCartney’s tacky and blithe gaiety on “Wonderful Christmastime,” Lennon’s holiday anthem feels earnest and sincere. The song largely jettisons the tried and true Christmas music formula of evoking jovial spirits. Instead, Lennon weaves a somber ballad that juxtaposes disparate vignettes: the upbeat aura of Christmas in America and the ongoing war in Vietnam. But it isn’t all gloom. Lennon offers respite, singing, “A very Merry Christmas, and a happy New Year; let’s hope it’s a good one, without any fear.” With the addition of the Harlem Community Choir on backing vocals, the record further elevates, gleaming like a gospel hymn. 

The Band – “Christmas Must Be Tonight,” Islands (1977)

Recorded in the final era of The Band’s original ensemble, “Christmas Must Be Tonight” was a welcome comeback for The Band after a brief low point induced by clashing egos and destructive vices. The last song on the A-Side of their final album Islands, “Christmas Must Be Tonight” succeeded in capturing all the elements that define The Band’s timeless sound.

Rick Danko’s earthy vocals, delivered in a calm and reserved cadence, are saturated with spades of emotion. In the chorus, Levon Helm harmonizes with Danko, channeling a feeling of camaraderie amongst the band that pervades their indelible anthems like “The Weight” or “The Night They Drove Old Dixie Down” — or from these same sessions, “Arcadian Driftwood.” Throughout all of this, Garth Hudson and Richard Manuel contour and candy the melody with tasteful fills on the organ and electric piano.

Robbie Robertson originally wrote “Christmas Must Be Tonight” for his newborn son, Sebastian. Much of the song’s lyrics are culled from scripture, harking back to the Biblical era: “How a little baby boy; bring the people so much joy; Son of a carpenter, Mary carried the light. This must be Christmas, must be tonight.”

Like most of The Band’s defining hits, “Christmas Must Be Tonight” transcends the era in which it was written and recorded. It doesn’t sound like anything put together by a troupe of 4 Canadians and an Arkansas native, but rather, it carries the traits of a hymn as old as the Bible, passed down through generations and sung for thousands of years. It’s an entirely original Christmas carol that undeservedly has never made it into the track list of a bestselling Christmas record or gotten the praise or attention it deserves.

Tom Waits – “Christmas Card from a Hooker in Minneapolis,” Blue Valentine (1978)

“Christmas Card from a Hooker in Minneapolis” is a bittersweet ballad for the downhearted. Tom Waits’ melancholy lyrics paint a bleak picture; they plant you firmly on a withered old barstool in a crummy dive, where the tack piano plays in the background as Waits’ growl reads to you a letter from a drug-addled prostitute from prison. As Tom Waits himself said, “I like beautiful melodies telling me terrible things.” For when you’re all worn out on the repetitive glee and merriment of “Jingle Bells,” there is no better antidote than this.

The Pogues – “Fairytale Of New York,” If I Should Fall from Grace with God (1987)

Another atypical Christmas themed song, “Fairytale of New York,” starts as a somber elegy: Pogues frontman Shane MacGowan ruminates on his bygone years, drunkenly singing overtop appropriately slurred piano chords. As he begins to muse about a lost lover, the tempo picks up. The orchestral arrangement widens with accordion and flute. Once Kirsty MacColl joins MacGowan on vocals, the song flowers into an upbeat, folksy Irish swing. The duo sling vocals back and forth in a call and response fashion as they reminisce their youth and the warm affection which they once shared for one another. “You were handsome!” MacColl exclaims, to which MacGowan ripostes, “You were pretty; Queen of New York City!” They blend their voices in the chorus, singing in unison “The boys of the NYPD choir, still singing Galway Bay; And the bells are ringing out for Christmas day.” 

Follow Harry Khachatrian on Twitter.

The views expressed in this opinion piece are the author’s own and do not necessarily represent those of The Daily Wire.

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