Billboard magazine’s listing of the top 100 Christmas songs of all time, selected by its staff members in 2024, is an interesting attempt to capture America’s holiday music preferences…and one that sets the stage for great debate.
Curiously, songwriters are barely mentioned, and “cover songs” are fully eligible. We’ll touch on these concerns as we move through some of the “highlights,” starting with No. 100. The focus is on songs “that are played on the radio.”
In this case, we’re zeroed in on the playlist from WMGV-FM: Magic 103.3 / 95.5, an adult contemporary station that is part of Curtis Media Group, based in New Bern, N.C.
No. 100: Trans-Siberian Orchestra – “Christmas Eve/Sarajevo 12/24” – 1996. Written by Paul O’Neill, Robert Kinkel and Jon Oliva.
“The biggest hit from Trans-Siberian Orchestra is a Christmas jam for everyone who’s more into headbanging than holly. Amalgamating elements of ‘God Rest Ye Merry Gentlemen’ and ‘Carol of the Bells,’ then blowing them up to arena-sized proportions with crashing drums and (expletive deleted) guitar, this one barrels through our speakers like a freight train of cheer every holiday season, and we’re always down to get onboard,” said Billboard’s Katie Bain.
“‘Christmas
Eve/Sarajevo 12/24’ is totally over the top in a way that’s totally unique to
the holiday season,” Bain added.
No. 97: Johnny Mathis – “The Sounds of Christmas” – 1963. Written by Jerry Livingston and Paul Francis Webster.
Joe
Lynch of billboard commented: “Johnny Mathis’ run of Christmas albums coincided
with the rise of rock on radio in the 1960s, but his fealty to traditional
vocal stylings put him on the outs with the ‘cool crowd’ of the Boomer
generation. A pity, since his buttery vibrato is every bit as warm and
heartening as a hot toddy after a long trek through a blizzard.”
No.
88: Willie Nelson – “Pretty Paper” – 1964. Written by Willie Nelson in 1963,
the song was first recorded by Roy Orbison, who turned it into a hit. (Nelson
recorded his own version of the song the following year.)
Billboard’s Thom Duffy remarked: “To a sweet country box-step rhythm, Nelson sings the holiday tale of a street vendor calling out to Christmas shoppers ‘hoping you won’t pass him by’ as he offers ‘pretty paper, pretty ribbons of blue’ to ‘wrap your presents to your darling from you.’”
“The
backstory of the song was revealed in a 2008 Nelson biography in which author
Joe Nick Patoski wrote that Nelson was inspired by a disabled man, who could
not walk, but sold paper and pencils outside a department store in Fort Worth,
Texas,” Duffy said.
No.
83: Dean Martin & Marilyn Maxwell – “Baby It’s Cold Outside” – 1949.
Written by Frank Loesser. “Dean Martin’s billowing vocals gently overlapping
with Marilyn Maxwell’s delicate tone make for a cozy-by-the-fire feel,” wrote
Billboard’s Neena Rouhani.
No.
80: Tony Bennett – “Winter Wonderland” – 1968. Written in 1934 by Felix Bernard
and Richard Bernhard Smith, the song was originally recorded by Richard Himber.
“Artists
spanning countless genres have tried their hand at ‘Winter Wonderland,’”
reported Billboard’s Josh Glicksman. “It’s Bennett’s jazzy rendition that
captures the song best, more than five decades later. It’s airy enough to
create the sensation of a pleasant stroll and saves its brightest moments until
the very end to make all the surrounding scenery sparkle.”
No.
78: Dolly Parton – “Hard Candy Christmas” – 1982. Written by Carol Hall for the
musical “The Best Little Whorehouse in Texas.”
“This
may be the only Christmas song set in a brothel,” wrote Billboard’s Melinda
Newman. “The wistful ballad, poignantly rendered by Parton, is more about
rising above one’s circumstances and desired new beginnings than the holidays,
especially when all Santa has in his bag is a few pieces of hard candy.”
“There’s a little melodrama to be sure, but when Parton sings ‘I’m barely getting through tomorrow, but still I won’t let sorrow bring me way down,’ it’s like an angel’s blessing promising a brighter day is coming,” Newman said.
No.
77: The Ronettes – “Sleigh Ride” – 1963. Written in 1948 by Leroy Anderson as
an instrumental, the song was first performed by the Boston Pops Orchestra,
with Arthur Fiedler conducting. Lyrics were added in 1950 by Mitchell Parish.
The
Ronettes recorded a cover of “Sleigh Ride” in 1963 for Phil Spector’s “A
Christmas Gift for You.” Members of the group at the time were Ronnie Greenfield,
Estelle Bennett and Nedra Talley.
Billboard’s Katie Anderson said: “This version of the holiday standard ‘Sleigh Ride’ has it all: a horse neighing, jingle bells, the clip-clopping of hooves…and best of all, The Ronettes’ ‘ring-a-ling-a-ling-a-ding-dong-ding’ backing vocals. Our cheeks are nice and rosy thanks to the song’s sped-up tempo – that horse is really moving!”
No.
76: Perry Como – “(There’s No Place Like) Home for the Holidays” – 1954.
Written by Robert Allen and Al Stillman.
The best-known recordings of “Home for the Holidays” were made by Perry Como, who recorded the song twice, both times accompanied by Mitchell Ayres’ Orchestra and the Ray Charles Singers.
“This is a fine example of American pop music in the decade between the end of World II and the arrival of rock’n’roll,” said Billboard’s Paul Grein. “It’s pure Americana, from the line about ‘homemade pumpkin pie’ to the recurring lines about motoring cross-country to spend time with loved ones.”
No.
67: Bing Crosby & The Andrews Sisters – “Mele Kalikimaka (Merry Christmas)”
– 1950. Written in 1949 by Robert Alex Anderson.
The
song sends “Merry Christmas greetings from Hawaii.” While Bing Crosby is a
legend in the music industry, the Andrews Sisters weren’t too shabby, either.
They were really sisters from Minneapolis, Minn.: LaVerne Sophia, Maxene Anglyn
and Patricia Marie. They charted pop records from 1938-55. Perhaps their most
memorable hit, from 1941, was “Boogie Woogie Bugle Boy.”
No.
66: Andy Williams – “Happy Holiday/The Holiday Season” – 1963. The classic
holiday song “Happy Holiday” was written in 1942 by Irving Berlin for the movie
“Holiday Inn,” where it was introduced by Bing Crosby.
Kay Thompson wrote “It’s the Holiday Season” in 1945 and performed the song herself. Later, she paired her song with Berlin’s to create the medley that was performed by Williams.
Billboard’s
Paul Grein cited “the swinging tempo and Williams’ spry vocal,” which makes
some lines memorable, such as: “Leave a peppermint stick for old St. Nick /
Hanging on the Christmas tree.”
No.
59: Whitney Houston – “Do You Hear What I Hear?” – 1987. Written in 1962 by
Gloria Shayne and Noël Regney, the song was originally performed by the Harry
Simeone Chorale.
Many
artists have covered the song, but if you’re looking for: “‘A voice as big as
the sea,’ then Whitney Houston is the right woman for the job,” said
Billboard’s Katie Anderson. “With Houston’s vocal delivery, it all works,
creating a spiritual experience even for the non-believers.”
No.
42: The Ronettes – “Frosty the Snowman” – 1963. Written in 1950 by Walter
“Jack” Rollins and Steve Nelson. The song was first recorded by Gene Autry and
the Cass County Boys.
“The
Ronettes gave ‘Frosty’ extra verve and attitude in 1963 when they recorded it
for Phil Spector’s legendary holiday album, ‘A Christmas Gift for You,’” wrote
Billboard’s Paul Grein.
No.
41: Carpenters – “Merry Christmas Darling” – 1970. Written by Richard Carpenter
with lyrics by Frank Pooler.
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“Karen
Carpenter’s vocals on ‘Merry Christmas Darling,’ as she longs for her loved one
who is away for Christmas and New Year’s Day, is pure, sublime perfection,”
said Billboard’s Melinda Newman. “She conveys the perfect mix of yearning,
sadness and hope since she knows, even though it’s unspoken, they will be
joyfully reunited after the holidays.”
“Leave it to the background singers to ‘bring on the schmaltzy cheese,’ such as the line ‘the logs on the fire fill me with desire,’ and turning ‘Christmasing’ into a verb. But they just add to the song’s dreamy reverie,” Newman wrote.
No.
39: Ella Fitzgerald – “Let It Snow! Let It Snow! Let It Snow!” – 1960. Written
by Sammy Cahn and Jule Styne in 1945, the song was first recorded by Vaughn
Monroe.
“It’s
Ella Fitzgerald’s brisk, jazzy 1960 version that’s proven to be the very
coziest,” commented Billboard’s Andrew Unterberger.
No.
31: Gene Autry – “Rudolph the Red-Nosed Reindeer” – 1949. Written by Johnny
Marks, the song is based on the 1939 story of the same name published by the
Montgomery Ward Company. Marks’ brother-in-law, Robert L. May, created the
character Rudolph as an assignment for the department store chain, and Marks
decided to adapt the story of Rudolph into a song.
It
was recorded by Gene Autry and soared to the top of the charts for the 1949
Christmas season.
“This tale of a bullied reindeer who becomes the story’s hero after leading Santa’s team through a foggy Christmas Eve thanks to his shiny red nose is an enduring classic,” remarked Billboard’s Jessica Nicholson. “It’s a relatable message for any child who has felt lonely and left out by other kids.”
No.
27: Paul McCartney – “Wonderful Christmastime” – 1979. McCartney wrote,
performed and produced “Wonderful Christmastime.” He played every instrument
himself – keyboards, synthesizers, guitars, bass, drums, percussion and jingle
bells.
Billboard’s
Joe Lynch thanked McCartney for giving the world a “light, joyous, seasonal
sing-along song” full of “charming ebullience. Its deceptive simplicity makes
it an evergreen delight.”
No.
26: Kelly Clarkson – “Underneath the Tree” – 2013. Written by Clarkson and Greg
Kurstin. The “Wrapped in Red” album is “an underrated holiday treasure, with
‘Underneath the Tree’ a shimmering diamond at its center,” wrote Billboard’s
Stephen Daw.
“The
boisterous big-band sound, optimistic lyrics and Clarkson’s unwavering vocals
made ‘Underneath the Tree’ an instant classic the moment it was released back
in 2013,” he said. “Clarkson’s performance is sentimental and filled with the
sort of Christmas cheer that gets us feeling all ooey-gooey around the
holidays.”
No.
25: Burl Ives – “A Holly Jolly Christmas” – 1964. Written in 1962 by Johnny
Marks, the tune was recorded in 1964 by The Quinto Sisters, a group of six
sisters (Lee, Bonnie, Chris, Elaine, Renee and Cindy), who had been discovered
by Mitch Miller.
The song was featured in the 1964 Rankin-Bass Christmas special, “Rudolph the Red-Nosed Reindeer,” in which Burl Ives voiced the narrator, Sam the Snowman. He was selected to sing “A Holly Jolly Christmas.”
“For
multiple generations, this boppy little jam is the sonic personification of the
entire holiday season,” commented Billboard’s Katie Bain. “Burl Ives
jingled-jangled it into ubiquity in 1964 with his velvet-voiced rendition.” The
song has “all the warmth, cheer and soothing innocence of Christmas baked right
into it. December hasn’t been the same since.”
No. 22: Eartha Kitt with Henri René and His Orchestra – “Santa Baby” – 1953.
Written by Joan Javits and Philip Springer, the song is a tongue-in-cheek look
at a Christmas list addressed to Santa Claus by a woman who wants extravagant
gifts such as a light blue convertible car, a yacht, personal checks from Santa
and decorations from Tiffany.
Music
critics gave mixed reviews to the single, with some calling it too suggestive
for a holiday-themed song.






















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