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Well, Merry Christmas folks and welcome to a special edition of the Chartcrush Top Ten Countdown Show! Normally on this show, we set our sights on a year in Pop history and culture and count down the top ten hits according to our exclusive rankings based on the weekly charts published in Billboard, the music industry’s top trade mag. Well this week, it’s still a top 10 countdown, and it’s still based on the Billboard charts, but instead of a year, we’re gonna home in on… Christmas music, which has never been bigger on the charts, with at least one Christmas song making the top 10 on the weekly Hot100 every Holiday season since 2017, and, every year since 2019, actually topping the chart!

Now it’d be totally wrong to conclude from that that Americans are listening to more Christmas music than in days gone by, but since on-demand streams on platforms like Spotify and Apple Music became the biggest factor in Billboard‘s weekly song rankings in the late ’10s, listening has been tracked and measured like never before, so it is safe to say that the charts are doing a better job of reflecting what people are listening to between Thanksgiving and New Years, and for that matter, all year. And yeah, people are listening to a lot of Christmas music!

So we’ve crunched the data, same as we do when we rank the songs for our year-focused episodes, and this hour, we’re gonna count ’em down: the top-charting Christmas songs so far in the streaming era, 2016 to 2023.

Now Christmas records have been making the charts since the first year there were charts, 1940, when the Glenn Miller Band’s jazzed-up “Jingle Bells” made Billboard‘s Best Sellers in Stores top 10 two weeks at Christmas.

In the War years it was Bing Crosby’s “White Christmas” starting in 1942 when it first came out, and it charted 18 of the next 20 Christmas seasons.

The late ’40s and early ’50s were sentimental, nostalgic times in America, and a golden age of Christmas music that produced many of the classic songs and performances still played at Holiday time by Singers like Nat King Cole, Gene Autry and Perry Como. Then Rock ‘n Roll changed everything on the charts, but not at Christmas! Like “White Christmas,” many pre-Rock era discs continued to chart year-after-year as Rockers and a new generation of Pop Singers added to the evolving canon.

The sole #1 Christmas hit of the ’50s decade, though, hasn’t aged very well. Sped-up vocals might’ve seemed like a marvel of modern studio-craft when The Chipmunks’ “Christmas Don’t Be Late” topped the chart in 1958, but it’s the highest-charting Christmas hit we won’t be hearing in our countdown—and that despite a new version charting over the holidays in 2007 after the Alvin & The Chipmunks movie hit theaters.

In the 1960s, Christmas music surged to new heights as Americans geared up at hi-fi shops, and in ’63, Billboard launched separate charts for it and removed holiday music from the Hot100 and the album charts. Those special holiday charts dwindled away to nothing, though, amid the revolutionary turmoil of the late ’60s, and Billboard discontinued them in 1973.

The first Christmas songs to chart on the Hot100 in ’73? John Denver’s “Please, Daddy (Don’t Get Drunk This Christmas)” and Merle Haggard’s equally desperate “If We Make It Through December.” Boy how times had changed! And Christmas music on the charts continued to be kind of a bummer straight through “Do They Know It’s Christmas?,” the 1984 New Wave charity guilt trip, ’til 1992, when David Letterman’s “Christmas Queen,” early ’60s Girl Group Singer Darlene Love, charted the first upbeat, positive holiday hit in 30 years, “All Alone on Christmas” from Home Alone 2. Lonely title; happy song, and backed by Bruce Springsteen’s E Street Band.

But despite that, and “Macarena Christmas” for ’96, it was gonna take generational change to finally dispense with Jonesers’ and X-ers’ cynicism about Christmas and Christmas music, and that came when Millennial Christina Aguilera scored the biggest Christmas hit on the Hot100 since “Do They Know It’s Christmas?” with her sincere remake of “The Christmas Song (Chestnuts Roasting on an Open Fire).” That got to #18, followed by Shedaisy’s “Deck the Halls” and the first chart appearance for Mariah Carey’s “All I Want for Christmas Is You” in 1999.

In the ’00s, Christmas music mostly lived on Adult Contemporary radio, but besides News and Talk, that was the top-rated format on radio, and once downloads and on-demand streams took over the Hot100’s ranking calculus, Millennials and Gen-Z had a clear shot at remaking Christmas in their own image. So what did they do? Well that’s what we’re gonna find out this hour here on our Chartcrush Christmas countdown of the top ten Christmas hits (so far) in the streaming era!

#10 Dean Martin – Let It Snow! Let It Snow! Let It Snow!

And #10 as we kick things off is a big hint. The song had been a #1 hit, not just before the streaming era, but before vinyl! Yeah, there was an era before vinyl, pre-1949 when brittle, delicate 78s were the only format for music, and the first Christmas after the Allied victory in World War 2, 1945, this song by Jule Styne and Sammy Cahn was #1 for five weeks for Boston area Bandleader/Singer Vaughn Monroe.

Monroe’s deep Baritone voice, though? Quite dated, and a hard sell even for sentimental Millennials and Gen-Zers, who preferred this version of the song in stereo, recorded for Dean Martin’s 1966 Christmas album (between drinks perhaps!). The #10 Christmas hit of the streaming era? Dean Martin’s version of “Let It Snow! Let It Snow! Let It Snow!”

Dean Martin, “Let It Snow! Let It Snow! Let It Snow!” #10 on our Chartcrush Christmas Special counting down the top ten Christmas hits so far in the streaming era, 2016 to 2023. Deano’s version never made the Hot100 when it first came out because, again, Billboard wasn’t charting holiday songs on the Hot100 in the ’60s, but also, it wasn’t released as a single. His version of “White Christmas” was the single from his 1966 Christmas album “Let It Snow” was on, and it didn’t chart.

But of all the versions of “Let It Snow” over the years—Bing Crosby, Frank Sinatra, Ella Fitzgerald, Rod Stewart, Jessica Simpson, Michael Buble and many others, including Vaughn Monroe, that original one—year-after-year since 2018, Deano’s version is the only one that’s made the charts.

Martin also charted over the 2019 holidays with his 1959 duet with Marilyn Maxwell on “Baby It’s Cold Outside“.

#9 José Feliciano – Feliz Navidad

At #9, a song written and recorded in 1970, which you’ll recall from the intro was a time when Christmas music was in a downward spiral. And the Singer/Songwriter never expected it to do anything at all; he just dashed it off in minutes one day, far from home in a studio in L.A., feeling homesick and nostalgic for his family Christmas in Puerto Rico. But over the years it gradually picked up steam and first charted Christmas 2016: the traditional Spanish Christmas and New Year greeting that translates to English “Merry Christmas, a prosperous year and happiness.” At #9, the first bilingual Christmas song, José Feliciano’s “Feliz Navidad.”

“Feliz Navidad, próspero año y felicidad.” That’s Spanish for “Merry Christmas, a prosperous year and happiness.” José Feliciano with the #9 Christmas song here on our special edition of Chartcrush counting down the top 10 Christmas hits of the streaming era based on Billboard‘s Hot100 rankings since 2016.

After charting at Christmas in 2016, it went missing from the charts at Christmas 2017, which is really ironic because 2017 was the year Luis Fonzi’s “Despacito” was #1 for 16 weeks: a watershed for Latin Pop. But “Feliz Navidad” was back in ’18, and every year since, first making the top 10 in 2020 and returning in ’21, ’22 and ’23.

#8 Wham! – Last Christmas

Next up at #8, something from the ’80s, when Christmas music still wasn’t very cool, but anything by this Act was gonna get attention. Besides, the song is less about Christmas than the heartbreak that inevitably results from misplaced emotions. Christmas is the backdrop, but also a motivator to do better. The cast of the TV show Glee first charted a version of the song in the U.S. off their 2009 Christmas album, and then up-and-coming Pop star Ariana Grande made the charts with her version at Christmas the year she debuted on the Hot100, 2013.

But the original had never charted in the U.S. It wasn’t released as a single despite getting to #2 on the U.K. chart upon its initial release in 1984 and several more years after. That changed, though, in 2016 when the Writer and original Singer unexpectedly died, at just 53, on Christmas Day. So in tribute, the original made the U.S. chart, peaking at #41. And it’s come back at Christmas every year since, in the top 10 every year since 2020. At #8 it’s the late George Michael’s Duo Wham! with “Last Christmas.”

“Last Christmas,” Wham! at #8 on our special Chartcrush countdown of the top ten Christmas hits of the streaming era.

#7 Bing Crosby – White Christmas

At #7, the record I mentioned in the intro that first charted all the way back in 1942. Together with the Singer’s nearly identical 1947 re-recording of it for the same label, Decca (because the original master was worn out from all the re-pressings), it has charted 24 Christmases and counting, by far the most of any record in our countdown. And it would be more if Billboard hadn’t stopped charting holiday hits on the Hot100 in the ’60s and early ’70s.

The original version recorded in 18 minutes in 1942 is out there if you look for it, but it’s the 1947 one that re-entered the Hot100 in 2018 for the first time since 1962, and has charted every Christmas since. 1947: that’s the oldest recording in our Christmas countdown, and not only that, it’s the oldest recording ever to chart on the Hot100 period! At #7, Bing Crosby’s “White Christmas.”

Bing Crosby’s “White Christmas” at #7 here on our special edition of the Chartcrush Countdown Show: the top 10 Christmas hits of the streaming era. Like many of the ’40s top tunes, from a movie musical: Holiday Inn, in which Bing co-starred with Fred Astaire. And it won legendary Songwriter Irving Berlin his only Best Song Oscar, which he presented at the Oscar ceremony… to himself, the only time that’s ever happened. “And the Oscar goes to… me!” He humbly accepted. Berlin, a Russian-Jewish immigrant writing the biggest Christmas hit of all time. Only in America, folks.

#6 Andy Williams – It’s the Most Wonderful Time of the Year

Fast forwarding now for our #6 hit to 1963, when Billboard‘s first annual Holiday music charts were all about this Singer. And in the 10-year history of those charts, ’63 to ’73, no album racked up more weeks at #1: nine all told. Our #6 song was on that album, but the label, Columbia, didn’t see fit to promote it, at least at first. Instead they went with his version of “White Christmas,” and that actually beat Bing Crosby’s in ’63.

When the album returned to #1 on the Holiday chart in ’64 and Columbia did issue the song as a promo 45, it failed to make the singles chart. But after decades of holiday department store commercials using it and the Singer’s Christmas specials on TV, by 2001 it was big enough to make ASCAP’s first annual ranking of the top 25 holiday songs most played on radio, and by 2010 was #4 on that list. It made its streaming era Hot100 debut Christmas 2015, and has cracked the top 10 every year since 2018. At #6, Andy Williams’ “It’s the Most Wonderful Time of the Year.”

In a 2023 round-up of the 100 best Christmas songs of all time, Billboard‘s Staff was tempted to assign Andy Williams’ “It’s the Most Wonderful Time of the Year” a “schmaltz factor” of 11 on a scale of one to 10. “The most schmaltziest schmaltz of them all…like Santa flew in on his sleigh from the North Pole and wrote the song himself,” unquote. But if the key feature of holiday music in the 21st century is Millennials and Zoomers embracing the sentimentality of the season instead of laughing at it like their parents did, then schmaltz sells!

That subjective Billboard staff ranking put it at #14; we have it at #6 on our Chartcrush ranking of the top 10 charting Christmas hits of the streaming era based solely on chart placements. Williams’ “Happy Holiday/The Holiday Season” has also made the Hot100 every Christmas since 2019.

#5 Nat King Cole – The Christmas Song (Merry Christmas to You)

Now I mentioned that Bing Crosby’s 1947 re-do of “White Christmas” is the oldest recording in our countdown. Well if the Singer’s original version of our #5 Christmas hit was the one making the Hot100 every holiday season since 2015, he’d have ‘ol Bing beat by a year.

1946, the year he first waxed it, and that was a year after Mel Tormé saw lyricist Robert Wells’ jotted-down lyrics on an oppressively hot Summer day, pre-air conditioning, and the two of them went to work, trying to “stay cool by thinking cool,” and they finished the song in less than an hour.

Tormé eventually recorded it himself, but he gave it to his friend to cut the first version with his Jazz Trio and a small string section, and that made the top 10 on both Billboard‘s DJ and Best-Sellers charts in ’46: his biggest hit up ’til then.

In 1953 after he’d become a superstar Pop Crooner with his #1’s “Mona Lisa” and “Too Young,” he re-did it with Nelson Riddle conducting a full orchestra, and then again in 1961 in stereo (and with a little extra gravel in his voice) with a different Conductor (Ralph Carmichael), but sticking with Riddle’s arrangement. That version charted in ’62 and is the one that’s been re-entering the Hot100 every Christmas since 2015. At #5 it’s Nat King Cole’s “The Christmas Song.”

“The Christmas Song (Chestnuts Roasting on an Open Fire),” #5 on our Chartcrush Countdown of the top charting Christmas hits of the streaming era. As I mentioned earlier, it was Christina Aguilera’s warm, sincere version of that song in 1999 peaking at #18 that turned the tide on over 30 years of “too cool for school” cynicism and mockery of traditional Christmas music, the top charting holiday hit since “Do They Know It’s Christmas?” in 1984. But Nat King Cole’s 1961 version is tops in the streaming era. His version of “Deck the Halls” has also charted four years running since 2020.

#4 Burl Ives – A Holly Jolly Christmas

And it’s back to the mid ’60s for #4, to the 1964 Rankin-Bass stop-motion Christmas special, Rudolph the Red-Nosed Reindeer that’s been a must-watch on TV every Christmas since. The Singer is the voice of the Narrator, Sam the Snowman, and the song is in the special, but it’s a slightly different version recorded separately by the Singer in ’64 that’s become the Christmas standard on radio, and since the 2016 holiday season, on the Billboard Hot100. It’s been in the top 10 every year since ’18. At #4, Burl Ives’ “Holly Jolly Christmas.”

Burl Ives made his name as a Folk Singer, went to Juilliard, got parts in Broadway shows in the ’30s and started charting hits in 1949. In 1950 he cooperated with the House Un-American Activities Committee and avoided the blacklist, but at the expense of his relationship with other Folkies like Pete Seeger, whose group The Weavers went from #1 on the charts to not even being able to play clubs almost overnight in the early ’50s (they eventually reconciled).

Ives won an Oscar in 1959 for his Supporting role in the epic Western Big Country, so at 55 when he did “Holly Jolly Christmas” and voiced Sam the Snowman in Rudolph the Red-Nosed Reindeer, he was entertainment royalty.

#3 Bobby Helms – Jingle Bell Rock

At #3, a song that the Singer recorded at least seven versions of between 1957 and 1983, all quite different, but unlike Nat King Cole with “The Christmas Song,” none of them besides the 1957 original on Decca with Nashville Guitarist Hank Garland connected. And that original was a hit as soon as it came out just months after he’d scored his first top 10, “My Special Angel” in November of ’57.

He was the latest in a succession of young Nashville Rockabilly sensations, so when he dropped his Christmas single, Dick Clark’s Teen Dance show American Bandstand had him on to do it and the record shot to #7 on Billboard‘s Best Sellers chart. Unfortunately though, after that his singles barely dented the charts, and if not for his Christmas song charting again in ’58, ’60, ’61 and ’62, and then after that on that segregated Holiday chart into the ’60s, he’d be just one of many Rockabilly one-hit wonders.

In 2015 the song re-entered the Hot100, and it’s made the top 10 every year since 2018. At #3, Bobby Helms, “Jingle Bell Rock.”

Bobby Helms’ “Jingle Bell Rock” at #3 on our special Chartcrush Top Ten Countdown of the biggest Christmas hits of the streaming era. The first glimmer of its enduring success into the new century? It’s reappearance in the Arnold Schwarzenegger and Sinbad comedy Jingle All the Way, which got it back on the Country chart for two weeks during the 1996 Christmas season.

#2 Brenda Lee – Rockin’ Around the Christmas Tree

Well we’re down to #2, a record whose chart success in the digital era goes back to 2013 when downloads were still the Hot100’s top component as well as radio airplay and YouTube views. It skipped 2014, but it’s charted every Christmas since, peaking at #2 four years straight, 2019 to ’22. And in 2023, it became the only other Christmas song besides our song up next at #1 to top the Hot100 in the streaming era. At #3 it’s Brenda Lee’s “Rockin’ Around the Christmas Tree.”

Brenda Lee was just 13 when she recorded and first released “Rockin’ Around the Christmas Tree” in 1958. She did it at the insistence of veteran Songwriter Johnny Marks, who’d also written “Rudolph the Red-Nosed Reindeer,” first a hit by Gene Autry in 1949, and who later also wrote “A Holly Jolly Christmas” in 1962, Burl Ives’ hit we heard at #4.

1960 was Brenda Lee’s breakthrough year on the charts, with four top 10s including the #1’s “I’m Sorry” and “I Want to Be Wanted,” so “Rockin’ Around the Christmas Tree” first charted at Christmas 1960, peaking at #14, then re-entered again in ’61 and ’62 and on that Christmas singles chart thereafter.

#1 Mariah Carey – All I Want for Christmas Is You

So what’s the #1 song on our special Chartcrush Top Ten Countdown of the biggest Christmas hits of the streaming era? Well if you’re a chart watcher, you probably know already just based on all the hype that’s accompanied its re-appearance on the Hot100 year-after-year, but for the rest of you out there, I already mentioned it in my brief thumbnail history of Christmas songs on the Billboard charts at the top of the show: a song written and recorded in 1994 and issued as the lead single from the Singer’s first Christmas album at the height of her fame.

But still, it didn’t chart until 1999, the year Millennials imprinted themselves on pop culture with MTV’s Total Request Live, Britney vs. Christina and the Boy Bands, ‘NSYNC and Backstreet Boys. Christina (as in Aguilera’s) unironic, sentimental reboot of “The Christmas Song” cracking the top 20 after her explosive debut earlier in the year began a cascade of similarly sincere, good-timey neo-Christmas anthems that included our #1 song’s first chart appearance.

It only got to #83 while her song “Thank God I Found You” was starting its run to #1, but it’s still noteworthy in that it hadn’t charted when first released, and Airplay and CD sales were the only way to make the charts in ’99. And again, Darlene Love notwithstanding, Christmas songs like this just didn’t become hits. It’d been that way for 30 years. The fact that the Singer was Gen-X’s top charting Pop star made it even more poignant, like a long-overdue generational surrender to the simple joys of Christmas, with prodding from the younger generation.

Here it is: the #1 Christmas song of the streaming era, Mariah Carey’s “All I Want for Christmas Is You.”

It has a definite ’60s groove, but it’s Mariah Carey and it’s a song written and recorded in the ’90s, not the ’60s, ’50s or ’40s. “All I Want for Christmas Is You,” the #1 Christmas song, not just on our Chartcrush ranking of the top holiday hits of the streaming era, but any such ranking you’re likely to find.

It’s hit #1 on the Hot100 every Christmas since 2019, which breaks all kinds of chart records, too many to even get into. Maybe Billboard was right in 1963 when they gave Christmas music its own chart and took it out of the Hot100. Songs like the ones we’ve heard this hour are in a separate class: precious, timeless, artifacts of Christmases past, still cherished in the present, if only for a few weeks every year, but their enduring magic continues to bedazzle new generations of fans, and dare we say, perhaps even help shape musical tastes the other 47 weeks of the year in the future.

You’ve been listening to a special edition of the Chartcrush Countdown Show: the top 10 biggest Christmas hits of the streaming era. Thank you for listening. I’ve been your host, the creator of Chartcrush, Christopher Verdesi, and I also want to wish you the merriest of Christmases and a happy, fulfilling New Year.

On our website at chartcrush.com you’ll find a written transcript of the show you just heard, plus all our other episodes, each counting down the top 10 hits of a different year with commentary. And you’ll also find links to stream our Chartcrush episodes online, and other fun and informative goodies. Again, the website: chartcrush.com, I hope you’ll visit. And I hope you’ll tune in again next week, same station and time, for another edition of Chartcrush. Merry Christmas, folks!

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