This Is Christmas, Song by Song

The Stories Behind 100 Holiday Hits


By Annie Zaleski

Illustrated by Darling Clementine

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Celebrate the merriest season of the year with award-winning author and music journalist Annie Zaleski's collection of the 100 most popular and beloved holiday songs of all time.

'Tis the season! Break out the eggnog, hang the mistletoe, blast those Christmas songs, and settle down in your favorite armchair with this beautifully illustrated volume exploring well-known and lesser-known behind-the-scenes stories of the 100 most cherished holiday songs of all time and their everlasting impact. From artists such as Bing Crosby and Ella Fitzgerald all the way up to Mariah Carey and Ariana Grande, this all-encompassing collection of holiday favorites is sure to warm your heart during the merriest season of the year. 

What song was listed in the Guinness Book of World Records as the best-selling single of all time? Which popular Christmas tune was reportedly written to commemorate Thanksgiving? What holiday song led to a special meet-and-greet between the song's 10-year-old singer and a 700-pound hippopotamus? 
Spanning musical genres and decades of classics and modern hits, some of the featured songs include:
  • “White Christmas” by Bing Crosby
  • "All I Want for Christmas Is You" by Mariah Carey
  • "Deck the Halls" by Mannheim Steamroller
  • “Christmas Tree Farm” by Taylor Swift 
  • “Christmas Time (Is Here Again)" by The Beatles
  • “Feliz Navidad” by José Feliciano 
  • "Rudolph the Red-Nosed Reindeer" by Gene Autry
  • "You Make It Feel Like Christmas" by Gwen Stefani
  • “Santa Baby” by Eartha Kitt
  • “Rockin’ around the Christmas Tree” by Brenda Lee
  • “Merry Christmas, Happy Holidays” by NSYNC
  • “Run Rudolph Run” by Chuck Berry
And many more!

Including full-color illustrations throughout, this gorgeously packaged compendium is the perfect gift for you and your loved ones to experience the holiday magic year after year. 



When you think of Christmas music, what comes to mind? Chances are good it’s mentions of snow, mistletoe, presents, Santa Claus, and decking the halls—or it’s the soothing sound of sleigh bells or jingle bells, shaking ever so lightly in the background. Maybe holiday songs symbolize the warm, fuzzy feelings of family together time, the carefree whimsy of childhood, or the kind of cozy romance that gets your heart pumping. Perhaps it’s the way Christmas tunes can provide a moment of solemn reflection—or, alternately, they might function instead as a silly, lighthearted escape from holiday stress.

In other words, Christmas songs are much more eclectic—and offer quite a bit more emotional depth—than you might initially think. Perhaps unsurprisingly, the history of Christmas music mirrors the history of popular music. Orchestras, jazz musicians, and big bands played festive tunes in the 1930s and 1940s, while the emergence of rock ’n’ roll in the 1950s injected some guitar-driven pep into Christmas music’s step. Once the Beatles shook up popular culture, that opened the door for holiday music across all genres—soft rock, soul, glam, punk, R&B, and synth-pop—to add pizzazz to the usual throwback Christmas classics and retro-cool standards.

Over the years, Christmas tunes have also often reflected contemporary history and culture. This can be positive—Elton John recorded 1973’s “Step into Christmas” at the end of a triumphant year full of chart success—or sobering. During World War II, Bing Crosby’s “White Christmas” and “I’ll Be Home for Christmas” resonated with soldiers and their families navigating challenging wartime separations, while the 1984 charity single “Do They Know It’s Christmas?” raised funds to benefit people affected by famine in Ethiopia. The subtext around the clandestine smooching in “I Saw Mommy Kissing Santa Claus,” meanwhile, raised some eyebrows and even led to the song being banned in a few places.

Christmas music can also ebb and flow in popularity. Sometimes that’s thanks to movie placements—just ask Brenda Lee about the positive impact from “Rockin’ Around the Christmas Tree” appearing in 1990’s Home Alone—or simply changing times. Producer Phil Spector’s 2009 murder conviction overshadowed his earlier work and career, including the seminal LP A Christmas Gift for You from Phil Spector, while “Baby, It’s Cold Outside” has drawn criticism in this modern age. Other songs have become extremely polarizing for reasons that are difficult to pinpoint—like Paul McCartney’s synthesizer-driven “Wonderful Christmastime.”

At the end of the day, Christmas music is deeply fascinating and illuminates greater truths about us and our world. This Is Christmas, Song by Song delves into the stories behind the 100 most meaningful Christmas songs of all time—the weird, the surprising, the touching, the festive. Some of these songs have straightforward origin stories; others have convoluted (or even exaggerated) histories. Oddly, many of them were written during the dog days of summer, when Christmas was still months away, and not as many as you might think have religious roots or are considered traditional songs.

These 100 songs are arranged in chronological order by year of release. That’s because ranking them by quality is just too difficult—and this method makes the evolution of Christmas music that much more prominent. Yet if there’s one thing all 100 songs have in common, it’s that they’re all part of a celebratory holiday season. So grab a candy cane (or two), throw on your best Christmas music mix, and please enjoy.



Songwriter: Traditional; modern version by Frederic Austin
Also covered by: Bing Crosby & the Andrews Sisters, Bob & Doug McKenzie, the Muppets and John Denver, Twisted Sister

WHAT’S BETTER THAN receiving presents from a loved one on Christmas morning? How about presents from a loved one for 12 straight days during the Christmas season? That’s the premise of the traditional song “Twelve Days of Christmas.” These gifts range in scope and size—geese laying eggs, a handful of gold rings, ladies milking, drummers—although the haul always ends with a lone partridge perched in a pear tree. (Say that five times fast!)

The 12 days of Christmas are a real holiday commemorated by Christians to celebrate the birth of Jesus. However, the basic framework of the song and its giving theme originated in a 1780 children’s book called Mirth without Mischief. Over the subsequent centuries, the words evolved and shifted as other writers interpreted and passed down the story.

At the start of the 20th century, the English composer Frederic Austin—who also restored the score for The Beggar’s Opera—drew on the earliest version of the words and developed a melody for them. He copyrighted the resulting song, “Twelve Days of Christmas,” in 1909, after having played it live for a few years before. In a footnote of a later reprint of the song, Austin noted, “This song was, in my childhood, current in my family. I have not met with the tune of it elsewhere, nor with the particular version of the words, and have, in this setting, recorded both to the best of my recollection.”

Austin’s version was well-received. A 1909 review in the Manchester Courier and Lancashire General Advertiser described it as “effectively arranged” even if “both words and music are more curious than beautiful.” That year, Austin’s new composition was also performed live, including at a December concert in Leicester, England, where it was described as a “seasonal novelty in the shape of a traditional air.”

The “Twelve Days of Christmas” has been redone in a humorous way, as Bob Rivers did with the “12 Pains of Christmas” (among other gifts: a hangover), and also in a straightforward manner by dozens of artists. Although in the modern world we might not welcome some of the gifts—swans aren’t necessarily very practical and they’re expensive—the generous sentiment at the song’s core stands.



Songwriter: Irving Berlin
Also covered by: Michael Bublé, Frank Sinatra, Meghan Trainor featuring Seth MacFarlane, Andy Williams

THE HOLIDAYS ARE supposed to be cheerful and carefree, a time to break bread and be merry with loved ones. But what if there’s a holiday season when joy is in short supply?

That’s the scenario posed by “White Christmas,” which became a hit as World War II intensified during the fall and winter of 1942. Written by Irving Berlin and performed by Bing Crosby, the song leans into holiday sadness. The narrator becomes deeply nostalgic while writing out Christmas cards, as it’s strongly suggested that the good tidings in the greetings are at odds with reality. In fact, the narrator pins their hopes and dreams on the possibility of a snow-filled Christmas, as that bit of whimsy represents not just a postcard-pretty setting but also simpler days and happier times.

Berlin started sketching out the song in January 1940, bringing an early draft into his office bright and early on a Monday morning. “Not only is it the best song I ever wrote, it’s the best song anybody ever wrote,” he reportedly said to his secretary, as noted in the book White Christmas: The Story of an American Song. However, Berlin had been ruminating on a song called “White Christmas” for a few years. A tune by the same name, but with a less somber vibe, appeared in 1938 as part of a never-produced Berlin show called The Crystal Ball.

Nevertheless, Berlin finally dug in and finished the circa-1940 “White Christmas” for the 1942 movie Holiday Inn, which costarred Crosby and Fred Astaire. Anticipation for the film began building almost a year in advance. Newspaper articles from 1941 touted that Holiday Inn had the most original music ever used in a film and teased the movie’s holiday-filled musical premise.

Buzz also started gathering around “White Christmas” specifically during the 1941 holiday season. In December, right after the attack on Pearl Harbor prompted the US to enter World War II, “White Christmas” was one of several Crosby holiday songs flown to England on a bomber airplane, at the behest of the British government. On Christmas 1941, Crosby also played the song on his NBC radio show, The Kraft Music Hall. A scratchy recording of this broadcast on acetate disk is solemn and aching, matching the national mood at the time.

Crosby was the perfect vocalist to deliver such a reassuring message. His delivery is sonorous and deeply empathetic. It’s not just aspirational listening to him croon lines about bygone perfect Christmases with pristine snow, children on their best behavior for Santa, and actual time to send handwritten cards. When the song ends, listeners truly believe they can achieve such an idyllic Christmas once again, whether very soon or in the future.

In the lead-up to the 1942 release of Holiday Inn, Crosby rerecorded “White Christmas” for Decca Records on May 29 at LA’s Radio Recorders studio. This new version is as reassuring and welcoming as the older take. On the recording is John Scott Trotter and His Orchestra—which contributes restrained, longing-filled strings, twinkling percussion, and velvety horns—and the Ken Darby Singers. The latter is a somber, coed choir that enters the song’s mix gradually. At times, they join forces with Crosby, while at other times they take the vocal lead. The net effect is that “White Christmas” makes listeners feel like they’re not alone in feeling blue—in fact, there’s a whole chorus of people ready to offer solace.

This version of “White Christmas” became a sensation when it was released, spending 11 weeks at No. 1 on the National Best-Selling Retail Records chart beginning the week of Halloween 1942. The song also topped charts again each year between 1945 and 1947. Crosby rerecorded the song again in 1947, faithfully re-creating the “White Christmas” magic.

The song is still listed in the Guinness Book of World Records as the best-selling single of all time, with a staggering 50 million copies sold, although its movie roots weren’t forgotten: “White Christmas” won an Oscar for Best Original Song, and Crosby starred in a 1954 remake of Holiday Inn, called White Christmas. To this day, the single is a staple of the holiday music season, telegraphing comfort to anyone who isn’t feeling festive.



Songwriters: Kim Gannon, Walter Kent, Samuel “Buck” Ram
Also covered by: The Carpenters, Kelly Clarkson, Johnny Mathis, Elvis Presley

BING CROSBY BEGAN 1943 on top of the entertainment world. Two films in which he costarred, Holiday Inn and Road to Morocco, made the list of top-grossing films of 1942. His single “White Christmas,” meanwhile, was finishing out an 11-week run atop the National Best-Selling Retail Records chart and had become an instant holiday classic.

However, in the real world, things weren’t quite as rosy. World War II was raging across Europe and the Pacific and wartime anxiety and stress were running high, as families dealt with separation from loved ones, food rations, and plenty of uncertainty. Enter Crosby’s 1943 contribution to the holiday canon, “I’ll Be Home for Christmas,” which captured the longing and sorrow of this fraught time. Simple yet effective, the song features a narrator who equates the holiday with small pleasures—snow, presents, and mistletoe—and tries to be reassuring about their chances of being home for the holidays.

If this sounds like the nostalgic scene Crosby described in “White Christmas,” that’s not entirely off base, as the two songs do have obvious parallels. “I’ll Be Home for Christmas” also features sparkling accompaniment from John Scott Trotter and His Orchestra, while Crosby’s vocal delivery here once again possesses both empathy and authority. Newspapers also naturally compared the two songs, with the Minneapolis Star noting, “This year’s ditty has the same sentimental appeal.”

However, “I’ll Be Home for Christmas” is decidedly less optimistic than “White Christmas,” with lyrics hinting that coming home for the holidays is sadly just a fantasy. The song’s title underlines this bad news, as it’s sometimes rendered with the parenthetical “If Only in My Dreams.” On another version of the song, Crosby is also joined by a chorus of male and female voices as the song progresses. The nod to wartime sorrows is impossible to miss: The men sound solemn as they sing lines about being home for Christmas, while women chime in on the lyrics about promising to have snow and gifts waiting.

The original 10-inch shellac single issued on Decca Records credited the song to Walter Kent and Kim Gannon; the duo worked as an architect and lawyer, respectively, before forming a songwriting team. However, Samuel “Buck” Ram—who would later find fame as the producer of the Platters—soon also earned a songwriting credit after a bout of litigation.

According to the Library of Congress, Ram copyrighted a song called “I’ll Be Home for Christmas (Tho’ Just in Memory)” in 1942. Billboard reported at the time that Ram had apparently shared this song with Walter Kent and even discussed a potential collaboration that didn’t pan out. However, when the Kent-Gannon composition “I’ll Be Home for Christmas” emerged in 1943, Ram’s publisher wasn’t thrilled and filed a copyright infringement lawsuit. The suit was settled within weeks, Billboard noted; among other settlement terms, Ram was added as one of the songwriters.

Despite the controversy, “I’ll Be Home for Christmas” ended up becoming a holiday favorite in 1943, peaking at No. 3 on Billboard’s National Best-Selling Retail Records chart. The song was covered countless times in the subsequent decades, as its sorrowful tone resonated with anyone who was missing relatives during the Christmas season. In a sign of its universal nature, “I’ll Be Home for Christmas” also eventually grew to become a touchstone for all kinds of homecomings. Most notably, in December 1965, when astronauts Frank Borman and James Lovell were winding down a then-record 330 hours in space on Gemini 7, the song was chosen to usher them back to Earth.



Songwriters: Ralph Blane and Hugh Martin
Also covered by: Christina Aguilera, Tori Amos, Michael Bublé, Frank Sinatra

JUDY GARLAND STARTED dabbling in more grown-up musical fare after her star-making role in The Wizard of Oz. In the 1944 MGM film Meet Me in St. Louis, which details the whirlwind lives of the Smith family of St. Louis, she portrays the second-oldest daughter, Esther. The role gave her the chance to record soon-to-be-classics “The Trolley Song”—which was nominated for an Oscar—“The Boy Next Door” and “Have Yourself a Merry Little Christmas.” Garland sings the latter tune to her on-screen sister Tootie (Margaret O’Brien) during a pivotal moment when the Smith family plans on leaving their Missouri home for New York City. The song is meant to be comforting, to relay that even if life separates us from friends and loved ones, the goodbye isn’t forever—just temporary.

These three songs are credited to the songwriting team of Ralph Blane and Hugh Martin, who sang together in a vocal quartet and later wrote for movies and musicals. According to a 1989 NPR interview, “Have Yourself a Merry Little Christmas” almost didn’t happen. “I found a little madrigal-like tune that I liked but couldn’t make work,” Martin said then, “so I played with it for two or three days and then threw it in the wastebasket.” Blane, however, assured his partner the song was good—and encouraged him to fish the song out of the trash. (In his 2010 memoir Hugh Martin: The Boy Next Door, Martin raised questions about the provenance of “Have Yourself a Merry Little Christmas” and other music from Meet Me in St. Louis; Blane, he claimed, didn’t write the music or lyrics to these songs and other compositions credited to the pair.)

There were initially other issues with “Have Yourself a Merry Little Christmas,” Martin recalled—namely that Garland and the movie’s producers thought the song was too much of a downer. At first, he also wasn’t keen on making changes. “[Garland] said, ‘If I sing that, little Margaret will cry and they’ll think I’m a monster,’” Martin recalled to NPR in 2006. “So I was young then and kind of arrogant, and I said, ‘Well, I’m sorry you don’t like it, Judy, but that’s the way it is, and I don’t really want to write a new lyric.’”

He eventually acquiesced to these requests, although any changes didn’t diminish the emotional ache at the center of “Have Yourself a Merry Little Christmas.” Garland’s vocal delivery is reassuring and heartfelt, while also being wholly sympathetic to her sister’s sorrow. Although she’s the older sibling attempting to keep a stiff upper lip, she lets her own grief and sadness slip through, making her performance that much more relatable.

Garland’s “Have Yourself a Merry Little Christmas” eventually performed modestly on the charts. Over the years, however, other takes on the song have become more common. Frank Sinatra covered the song on his 1957 LP A Jolly Christmas from Frank Sinatra and released the song again in 1963. The version from 1957 is crisp and resigned, with grandeur that comes from a cooing choir and a lush orchestra. And in 2022, Michael Bublé’s equally debonair cover of the song even charted on the Billboard Hot 100.



Songwriters: Mel Tormé and Robert Wells
Also covered by: Christina Aguilera, Jacob Collier, Perry Como, Mel Tormé

THE MOST MEMORABLE Christmases often don’t involve grand gestures. Instead, over time, you’ll fondly remember the way beloved annual traditions add up and result in an unforgettable holiday. On “The Christmas Song,” Mel Tormé and his writing partner Robert Wells vividly capture Christmas coziness—a chilly wind, a jolly choir, tasty roasted chestnuts—as well as the excitement of kids waiting for Santa Claus. The tune’s denouement is just as sweet: The narrator sincerely wishes everyone, young and old, a merry Christmas.

The songwriters penned the tune on an “excessively hot afternoon” in July 1945, Tormé recalled in his autobiography, It Wasn’t All Velvet


  • “Zaleski’s prose is crisp and informative and the page layouts are sprinkled with whimsical illustrations by Darling Clementine. An excellent choice for public library collections.”—Booklist
  • "The eclectic mix of pop standards, songs from TV specials, contemporary hits from Mariah Carey and Taylor Swift, and lesser-known punk and heavy metal Christmas tunes makes this an essential read for trivia buffs, music enthusiasts, and holiday revelers."—Library Journal

On Sale
Oct 17, 2023
Page Count
224 pages
Running Press

Playlist: This is Christmas, Song by Song

Annie Zaleski

About the Author

Annie Zaleski is an author, editor, and journalist with a focus on music and pop culture. Her work has appeared in dozens of publications, including NPR Music, The Guardian, Time, Rolling Stone, Salon, Billboard, The A.V. Club, Vulture, Alternative Press, Stereogum, The Village Voice, The Los Angeles Times, and Cleveland Plain Dealer. She is the author of a 33 1/3 book on Duran Duran’s Rio, Lady Gaga: Applause, and Pink: Raise Your Glass, and contributed an essay to Go All The Way: A Literary Appreciation of Power Pop, among others. She lives in Cleveland, Ohio.

Darling Clementine is a duo of designers and illustrators, Ingrid Reithaug & Tonje Holand. Ingrid and Tonje both did their university degrees in the UK, but are now working and living in Oslo. Since launching their independent stationery line in 2006, they have developed a worldwide brand with an extensive assortment, selling everywhere from Tokyo to Helsinki. Their style was the platform when establishing a design studio with the same name, undertaking a wide range of various commissions. These days, the business is divided in two sections, DC Creative & DC Decorative. DC Creative takes on all sorts of design and illustration commissions, alongside DC Decorative, who aims to develop and take care of the brand, constantly launching new products.

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