Feature Story

Favorite Holiday Songs

By Cyote Williams

12/4/2024

Christmas music floods the airwaves through our radios, Spotify and Apple Music playlists, or however you choose to listen to the holiday tunes year after year. While some think it criminal to start jingling bells before Thanksgiving, others begin rocking around the Christmas tree in their Halloween costumes. And all some want for Christmas is a silent night with holiday tunes regulated to the shadows for another year. We respect each of these opinions, but one way or another, Santa Claus is coming to town — and so is his music.

We, at CITYVIEW, sat down and discussed our favorite Christmas classics. From old to new, from good to bad. We noticed the classics rose to the top with not many newer songs making the list of favorites. Sure, a few crept in, like Mariah Carey’s, “All I Want for Christmas Is You,” Michael Bublé’s cover of “It’s Beginning to Look a Lot Like Christmas,” and Kelly Clarkson’s “Underneath the Tree,” which, having been released in 1994, 2011 and 2013, will soon be classics, too. Meanwhile, nearly every pop star, rapper, rock band and everything in between has released Christmas albums over the years.

The classics endure as part of the cherished holiday music many listened to growing up. They bring a sense of familiarity and nostalgia — the same feeling we get when friends and families put the same star on top of the tree, hang the same stockings and bake the same treats. It’s tradition. Kudos to the artists who have been able to make their way into the holiday music lexicon, and kudos to the artists whose songs have stood the test of time.

One issue we ran into while putting this list together was how to attribute the songs properly. Some of the original versions date back to the 1800s, while others have been covered more than 200 times. It seemed appropriate to attribute the songs to their originals and note some of the most famous renditions, too. All that leads us to our top 25 Christmas songs, in no particular order. To boot, we chose a few songs for our naughty list, too.

“White Christmas” — Irving Berlin, 1942

Famous renditions: Bing Crosby, Michael Bublé. Originally written by Irving Berlin in 1942 for the musical, “Holiday Inn,” Bing Crosby’s rendition is one of the most famous. Crosby’s version of the recording spent 11 weeks atop the Billboard Charts.

“The Little Drummer Boy (Carol of the Drum)” — Katherine Kennicott Davis, 1941

Famous renditions: Bing Crosby and David Bowie, Harry Simeone Chorale, Frank Sinatra. This song was first recorded in 1951 but gained popularity in 1958 thanks to Harry Simeone Chorale. It’s been said the inspiration came to Davis from the French song “Patapan’” which then translated in her mind to “pa-rum-pum-pum.”

“Feliz Navidad” — José Feliciano, 1970

Famous renditions: Celine Dion, Cast of Glee. Spanish for “Merry Christmas,” the song “Feliz Navidad” was inducted into the Grammy Hall of Fame in 2010. The iconic track was recorded in 10 minutes, and its lyrics include only 19 words. Keep it simple.

“Santa Claus Is Coming to Town” — Harry Reser, 1934

Famous renditions: Bruce Springsteen, The Jackson 5. Written by J. Fred Coots and Haven Gillespie, the song became a hit after it was covered by Eddie Cantor and sold 500,000 copies of sheet music and 30,000 records within the next 24 hours. The popular holiday track has been covered by more than 200 artists.

“Rockin’ Around the Christmas Tree” — Brenda Lee, 1958

Famous renditions: Cyndi Lauper, Ronnie Spector and Darlene Love. Brenda Lee’s track has sold more than 36 million copies, the fifth-most digital downloads sold of any Christmas single. In November of 2023, Lee released a music video for the song, and, by December, it topped the U.S. Billboard Hot 100 chart, making her the oldest artist to do so at age 78. A week later, she broke her own record by turning 79.

“Rudolph the Red-Nosed Reindeer” — Gene Autry, 1949

Famous renditions: The Temptations, Paul McCartney. This one is a childhood favorite movie turned famous Christmas song. Johnny Marks’ brother-in-law, Robert L. Mays, created the character, Rudolph. Ten years later, Marks wrote the lyrics and Gene Autry recorded the song, which went on to hit No. 1 in the U.S. during that year’s Christmas season.

“The Christmas Song” (“Chestnuts Roasting on an Open Fire”) — Nat King Cole, 1946

Famous renditions: Danny Boy, Aretha Franklin. This is another song that has been covered time and time again. The original 1946 recording was inducted in the Grammy Hall of Fame in 1974, and, in 2022, the 1961 recording was selected by the Library of Congress for preservation in the National Recording Registry.

“All I Want for Christmas Is You” — Mariah Carey, 1994

Famous renditions: Justin Bieber, Fifth Harmony. Mariah Carey’s song shoots up the streaming charts in the weeks leading up to Christmas. It has reached No. 1 status in more than 30 countries, and, since 2019, the song has hit No. 1 on The Hot 100 chart every year. The song is one of the few to break through the hold the classics have on the genre. The Associated Press estimated the song has earned more than $100 million in royalties.

“Silent Night” — Franz Xaver Gruber, 1818

Famous renditions: Bing Crosby, Mariah Carey, Boyz II Men. A popular choice for Christmas carolers, in a list full of songs with hundreds of covers, “Silent Night” tops them all. According to Billboard, there are more than 137,000 known recordings of the English version of the German song, “Stille Nacht.”

“Have Yourself a Merry Little Christmas” — Judy Garland, 1944

Famous renditions: Frank Sinatra, Lito Magnaye, Sam Smith. Brought to the mainstream by Judy Garland in the musical “Meet Me in St. Louis,” the American Society of Composers, Authors and Publishers (ASCAP) ranked the tune as the third-most performed Christmas song.

“You’re a Mean One, Mr. Grinch” — Thurl Ravenscroft, 1966

Famous renditions: Jim Carrey, Tyler, The Creator.Written by Theodor “Dr. Suess” Geisel, the song, story and movie has been adapted several times since the original in 1966. Jim Carrey starred in and performed the 2000 live-action version. In 2018, Tyler, The Creator, performed the song in the 2018 CGI adaptation.

“It’s Beginning to Look a Lot Like Christmas” — Perry Como, 1951

Famous renditions: Michael Bublé, Bing Crosby. There is a dispute about the lyrics of this song that could tie it to Iowa. Originally written by Meredith Wilson, a Mason City native, it’s possible he mentions the Historic Park Inn Hotel, designed by Frank Lloyd Wright, which sits in his hometown, referring to a “tree in the Grand Hotel, one in the park as well.” The other thought is he’s referencing Yarmouth’s Grand Hotel in Yarmouth, Nova Scotia.

“Underneath the Tree” — Kelly Clarkson, 2013

Modern Christmas classics are hard to come by, but the first winner of American Idol, Kelly Clarkson, managed to give us one. In 2021, the ASCAP named it the most-popular Christmas song released in the 21st century.

“Winter Wonderland” — Richard Himber, 1934

Famous renditions: Frank Sinatra, Elvis Presley. Written by Felix Bernard and Richard Bernard Smith, Smith says he was inspired to write the lyrics after seeing Honesdale, Pennsylvania’s, central park covered in snow. Most recently, a recording by Chlöe became the first version to enter the Hot 100.

“A Holly Jolly Christmas” — Burl Ives, 1962

Famous renditions: Lady Antebellum, Michael Bublé. This is another song penned by Johnny Marks. This one is sung by Burl Ives, who also voiced the narrator, Sam the Snowman, in the popular children’s movie “Rudolph the Red-Nosed Reindeer.”

“Blue Christmas” — Doye O’Dell, 1948

Famous renditions: Elvis Presley, Train. While Doye O’Dell was the first to record the song written by Billy Hayes, Ernest Tubb, conductor Hugo Winterhalter and Russ Morgan’s versions led to its popularity. Eventually covered most famously by Elvis Presley in 1964, the King’s version peaked at No. 1 on Billboard’s U.S. Christmas Singles chart and 18th on its Hot 100 chart.

“Frosty the Snowman” — Gene Autry and the Cass County Boys, 1950

Famous renditions: The Jackson 5, Billy Idol. This classic was written by Walter “Jack” Rollins and Steve Nelson after the success of Autry’s “Rudolph the Red-Nosed Reindeer” song. Autry was looking for another holiday hit and agreed to record the song, leading to another popular Christmas character in “Frosty.”

“It’s the Most Wonderful Time of the Year” — Andy Williams, 1963

Famous renditions: Harry Connick Jr., Amy Grant. Andy Williams’ song, written by Edward Pola and George Wyle, still cracks the charts in modern times — partially because it’s a favorite for radio stations. In 2024, a sample of 20 stations that switched to Christmas music before Veterans Day, five of the stations chose Williams’ song, tied with Mariah Carey’s “All I Want for Christmas Is You,” for first.

“Deck the Halls” — Nos Galan, 1862

Famous renditions: Pentatonix, The Red Hot Chili Peppers. Fa, la, la, la, la, la, la, la, la.

“Jingle Bell Rock” — Bobby Helms, 1957

Famous renditions: Billy Idol, Hillary Duff, George Strait, Hall & Oates. Bobby Helms’ version of this song went platinum in seven countries: Australia, Denmark, Italy, New Zealand, Portugal, U.K. and Greece. There is some controversy surrounding the song. Helms and guitarist Hank Garland both claim they wrote the song, not Joe Beal and Jim Boothe, saying they changed the original, “Jingle Bell Hop,” to what so many listen to today.

“Let It Snow! Let It Snow! Let It Snow!” — Vaughn Monroe, 1945

Famous renditions: Dean Martin, Frank Sinatra. Sammy Cahn and composer Jule Styne wrote the track with the easy-to-remember title. Released in 1945 right after Thanksgiving, the song was a hit by Christmas. However, a quick look at the lyrics shows it makes no mention of the holidays. Still, it is still synonymous with the season.

“Hark! The Herald Angels Sing” — Charles Wesley and George Whitefield, 1739

Famous renditions: Nat King Cole, Bob Dylan. This is by far the oldest song on this list. The tune first appeared in the collection of Hymns and Sacred Poems in 1739 and is based on Luke 2:14, which tells of an angelic chorus singing the praises to God.

“I’ll Be Home for Christmas” — Bing Crosby, 1943

Famous renditions: Whitney Houston. This Christmas song, written by Walter Kent and James “Kim” Gannon, honors soldiers during World War II. While this song is somewhat somber, GI magazine “Yank” said Crosby “accomplished more for military morale than anyone else of that era.”

“The Twelve Days of Christmas” — Frederic Austin, 1909

Famous renditions: John Denver and The Muppets, Fay McKay. English composer Frederic Austin must have had plenty of room under his tree for a partridge in a pear tree, two turtle doves, three French hens, four colly birds, five golden rings, six geese a-laying, eight maids a-milking, nine ladies dancing, 10 lords a-leaping, 11 pipers piping and 12 drummers drumming.

“Step Into Christmas” — Elton John, 1974

Elton John’s Christmas song has gained more popularity in recent years than it did upon release. In 1974, it peaked at No. 24 on the U.K. Singles Chart but reached No. 8 in 2019 and has cracked the top 20 every year since 2017. ♦