Best Christmas Singers of All Time

To countdown the Best 30 Christmas Singers of All Time we put together a panel of Christmas music lovers to choose the top artists.

Christmas music is unique in that for many fans it takes over their music listening time – in the car, home or office – for a few weeks. No other holiday music or occasion is quite like that.

With hot cocoa and a smorgasbord of Christmas cookies, we set about trying to identify the individuals who sang the best when it came to Christmas songs. The rankings are based on the body of work and not one individual song (which ruled out many one-hit Christmas song wonders).

There were lively arguments, cases pled with vigor, and at times some sharp disagreements, but ultimately the following list was agreed on.

See if you agree or disagree as we countdown the list from #30 to #1.

Christmas Singers and Songs — #30 – #21

Believe me, it was difficult for our panel to stop at just the top 30 Christmas singers. But, we did and here they are.

#30 – Michael Bublé

The Canadian has a knack for song selection especially when he zeroes in on Sinatra’s arrangements. A few on the panel pushed for a higher position for this crooner, but he lands at our #30 slot.

“It’s Beginning to Look a Lot Like Christmas” by Michael Bublé

#29 – The Temptations

One of the biggest hit-makers on Motown’s deep roster, The Temptations might be everyone’s pick to see in a Christmas concert. With their stylish moves and beautiful harmonies, The Temptations’ success also transferred easily to Christmas songs. Here’s one of our favorites.

“Rudolph the Red-Nosed Reindeer” by The Temptations

#28 – Peggy Lee

With a career spanning six decades, Peggy Lee was a jazz and pop singer who was nominated for 12 Grammy awards. Hailing from Jamestown, North Dakota, she sang with the Goodman’s Orchestra.

“Santa Claus is Coming to Town” by Peggy Lee

#27 – Rosemary Clooney

One of the star’s of the movie “White Christmas,” Clooney is known for many of the songs associated with that classic. She’s also known for being the aunt of actor George Clooney.

“Count Your Blessings” by Rosemary Clooney

#26 – Taylor Swift

The singer-songwriter noted for her breakup songs with exes is no stranger to Christmas music. Swift has record sales of over 200 million records making her one of the biggest musical stars of all time. She counts Shania Twain and Stevie Nicks as a couple of her influencers in the music field.

“Last Christmas” by Taylor Swift

#25 – Harry Connick, Jr.

The jazzy pianist and singer from New Orleans has ten number-one jazz albums to his credit. Connick provided the soundtrack to the famous movie, “When Harry Met Sally.” His approach to Christmas music reflects his jazz and New Orleans roots.

“(It Must’ve Been Ol’) Santa Claus” by Harry Connick, Jr.

#24 – The Supremes

The most successful band to come out of Motown, the all-female singing group had 12 number-one songs. Most of their hits were written by the famed Motown writing team of Holland-Dozier-Holland. The Supremes’ “Merry Christmas” album featured many classic favorites like “White Christmas” and “Joy to the World.”

Their version of “My Favorite Things” was featured in the 2018 version of the film “The Grinch.”

“My Favorite Things” by The Supremes

#23 – Tony Bennet

From his signature song, “I Left my Heart in San Francisco,” to his longevity in performing music (sometimes with the hippest of stars), Tony Bennett is all about the music. He takes on Christmas favorites with the same relish: Classy and Stylish.

“Winter Wonderland” by Tony Bennett

#22 – Doris Day

Doris Day recorded more than 650 songs in a 20-year time frame from 1947 to 1967 and some of those were Christmas songs. You might also know her from movies she acted in like “Pillow Talk” with Rock Hudson or Alfred Hitchcock’s “The Man Who Knew Too Much.”

Early in her life, Doris studied to be a dancer but a car accident injured her leg. Given her music, acting, and activist success, I guess we can say that it turned out alright for her.

“Silver Bells” by Doris Day

#21 – Mel Torme

Did we give Mel Torme a few bonus points for not only singing “The Christmas Song,” but also writing and composing it? Yes! But, who wouldn’t for such a classic?

“The Christmas Song” by Mel Torme

Christmas Classic Favorites — #20 – #11

#20 – The Beach Boys

Ok, so most people don’t associate California with Christmas songs, but remember Irving Berlin’s “White Christmas” was written in Los Angeles, California. The Beach Boys’ harmonies shine in this classic, “Little Saint Nick.”

Heavily influenced by Phil Spector over the course of his career, Brian Wilson wrote “Little Saint Nick.”

“Little Saint Nick” by The Beach Boys

#19 – Andy Williams

Born in Wall Lake, Iowa, Andy Williams was a singer, record producer, and TV star. Williams recorded 43 albums in his career and 15 were gold-certified and 3 were platinum-certified.

Of the 43 albums he recorded, eight of them were Christmas albums earning the nickname, “Mr. Christmas.”

His TV show was a showcase for his songs and the Christmas shows frequently featured this hit that is now associated with Andy Williams.

“It’s the Most Wonderful Time of the Year” by Andy Williams

#18 – Elvis Presley

Elvis’s favorite Christmas song: “Blue Christmas.” Need we say more?

“Blue Christmas” by Elvis Presley with Martina McBride

#17 – Perry Como

The Italian-American star, born in Canonsburg, Pennsylvania, was nicknamed, “Mr. C.” BillBoard Magazine summarized his life in 13 words: “50 years of music and a life well lived. An example to all.”

Perry was the 7th of 10 children who didn’t speak English until he entered school as the family spoke Italian at home. Como was influenced by Bing Crosby and often compared to him.

“It’s Beginning To Look A Lot Like Christmas” by Perry Como

#16 – John Legend

John Legend, aka John Roger Stephens, does it all. He’s a singer, songwriter, actor, film producer, record producer and theatre director. Born in Springfield Ohio, he is married to Instagram sensation and model Chrissy Teigen.

This song is off of his 2018 album A Legendary Christmas.

“Have Yourself a Merry Little Christmas” by John Legend with Esperanza Spalding

#15 – The Blind Boys of Alabama

This group started in 1939 and has featured a changing roster of performers. Many of the band members are visually impaired. Their cover of Tom Waits song “Way Down in the Hole” was one of the versions of theme songs used for the legendary HBO series, “The Wire.”

Clarence Fountain provides lead vocals with country singer Shelby Lynn on this song. Fountain was a founding member of the group and passed away in 2018.

The group has won five Grammy awards.

“The Christmas Song” by The Blind Boys of Alabama featuring Shelby Lynne

#14 – Burl Ives

Burl Ives holds a special place in the hearts of Christmas enthusiasts. Not only does he narrate the 1964 version of Rudolph the Red-Nosed Reindeer TV Special as Sam the Snowman, but also through his many Christmas songs. And, here is perhaps his most noteworthy.

“A Holly Jolly Christmas” by Burl Ives

#13 – Johnny Mathis

73 of Johnny Mathis’s albums made the Billboard Charts – six of them were Christmas albums. Influenced by Nat King Cole, Bing Crosby and others, Mathis had a smooth and easy singing style. He is of African-American and Native-American heritage, and the fourth of seven children.

Fun fact about Johnny Mathis: He was second in the high jump in the city of San Francisco only to future NBA star Bill Russell while in college. He was a great all-around athlete excelling at high jumping, hurdling, and basketball.

“Sleigh Ride” by Johnny Mathis

#12 – Gene Autry

Nicknamed “The Singing Cowboy,” Autry appeared in 93 films and was a pioneer in the country music genre of music. Autry is the only person on the Hollywood Walk of Fame to be awarded stars in five categories: film, TV, music, radio and live performance.

His Christmas songs are traditional favorites and include the likes of “Rudolph, the Red-Nosed Reindeer,” “Frosty the Snowman,” and “Up on the Housetop.” But, we’re going with “Here Comes Santa Claus” for our showcase.

“Here Comes Santa Claus” by Gene Autry

#11 – The Jackson Five

The Jackson Five Christmas Album released in 1970, like their other albums, was a huge hit. It was one of 10 albums released by Motown. When the group moved to CBS/Epic, they became known as The Jacksons.

Michael Jackson’s solos, as usual, set the tone. The group’s versions of “Santa Claus is Coming to Town,” and “I Saw Mommy Kissing Santa Claus” were the two biggest hits off the album. But, one of our favorites is featured below.

“Give Love on Christmas Day” by The Jackson Five

The Top Christmas Singers – #10 – #1

Top Ten Christmas Singers Meme

#10 – Whitney Houston

The most awarded female artist of all time (per Guinness World Records) can absolutely belt out a song. Having begun singing as a child at her church, she always seemed very comfortable with Christmas songs. “One Wish” is no exception.

Tony Bennett once said, “When I first heard her, I called Clive Davis (Houston’s producer) and said, ‘You finally found the greatest singer I’ve ever heard in my life.'”

“One Wish (For Christmas)” by Whitney Houston

#9 – Bobby Darin

Darin could play the piano, drums and guitar as a teenager. “The Latin Lover” was as smooth as silk in nightclub concerts and defined “cool” for many fans. He was married to actress Sandra Dee for seven years.

Darin had a keen interest in chess. His TV show had a segment where he would explain chess moves. Perhaps his most famous song is “Mac the Knife,” but as you’ll hear in “Christmas Auld Lang Syne,” his talents were many.

“Christmas Auld Lang Syne” by Bobby Darin

#8 – Stevie Wonder

This was a tough pick. Should we go with “Someday at Christmas” or “That’s What Christmas Means To Me”? We went with the latter for our featured song – really couldn’t go wrong.

#7 – The Ronettes (Ronnie Spector)

“A Christmas Gift for You from Phil Spector” showcased three songs from the Ronettes including “Frosty the Snowman,” “I Saw Mommy Kissing Santa Claus,” and “Sleigh Ride.” Other performers on the album include Darlene Love and The Crystals.

In 2019, this album was selected as the greatest Christmas album of all time by Rolling Stone. The Beach Boys’ Brian Wilson has also given it high honors by calling it his favorite album of all time.

“Frosty the Snowman” by The Ronettes

#6 – Dean Martin

Like Bobby Darin, Dean Martin was known for being suave. In fact, his nickname was “The King of Cool.”

His career breakthrough came as a result of partnering with Jerry Lewis for numerous Martin and Lewis movies. A member of the “Rat Pack,” he was tight with Frank Sinatra and Sammy Davis Jr.

In addition to his Christmas songs, he’s associated with “That’s Amore,” “Everybody Love Somebody,” and “Ain’t That A Kick in the Head.”

“Let it Snow! Let it Snow!” by Dean Martin

#5 – Frank Sinatra

Ol’ Blue Eyes could sing just about any song he set his mind to. The Sultan of Swoon from Hoboken, New Jersey, worked hard at his craft. His blessing to others: “May you live to be 100 and may the last voice you hear be mine.”

Unlike many syrupy Christmas songs, “Have Yourself a Merry Little Christmas” is more subdued reflecting its WW II time period. Judy Garland introduced the song in the movie “Meet Me in St. Louis.”

“Have Yourself a Merry Little Christmas” by Frank Sinatra

#4 – Bing Crosby

“White Christmas” was written by Irving Berlin and released in 1942. Bing Crosby’s version is the best selling song of all time having sold over 50 million copies.

Berlin said of the song to his secretary, “I want you to take down a song I wrote over the weekend. Not only is it the best song I ever wrote, it’s the best song anybody ever wrote.”

The opening verse is frequently left out, but important to set the mood. Here it is:

“The sun is shining, the grass is green,
The orange and palm trees sway.
There’s never been such a day
in Beverly Hills, L.A.
But it’s December the twenty-fourth,—
And I am longing to be up North —”

“White Christmas” by Bing Crosby

#3 – Nat King Cole

Nat King Cole, born Nathaniel Adams Cole in Montgomery, Alabama, was the first African-American to host an American TV show. He had 100 songs that made it to the pop charts.

Daniel Mark Epstein wrote of the singer, “Nat King Cole’s voice is really one of the great gifts of nature… Remember, he was never trained as a singer. And so, his voice is absolutely pure. He’s a baritone with absolutely perfect pitch. He sings the notes true and he hits them right in the center.”

Natalie Cole, a musical star in her own right, was his daughter.

“Hark the Herald Angels Sing” by Nat King Cole

#2 – Ella Fitzgerald

The First Lady of Song, Lady Ella, and the Queen of Jazz were just some of Ella Fitzgerald’s monikers. She is known for her beautiful tone, scat singing, timing, and phrasing.

She won 14 Grammy awards and the Presidential Medal of Freedom.

As the singer Hozier said, “There is no singer I can think of who can touch Ella Fitzgerald.”

“Baby, It’s Cold Outside” by Ella Fitzgerald with Louis Jordan

#1 – Karen Carpenter (The Carpenters)

If you’ve ever listened to a Carpenters’ song without the musical accompaniment you get an idea of just how pure Karen Carpenter’s voice was. The Carpenters made two Christmas albums.

Producer Paul Williams said, “Somebody was talking about their sound being ‘vanilla’ at one point and I went but what an exquisite flavor vanilla is. They made great records. They took our songs and gave them a life.”

And, that’s why they’re the best Christmas singers of all time.

“Merry Christmas, Darling” by The Carpenters

“The Christmas Waltz” by The Carpenters

There you have it, the Best Christmas Singers of All Time. When you put together your Spotify list, consider some of the songs featured above as inclusions.

— Emily Ryan, Greg Johnson, & Mike O’Halloran

Emily, Greg, and Mike are music enthusiasts.

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