Throughout his career, Sinatra recorded several Christmas albums including 1948’s Christmas Songs by Sinatra, 1957’s A Jolly Christmas from Frank Sinatra, and 1968’s The Sinatra Family Wish You a Merry Christmas. Like many of Sinatra’s most believed albums, his Christmas recordings have been reissued and recompiled numerous times throughout the past few decades. That these recordings continue to captivate listeners is just another testament to Sinatra’s timeless talent.
We compiled a Spotify playlist with these songs that you can listen to here.
Here are five of Frank Sinatra’s best Christmas songs to get you swinging into the holiday season:
“Have Yourself a Merry Little Christmas”
“Have Yourself a Merry Little Christmas” is a quintessential Christmas song – so much so that Sinatra recorded it twice. When he first recorded the track in 1948, he was faithful to Hugh Martin and Ralph Blane’s lyrics. However, by the time he recorded A Jolly Christmas from Frank Sinatra, he had some changes in mind.
As the story goes, Sinatra asked Martin to rewrite one of the song’s more melancholic lines, “Until then we’ll have to muddle through somehow.” In 2020, Martin told Entertainment Weekly that said, “The name of my album is A Jolly Christmas. Do you think you could jolly up that line for me?” Jolly it up he did. Martin re-wrote the line to be “Hang a shining star upon the highest bow.”
“I’ll Be Home for Christmas”
“I’ll Be Home for Christmas” was written in 1943 by Kim Gannon and composed by Walter Kent. Bing Crosby – one of Sinatra’s great influences, first recorded the song in honor of soldiers who were overseas and lonesome for home. The song has been recorded by countless artists since its release. Of them all, Sinatra’s recording remains the only version that is equal to Bing’s.
“Let It Snow! Let it Snow! Let it Snow!” with the B. Swanson Quartet
With over 416 million streams on Spotify, “Let It Snow!” is one of Sinatra’s most famous – and highly played – recordings. (For context, “Fly Me to the Moon” has nearly 500M.) Sinatra recorded the track with the B. Swanson Quartet for his very first Christmas album, Christmas Songs by Sinatra. While the album is a Christmas classic, “Let It Snow!” stands out as the record’s highlight. It superbly encapsulates all that there is to love about Sinatra’s swing music.
Perhaps one of the most beloved Christmas songs of all time, Irving Berlin’s “White Christmas” won an academy award when it was first released in 1942. It’s been a mainstay of Christmas listening ever since.
The nostalgic, dreamy track recalls old-fashioned Christmases and simple moments of holiday bliss and tranquility. Meanwhile, Sinatra’s comforting baritone feels like a soft hand guiding us through a glistening Christmas village.
“Mistletoe and Holly”
When it comes to Christmas music, artists often stick to the age-old classics. Sinatra, however, co-wrote an original Christmas song in 1957. The track was “Mistletoe and Holly,” a number that taps into the anticipation we feel around the holiday season. He sings, “Then comes that big night / Giving the tree the trim / You'll hear voices by starlight / Singing a yuletide hymn.”
Queue “Mistletoe and Holly” while you’re trimming your tree this season!
Listen to this collection of songs with our Spotify playlist!
Natalli Marie Amato
Natalli Amato is a music and lifestyle journalist from Sackets Harbor, New York. Her bylines include Rolling Stone, Vice, and The Boot. She is also the author of several collections of poetry.