16 Saddest Christmas Songs: Crushing Winter Blues

Saddest Christmas Songs

It’s that time of year again. The days are shorter, the air is colder, and there’s supposed to be a twinkle in your eye when you think about Christmas. But now and then, it can be hard to get into the holiday spirit. This season, many of us experience sadness or loneliness for various reasons. And sometimes it feels like Christmas music doesn’t provide any comfort. Around this time, you’ll be more likely to be looking for the saddest Christmas songs, rather than chipper ones. So if you’re feeling blue this holiday season and have resisted putting up your Christmas Tree, this list of The Saddest Christmas Songs may help you feel understood.

Remember, you’re not alone.

Saddest Christmas Songs

Judy Garland/Frank Sinatra – Have Yourself A Merry Little Christmas

Hugh Martin initially wrote this song for the movie “Meet Me In St. Louis” and was sung by Judy Garland. It’s a classic Christmas song, but it can be pretty sad if you listen to the lyrics. “Have Yourself A Merry Little Christmas” is one of those songs that makes you feel nostalgic and sad all at the same time. It’s a reminder that sometimes things don’t go as planned during the holidays, which can be difficult for some people. With lyrics like “through the years, we all will be together, if the fates allow,” it is a bittersweet reminder that sometimes the ones you love are no longer here. For me, it is the saddest Christmas song.

While Judy Garland would be the original performer, Frank Sinatra would perform a classic version of the Christmas classic, with slightly modified lyrics. However, both are brilliant in their own right and deserve a listen.

Frank Sinatra – Whatever Happened To Christmas / Saddest Christmas Songs

Frank Sinatra’s “Whatever Happened To Christmas” was recorded in 1968 and released on his album “The Sinatra Family Wish You a Merry Christmas.” The song is a nostalgic look back at Christmases’ past and how they don’t seem to be the same anymore. While not as popular as other songs on this list, it’s a sentiment that many people can relate to, as the past few years have been difficult for many. Whether it’s the isolation that Covid brought families in 2020, the stress of the world, or the losses of loved ones, many may feel the Holidays aren’t as magical as they once were.

If you’re missing Christmases gone by, or feeling sad about what Christmas has become, give this song a listen.

Vera Lynn / Nat King Cole – The Little Boy That Santa Claus Forgot/ Saddest Christmas Songs

The Little Boy That Santa Claus Forgot is a dark tale written in 1937 and performed by Vera Lynn. This depressing Christmas song tells the story of a young boy left out by Santa Claus. He sees other youngsters playing with their toys and feels lonely and disappointed. His Christmas Day is just another dreary day since he has no one to give him gifts or join in the celebration. It turns out that he doesn’t have a father, explaining the real reason why he isn’t receiving gifts this year.

The song is a poignant reminder that not everyone has a Merry Christmas. However, it’s also a reminder to be grateful for what we do have, even if our holiday season isn’t as merry as we’d like it to be. Nat King Cole also recorded a rather lovely version of this song.

Bing Crosby – I’ll Be Home For Christmas

I’ll Be Home For Christmas is a sad holiday song about longing to be with loved ones. The lyrics describe the feelings of a soldier who is away from his family during the holidays and wishes he could come home for Christmas. However, a close inspection of the lyrics suggests that the soldier may not be making it home, as the song closes with “I’ll be home for Christmas, if only in my dreams.” In addition to being a sad song, I’ll Be Home For Christmas was written during World War II. This adds an extra element of sadness as the lyrics describe what it’s like for those stationed overseas in one of the world’s deadliest wars.

Elvis Presley – Blue Christmas / Saddest Christmas Songs

The song Blue Christmas is a gloomy ballad about unrequited love. The lines illustrate a person’s anguish over not having their crush’s love during the holidays and being lonely without them. Doye O’Dell sang it for the first time in 1948, although the most popular version was by Elvis, who made Blue Christmas a holiday standard.

The Carpenters – Merry Christmas Darling / Saddest Christmas Songs

The song “Merry Christmas, Darling” was initially penned by Frank Pooler in 1944. Still, it wouldn’t be recorded until years later when he gave Karen and Richard Carpenter the words. While the meaning of the lyrics may be interpreted in various ways, Karen’s version conveys the sentiment that she is grieving for a departed loved one who is no longer able to share Christmastime with her.

The Carpenters recorded the song in 1970, and it has since become a Christmas classic. It’s a slower-paced song, but the lyrics are so beautiful that they will touch your heart. Karen Carpenter’s voice is absolutely angelic in this recording, and it’s no wonder why the song has been covered by so many artists over the years.

If you’re feeling lonely this Christmas, or miss someone special, give “Merry Christmas Darling” a listen.

The Everly Brothers – Christmas Eve Can Kill You/ Saddest Christmas Songs

The Everly Brothers released “Christmas Eve Can Kill You” in 1972 as part of their Stories We Could Tell album. The song is another sad one that talks about the isolation of Christmastime. Beginning with recollections of years past, the music switches to the viewpoint of a man stranded on a cold winter night, trying to find a ride anywhere. The character watches as cars pass him by, not giving him a second thought as he makes his way through the dangerous cold. With lyrics like “Christmas Eve can kill you when you’re trying to hitch a ride to anywhere,” it’s undoubtedly one of the darkest songs on this list.

Eagles – Please Come Home For Christmas/ Saddest Christmas Songs

Covered many times since its inception, Please Come Home For Christmas was first performed by Charles Brown. The lyrics are a plea from someone who misses his loved one and wants her to come home for Christmas because he knows that the holidays would not be so cheerful without her. Covered by The Eagles in 1978, the lyrics were changed from “glad, glad, news” of the original Charles Brown version to “sad, sad, news.” The Eagles’ interpretation of the song went to #18 on the Billboard Hot 100 and was a smash hit for the band. Nowadays, the Eagles’ cover is the most recognized version.

Band-Aid – Do They Know It’s Christmas?/ Saddest Christmas Songs

Do They Know It’s Christmas? Is a song that was written in 1984 by Bob Geldof and Midge Ure. The lyrics were inspired by the devastating famine in Ethiopia. The original version of the song featured many pop stars, including Bono, George Michael, and Phil Collins.

Many articles have subsequently mocked the irony of extremely wealthy musicians attempting to compel listeners with lyrics like “well, tonight thank God it’s them, rather than you.” The lyric, as mentioned earlier, has already drawn criticism to the song, as contemporary opinions consider it to have a very Western-colonialist viewpoint. Other complaints have been leveled towards the song for having stereotypical views of Africa. A product of its time, there’s no denying it has its flaws. However, the song’s sad message about poverty and hunger makes it worthy of inclusion in our minds.

Wham! – Last Christmas / Saddest Christmas Songs

Have you ever been dumped around the holidays? Wham!’s Last Christmas is ideal for you if that’s the case. In this song, a broken-hearted George Michael sings about an ex-girlfriend who let him down Last Christmas, vowing to give his heart to “someone special” this year. He sees the woman who hurt him the following year, and he endeavors to avoid her. However, he cannot shake the influence she still has on him.

As he grapples with his feelings, George promises never to trust her again, with a sassy “So Long!” tacked on at the end for good measure. While a bit happier sounding than some of these tracks, the lyrics of Last Christmas still hold true for anyone nursing wounds from a holiday breakup.

Newsong – Christmas Shoes / Saddest Christmas Songs

A melancholy Christmas song from NewSong, titled “Christmas Shoes,” tells the story of a youngster who wishes to get his dying mother shoes for Christmas. If she sees Jesus tonight, the kid hopes desperately that her mother will look her ‘best,’ to make her feel ‘special.’ However, depending on your feelings on the song, you may be more depressed being compelled to sit through it. After all, it was voted one of the Worst Christmas Songs Ever.

Linkin Park – My December/ Saddest Christmas Songs

“My December” by Linkin Park is a song about the difficulties of being alone during the holidays and dealing with regret, isolation, and memories of mistakes made. This song, released as part of Almost Acoustic Christmas 2000 on KROQ, is one of Linkin Park’s gentlest and quietest tracks. In this song, Chester Bennington sings about snow-covered trees, houses and pretends that the holiday’s beauty is enough to make him happy. However, as he reviews the circumstances and mistakes he’s made, he wishes he could give it all away just to feel complete again.

Old Sea Brigade – If We Make It Through December/ Saddest Christmas Songs

Old Sea Brigade’s cover of Merle Haggards “If We Make It Through December” is a profoundly sorrowful song. The lyrics are delivered from the perspective of a father trying to survive the winter financially after being laid off from his factory job. He’s concerned about telling his daughter he won’t be able to afford Christmas this year. While some people may believe that the purpose of Christmas is not the presents, this song leaves an impression. All parents who have struggled to make it through a holiday will understand.

Coldplay – Christmas Lights/ Saddest Christmas Songs

Christmas Lights is a sad ballad about an awful fight on Christmas Eve. It’s the narrative of a guy walking down a well-decorated street, racked with anguish over a breakup. In this song, the protagonist attempts to find joy in holiday decorations and symbolism as he thinks back on everything he did wrong. But, try as he might, he can’t shake the feeling of missing his significant other, as without her, it “doesn’t really feel like Christmas at all.”

Auld Lang Syne / Saddest Christmas Songs

While not a Christmas song per se, Auld Lang Syne is played throughout the holidays and seems to fit this list. Auld Lang Syne is a Scottish poem written by Robert Burns in 1788. The song is about reminiscing on old friendships and times gone by. It asks the listener, should old times be forgotten? It’s often sung at the end of New Year’s celebrations as people make resolutions for the coming year. However, given its lyrics, it is also played at funerals or other events where a farewell may be necessary.

The lyrics are beautiful, and they offer a sad reminder that time waits for no one. We lose loved ones and friends as the years go by, and looking back can be bittersweet. There are many versions of the song, but Susan Boyle’s performance is somber.

Ed Sheeran & Elton John – Merry Christmas / Saddest Christmas Songs

Ed Sheeran and Elton John’s Merry Christmas is a brand-new song that was just released this year. It’s an exquisitely beautiful piece, and it will undoubtedly end up on Christmas Classic playlists in the years to come. The song is a duet, with Sheeran and John singing the verses. The song is a heartbreaking warning to enjoy the holidays with the ones you love because “next year you never know.”

Both artists have had successful careers, but it’s lovely to hear them sing together as their vocals compliment each other perfectly. So if you’re feeling nostalgic for Christmases gone by, or simply want a feel-good Christmas song, give this one a listen.


The most popular Christmas songs are often the Saddest Christmas Songs. If you’re experiencing another lonely Christmas and lacking that Christmas feeling, we hope our list of sad Christmas songs can help you feel less alone. What is your favorite sad Christmas song for these cold December nights? Let us know in the comments! And don’t forget to share this post with your friends and family. Happy Holidays!

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