25 of the most heartbreaking Christmas songs

Christmas is often called “the most wonderful time of the year.” However, for many people, it can also be the most isolating and melancholy season. In fact, countless holiday hits are far more gut-wrenching than cheerful. Here are 25 of the most heartbreaking Christmas songs. 

“Last Christmas” is a classic holiday song, but it’s also one of the most gut-wrenching. The track is about experiencing heartbreak and grief during the Christmas season, recalling an old lover who broke the narrator’s heart. If you’re going through a breakup, perhaps avoid this triggering tune, as it might sabotage your holiday spirit. 

I will never forget when I first heard “The Christmas Shoes.” The song is from the perspective of a last-minute shopper rushing about, only to be held up in line by a little boy who’s attempting to purchase shoes for his mother. As the man overhears the little child's conversation with the cashier, he learns the boy’s mom is sick and doesn’t have much time left. The child is desperate to buy the gift, because “I know these shoes would make her smile, and I want her to look beautiful if mama meets Jesus tonight.” The song reminds us of the important things in life, like our loved ones and our health. 

“River" is another emotional yet deeply relatable Christmas song. Don’t we all wish we could skate away from our problems on a pristine frozen river? The track is about loss, regret, and guilt—three agonizing experiences only worsened by the holiday season.

Given its name, you can likely assume “Blue Christmas” is about experiencing a rather melancholy holiday. While the song might be catchy, it’s one of the saddest Christmas songs out there, detailing the pain of spending the holiday without your (past) lover. This season often triggers grief and loneliness, but missing someone can make it even more agonizing. 

Another heartbreaking holiday song, “Christmases When You Were Mine” by Taylor Swift, recalls past holidays spent with a lover who is no longer in the person’s life. Leave it to Taylor to turn the most cheerful time of the year into a painfully reflective period of longing. Unfortunately, this is a feeling many of us know all too well.

“Merry Christmas, Darling” has always been a romantic yet heartbreaking Christmas song. This hit is about being apart from your lover during Christmas. Sung with pensive vocals, the lyrics are as emotional as the melody itself: “I've just one wish on this Christmas Eve: I wish I were with you.”

“Christmas Lights” by Coldplay is about searching for a lost love that’s no longer in your life. Not only is the melody gut-wrenching, but the lyrics are pretty much the opposite of merry: “Singing how I always loved you, darling, and I always will. When you're still waiting for the snow to fall, it doesn't really feel like Christmas at all.”

“So Much Wine” by emo, indie-folk singer/songwriter Phoebe Bridgers is about watching a loved one suffer from alcoholism, desperately trying to escape their woes on Christmas Day. Unfortunately, as Phoebe sings, “Listen to me, butterfly, there's only so much wine that you can drink in one life. And it will never be enough to save you from the bottom of your glass.” This song was originally released by the American folk duo The Handsome Family, but Phoebe’s version has become a popular, perhaps even more haunting, cover.

Christmas is often marketed as an abundant time of the year, with expensive gifts and flashy celebrations. However, some ignore the harsh reality that many families can’t afford such blessings. “Hard Candy Christmas” describes a holiday where everyone is simply trying to make ends meet—where the most luxurious gifts come in the form of hard candies, both literally and metaphorically.

Any time this song comes on, I immediately have chills down my arms. Known from the popular Christmas movie The Polar Express, “When Christmas Comes to Town” reminds us that much of the magic of Christmas is a privilege many children don’t get to experience. From the opposite perspectives to the gorgeous, childlike harmonies, this song will bring you to tears.

The Christmas season can make anyone feel lonely and nostalgic, but it’s especially harsh on the heartbroken. Relient K’s “I Hate Christmas Parties” describes the experience of slowly losing your lover, feeling them pull away during the holidays. Rather than gifts under the tree, the narrator is getting a broken heart from the person he loves the most. 

“Where Are You, Christmas?” describes the nostalgia and loss of magic many of us face during the holiday season. As we grow up and face adult realities/hardships, it can be difficult to connect with the lighthearted warmth of Christmas. This mournful song might be heartbreaking in many ways, but its ending lyrics also offer a sense of hope: “I feel you Christmas. I know I've found you. You never fade away. The joy of Christmas stays here inside us, fills each and every heart with love.”

“My Grown Up Christmas List” by Natalie Cole is a song most adults can relate to. While we once filled our letters to Santa with lists of the latest and greatest toys or electronics, as we’ve grown, we've begun to seek deeper, less attainable gifts. The narrator’s “grown-up Christmas list” consists of the following requests: “No more lives torn apart / That wars would never start / And time would heal all hearts / And everyone would have a friend / And right would always win / And love would never end.”

This bitter holiday song calls out a past partner/friend who has wronged the narrator. While the lyrics ultimately wish the individual well, they also make it clear that they won’t be around to talk to them anymore. “Merry Christmas, Please Don’t Call” is the exact words many of us would like to text a toxic ex-lover or two who won’t seem to leave us be. This atmospheric, synth-pop song is deeply relatable, yet heartbreaking nonetheless.

It’s clear by the title of this track that it’s more of an anti-war anthem than a cheerful Christmas song. Its hopeful, catchy tune disguises its plea for peace, while reminding listeners of the harshness of the world. However, the lyrics also highlight our influence and power: “And so this is Christmas (War is over) / For weak and for strong (If you want it).”

Band Aid’s “Do They Know It's Christmas?” gently calls out the privilege of relishing the holiday season. The lyrics remind listeners of the countless individuals across the world living in famine-stricken regions, unable to enjoy the blessings of the season or even have their basic needs met. It urges the fortunate individuals to express gratitude and give back to such communities.

No one wants to spend the holidays without their lover, and this melancholic Christmas song covers that exact feeling. The original “Please Come Home For Christmas” was a 1960s R&B rendition by blues singer Charles Brown. While the Eagles' cover of the track became the most popular version, both are equally gut-wrenching yet beautiful. 

Sabrina Carpenter’s Christmas song “cindy lou who” takes heartbreak one step further by detailing the pain of watching your ex move on with someone new. As if breakups and loneliness weren’t enough during the holiday season, witnessing your lover date a new partner is pure torture. Sabrina packs all the pain and longing into this melancholy holiday hit.

This heartbreaking Christmas song describes a young boy growing up without a father, detailing its impact on his sense of self-worth. The little boy believes Santa has forgotten him, as he sends his Christmas lists/letters only to be met with nothing on Christmas morning. As the tragic lyrics go, “He's the little boy that Santa Claus forgot, and goodness knows, he didn't want a lot.”

“If We Make It Through December” by Merle Haggard details the harsh yet relatable reality of financial struggles during the holiday season. The narrator strives to give his daughter the Christmas she deserves, but after being laid off at his factory job, he can barely make ends meet for his family. He reveals through the lyrics, “And my little girl don't understand why daddy can't afford no Christmas here.”

Stevie Wonder's "Someday at Christmas" reminds us of the equality and suffering experienced around the world, even during “the most wonderful time of the year.” Rather than turning a blind eye, the song urges humanity to work toward peace and unity. As the lyrics go, “Someday at Christmas, there'll be no wars. When we have learned what Christmas is for, when we have found what life's really worth, there'll be peace on earth.”

“A Long December” by Counting Crows is a melancholic yet hopeful holiday track. It covers themes like loss, change, regret, and the belief that things will get better in the new year. The alternative rock song describes the human experience unlike any other.

Prince's emotional ‘80s ballad is perhaps one of the most heartbreaking Christmas songs out there. It describes the devastating loss of a lover mere days before Christmas. As its title suggests, the track talks of how lonely the holiday feels without the deceased partner.

Another song that deals with grief is “Red Water (Christmas Mourning)” by Type O Negative. This gothic metal Christmas song is as haunting as it is melancholic, detailing the aftermath of loss around the holidays. The track begins with some of the most devastating lines and clever play on words: “Wake up, it's Christmas mourn. Those loved have long since gone. The stockings are hung, but who cares? Preserved for those no longer there.”

Warning: if you have a tragic “the one that got away” love story, don’t listen to this song, as it might trigger some heavy grief. However, if you want to torture yourself this Christmas, give it a go. The song details two ex-lovers running into each other at the grocery store on Christmas Eve. They’re both shocked to see one another, and as they get to talking, they realize they're clearly still in love. Despite their lingering feelings, they part ways and return to the unfulfilling lives they've moved on to.