5 Saddest Christmas Songs If You’re Not Feeling The Holidays This Year

Each year, we crank up the Christmas tunes to celebrate the season with cheer, love, and togetherness. But not all holiday songs are filled with warmth and joy. Some tap into the more somber, bittersweet side of the season. If you’re in the mood for those “bluer” vibes, here are five Christmas songs that perfectly capture the more reflective moments of the holidays.

‘That Was the Worst Christmas Ever!’ (Sufjan Stevens)
Sufjan Stevens’ Songs For Christmas is filled with tracks that carry a sense of melancholy, and “That Was the Worst Christmas Ever” is no exception. The song begins with nostalgic memories of sledding, but quickly shifts to a darker side of the holiday. Stevens paints a picture of family conflict, singing, “Our father yells, throwing the gifts in the wood stove… My sister runs away, taking her books to the schoolyard.” The track wraps up with a hauntingly somber line: “Silent night, holy night / Silent night, nothing feels right.” It’s a raw take on the complexities of Christmas.

‘7 O’Clock News / Silent Night’ (Simon & Garfunkel)
In “7 O’Clock News / Silent Night,” Simon & Garfunkel brings a haunting twist to the classic Christmas carol by harmonizing over the soft melody while news of the day, delivered by newscaster Charlie O’Donnell, plays in the background. The 1966 news includes serious topics like the Civil Rights Bill dispute, the death of Lenny Bruce, and the ongoing Vietnam War.

Fast forward to 2019, and Phoebe Bridgers reimagines the song with Fiona Apple, featuring newscaster Matt Berninger. This version mentions modern issues like the Sackler family’s role in the opioid crisis and the Ukraine aid controversy. Both versions serve as stark reminders of the heavy events shaping the world, making them a jarring addition to any holiday playlist.

‘If We Make It Through December’ (Merle Haggard)
“If We Make It Through December,” a touching ballad about a father who loses his job and longs for brighter times ahead, was released by Merle Haggard in 1973. The song expresses optimism, but it also captures the sorrow and hardships that many families experience, particularly during the holidays. Haggard effectively conveys the emotional burden of attempting to support loved ones during difficult times with lyrics like “Heaven knows I’ve been working hard / I wanted Christmas to be right for Daddy’s girl,” making it a potent reminder of life’s difficulties throughout the holiday season.

‘Fairytale of New York’ (The Pogues feat. Kristie MacColl)
Don’t be fooled by the upbeat chorus—“Fairytale of New York” is a Christmas classic with a gritty story. Set in a New York City jail, Shane MacGowan and Kirsty MacColl sing about an Irish couple whose American dream falls apart. While the song has moments of hope, with dreams of Broadway and “rivers of gold,” it quickly shifts to a more somber tone. The raw lyrics, like “I could have been someone / Well so could anyone,” capture the pain of lost dreams and the struggles of life, making it a powerful holiday ballad.

‘Christmas Eve Can Kill You’ (The Everly Brothers)
The Everly Brothers’ narrative, “Christmas Eve Can Kill You,” centers on a desolate and lonely hitchhiker on a wintry Christmas Eve. He must confront the agonizing fact that if he were driving, he would most likely ignore himself as well as the cars that go by without stopping. As he muses, “The saddest part of all is knowing if I switched with him / I’d leave him stumblin’ ragged by the road,” the song encapsulates the tragedy of his circumstances and serves as a chilling reminder of how simple it is to overlook those in need during the holiday season.