I’m not feeling especially excited about the holidays this year, and I suspect I’m not the only one. Sometimes the onslaught of forced cheer in December is overwhelming (I recently had a near meltdown in the Target checkout line as “Simply Having a Wonderful Christmas Time” wormed its dreadful way into my brain), and in those moments, listening to sad holiday music can be wonderfully cathartic. Whether you’re missing far-flung friends and family, grieving the loss of a loved one, or feeling generally exhausted by the trials and tribulations of 2020, this wistful, 100 percent Texan playlist is for you. Listen below, or follow us on Spotify, where you can also find a bigger Texas Monthly holiday playlist.
“Christmas Makes Me Cry” by Kacey Musgraves
This one goes out to the homesick Texans who’ve had their travel plans scuttled by the coronavirus. “Another year gone by, just one more that I / I couldn’t make it home,” Musgraves croons. Her entire Christmas album is fantastic, including a duet with Willie Nelson (“A Willie Nice Christmas”).
“Pretty Paper” by Willie Nelson
This beloved, poignant tune was inspired by Frankie Bierton, a disabled man who sold holiday wrapping paper outside a Fort Worth department store in the fifties and sixties. Nelson, who at the time was a door-to-door vendor of vacuums and encyclopedias, often saw Bierton and wondered about his story. In an episode of Texas Monthly’s One by Willie podcast last month, Lumineers front man Wesley Schultz said the song brings him comfort whenever life is less than perfect: “It gives me this feeling like I’m not alone.”
“River” by Lera Lynn
Haunting and beautiful, Joni Mitchell’s “River” might be the greatest sad holiday song of all time—if not one of the greatest melancholy songs, period. Her narrator is lamenting a breakup, but the lyrics apply equally well to any tough situation. Houston-born Lera Lynn’s slow, stripped-down cover more than does it justice. Other than subbing Mitchell’s piano melody for stripped-down guitar, she stays faithful to the original, with vocals that sound uncannily like Joni herself.
“Christmas Time Is Here” by Khruangbin
Slowed down and chilled out, Khraungbin’s mellow rendition of the 1965 classic from A Charlie Brown Christmas invites you to let your worries drift away. Lee Mendelson, who cowrote the song with Vince Guaraldi, died on Christmas Day last year.
“Ring Them Bells,” by Sarah Jarosz
Okay, so it’s not technically a holiday song, but “Ring Them Bells,” written by Bob Dylan in 1989, has a quiet reverence to it that feels right for this time of year. Jarosz’s plaintive vocals and guitar picking are at once celebratory and mournful, and it’s hard not to be moved when she sings, “Ring them bells for the blind and the deaf / Ring them bells for all of us who are left.”
“Christmastime Is Coming” by Lightnin’ Hopkins
The Centerville native and legendary bluesman croons about Santa Claus and confesses that “I lied to my woman” in this 1964 tune, recorded in Houston.
“Lonely Lonestar Christmas” by Aaron Watson
There’s something about a song that pairs a catchy, cheerful tune with lyrics that are depressing as all get-out. The narrator of this song finds himself drinking alone at 1 a.m. on Christmas, missing his ex-lover—but he’s snapping his fingers and laughing at himself too.
“In the Bleak Mid-Winter,” by Shawn Colvin
The Austin-based singer-songwriter’s version of this classic carol, based on a poem first published in 1872, reminds listeners that joy can arrive when you least expect it. It’s even more powerful when you learn about the many demons that Colvin has overcome.
“If We Make It Through December” by Wade Bowen and Cody Canada
Merle Haggard’s 1973 hit gets an uptempo treatment from Bowen and Canada, who hail from Waco and Pampa, respectively. Despite the dark subject matter, it’s hard not to tap your toes to this catchy, rollicking melody.
“Merry Christmas From the Family” by Robert Earl Keen
It’s one of his biggest hits for a reason, y’all. We highly recommend listening to a live version of this celebration of family dysfunction, so that you can join the crowd in hooting, hollering, and singing along to every chorus.
“Lonely Christmas Call” by George Jones
Jones, whom this magazine once called “the world’s greatest country singer,” delivers a honky-tonk lament for the ages.
“Hard Candy Christmas” by Molly Burch
Abilene composer Carol Hall wrote this song, which Dolly Parton first released in 1982 as part of the soundtrack to The Best Little Whorehouse in Texas. Parton later explained that the phrase “hard candy Christmas” refers to being so poor that the only treat you can afford for the holidays is a piece of hard candy. Austin singer-songwriter Molly Burch’s version is downtrodden but hopeful, especially when she sings, “I’m barely getting through tomorrow / but still I won’t let sorrow bring me way down.”