5 Holiday Songs for the Sad Santa Types

Christmas music tends to generally fall along the merry and bright end of things. Songs of joy and happiness fill the airwaves, and everyone feels that fond glow of happiness nestled all snug in the soul.

But it’s worth remembering — nay, embracing — the more melancholy sounds of the season. Although the focus upon glad tidings and cheer can feel a bit relentless, there is a sadness inherent in Christmas. (Look no further than the minor key masterpiece “A Charlie Brown Christmas,” which reminds children that those twinkling lights could just as easily be glistening tears.)

Perhaps a loved one is not with you to celebrate Christmas, or there are painful memories associated with the holiday, or you’re unable to be with family for one reason or another. The gloom can manifest itself any number of ways, and fortunately, there are a whole crop of songs ideally suited to help you work through any less-than-holly-jolly feelings. Here are five songs, in no particular order, to get you started on your sad Santa playlist — you might need to spike the egg nog to make it through ’em all.

Mindy Smith, “Santa Will Find You”
Found on Smith’s 2007 album, My Holiday, this gently strummed and sweetly sung ode to the power of belief has always been a go-to for some easy Christmastime tear-jerking. Something about the way Smith tremulously sings, “With the spirit of Christmas/You’ll never be lost/If you truly believe in your heart” near the climax, never fails to pierce the soul.
Everly Brothers, “Christmas Eve Can Kill You”
You might expect the Everly Brothers to have plenty of warm and fuzzy Christmas tunes in their arsenal — and they do; 1962’s Christmas with the Everly Brothers and the Boystown Choir is a keeper — but this track from 1972’s Stories We Can Tell is a bruising reminder to be grateful, as the narrator speeds past a homeless man hitchhiking in the cold: “The sound of one man walking through the snow can break your heart/And stopping doesn’t help, so on I’ll go.”
Wham!, “Last Christmas”
From cool to cheesy and back around again, this slice of ’80s pop nostalgia, released as a single in 1984 and on the duo’s final album, Music from the Edge of Heaven, in 1986, is firmly fixed in most holiday playlists. But how many have really considered what George Michael and Andrew Ridgeley are sharing here? “I’m hiding from you and your soul of ice/My God, I thought you were someone to rely on,” Michael croons, sketching a bombed-out husk of a relationship amid all the tinsel.
Simon & Garfunkel, “7 O’Clock News/Silent Night”
This brief song is 53 years old, but no less harrowing for the passage of time. Paul Simon and Art Garfunkel sing a simple, lovely version of “Silent Night” over piano, as Charlie O’Donnell narrates a simulated newscast. This track, the final song on 1966’s Parsley, Sage, Rosemary and Thyme, prefigures the notion of a mashup by several decades, and perhaps most troubling of all, could easily be updated for the 21st century and sacrifice none of its potency.
Dolly Parton, “Hard Candy Christmas”
Falling as it does toward the end of the year, Christmas is often a time for reflection upon the months that have just passed and the months that lay ahead. Dolly Parton acknowledges that transitional feeling in this 1982 gem, reeling off a litany of changes that may come to pass, before finding a silver lining in the gloom: “Lord, it’s like a hard candy Christmas/I’m barely getting through tomorrow/But still I won’t let/Sorrow bring me way down.”