The saddest Christmas songs ever?

Aimee Mann, shown during her 2011 holiday concert in Los Angeles, sings Jimmy Webb's melancholy "Whatever Happened to Christmas."

By Randy Lewis

Nov. 28, 2012 12 AM PT

“It’s the most wonderful time of the year,” says one of the most popular songs of the season. Yet good cheer isn’t what everyone experiences during the holidays. With that in mind, Pop & Hiss hoped to compile a list of the saddest yuletide songs ever recorded.

We can’t claim these are definitively the saddest, because there are so many more available to choose from. Some are holiday standards, others may be less familiar because they typically don’t show up on shopping mall playlists and those 24/7 holiday-music radio stations. So here are two dozen of our favorite holiday downers, in alphabetical order:

Elvis Costello & the Chieftains, “The St. Stephen’s Day Murders.” Costello collaborated with Chieftains leader Paddy Moloney on this macabre tale referencing the first Christian martyr and a less-than-idyllic holiday gathering of relatives: “For that is the time to eat, drink and be merry/Til the beer is all spilled and the whiskey has flowed/And the whole family tree you neglected to bury/Are feeding their faces until they explode.” From the Chieftains’ 1991 album “The Bells of Dublin.”

Fear, “F— Christmas.” L.A.’s notorious punk outfit weighed in on what’s supposed to be the happiest season of the year in its jolting 1982 single in which singer Lee Ving wails: “Don’t despair, just because it’s Christmas/Children, they’re all so gay at Christmas/All the children on the street/Hope they get something good to eat/But for me it’s not so great.” Then the world explodes.

Rosie Flores, “My Christmas Tree Is Hung With Tears.” This bluesy ode to a departed love tugs hard on the heartstrings. Her album also includes an inspired minor-key arrangement of “Blue Christmas,” a twist that serves the mournful lyric beautifully.

Judy Garland, “Have Yourself a Merry Little Christmas.” The “merry” in the title couldn’t sound more disillusioned than in the 1944 version by pop’s original diva.

Vince Gill, “It Won’t Be the Same This Year.” The country-bluegrass singer applies his high lonesome voice to a song written after the death of his brother: “It’s time to pack our bags and hit the highway/And head on out for Christmas holiday/I’ll fall apart when I pull in the driveway/It’s my first time home since brother passed away.”

Vince Guaraldi Trio, “Christmastime Is Here.” There are words to this cornerstone song from the 1965 TV special “A Charlie Brown Christmas,” but Guaraldi’s original instrumental arrangement communicates all you need to know about the glum reverie inherent in the season for many people.

Merle Haggard, “If We Make It Through December.” An unemployed blue-collar worker’s angst comes through powerfully in Haggard’s 1973 country classic: “I got laid off down at the factory/And their timing’s not the greatest in the world/Heaven knows I been workin’ hard/I wanted Christmas to be right for daddy’s girl.”

The Kinks, “Father Christmas.” Kinks’ lead singer and songwriter Ray Davies has always taken the side of the little guy, and that’s who he salutes in the band’s punk-infused 1977 holiday single: “Have yourself a merry, merry Christmas/Have yourself a good time/But remember the kids who got nothin’/While you’re drinkin’ down your wine.”

Darlene Love, “Christmas (Baby Please Come Home).” A girl begs for her love to return in this gem from Phil Spector’s celebrated 1963 collection “A Christmas Gift for You.” As energetic and bright as Spector’s production shines, you can’t help but be moved by the yearning in Love’s voice as she sings “Please…please…please” to her absent objet d’amour.

Shelby Lynne, “Xmas.” On this track from her 2010 album “Merry Christmas,” the soulful country singer-songwriter goes for deep blues, wasting no time communicating what the season brings up for her: “Christmas makes me sad/That I’m being bad/Holiday cocktails make me forget/The gift that Daddy never opened.”

Aimee Mann, “Whatever Happened to Christmas.” Jimmy Webb’s song showed up on Mann’s 2006 album “One More Drifter in the Snow,” which was less a conventional holiday album than a genuine exploration of the emotions of the winter season. Mann sings, “Remember the sights and the smells and the sounds/Remember the cheery cards/Remember how love was all around/Whatever happened to it all?”

Chuck Mead, “Will Santa Come to Shanty Town?” Country boy Eddy Arnold tapped his hardscrabble youth when he co-wrote this song questioning whether Santa would visit his underprivileged neighborhood: “He didn’t stop last Christmas Eve/Doesn’t he know we live here?/Will my mommy have to paint my toys -- The way she did last year?” Roots rocker Mead has recorded a bouncy but still melancholy new version for 2012.

Joni Mitchell, “River.” The Canadian singer-songwriter’s 1970 song about a holiday breakup has become a contemporary classic, turning up on dozens of other artists’ seasonal albums. Still, nobody tops Mitchell’s sense of loss and hurt as she sings, “I’m so hard to handle/I’m selfish and I’m sad/Now I’ve gone and lost the best baby/That I ever had/I wish I had a river I could skate away on.”

Tracy Newman, “Mama, I Know You Ain’t Santa.” TV comedy writer-turned-songwriter Tracy Newman has crafted a gentle tearjerker (Dolly Parton said it made her cry) saluting a single mother who has to pull double duty as Santa Claus for her kids: “Billy don’t know you ain’t Santa/How could he -- he’s only 2?/Billy don’t remember Daddy/But mama, you and I do.”

Over the Rhine, “All I Ever Get for Christmas Is Blue.” Ohio husband-wife duo Linford Detweiler and Karen Bergquist included this on their brilliant 2007 holiday album “Snow Angels.” Bergquist lays out the feeling of anyone who ever wanted to stay in bed and shut the world outside as she sings, “Strings of lights above the bed/Curtains drawn and a glass of red/All I ever get for Christmas is blue.”

Buck Owens, “Blue Christmas Lights”/”It’s Christmas Time for Everyone but Me.” The achingly beautiful steel guitar work of Buckaroos member Tom Brumley underscores the soul-deep pain in two songs from Owens’ sterling 1965 album “Christmas With Buck Owens and His Buckaroos.” Owens borrows the melody of his own hit “Crying Time” for “It’s Christmas Time for Everyone but Me,” singing, “All of everything is nothing dear without you/And it’s hard to live with just a memory/For I need your love to give each day a meaning/Oh it’s Christmastime for everyone but me.”

Elvis Presley, “Blue Christmas.” Billy Hays and Jay W. Johnson’s downcast tune has been recorded hundreds of times, most famously by Elvis for his 1957 Christmas album. The heartache is amplified by the Jordanaires’ swinging “ooh-ooh-oohs” behind the King’s voice.

John Prine, “Christmas in Prison.” The acclaimed Chicago singer-songwriter vividly conjures what the season might look like through the eyes of someone separated from his loved ones while doing hard time: “The searchlight in the big yard/Swings round with the gun/And spotlights the snowflakes/Like the dust in the sun.”

Mindy Smith, “My Holiday.” The Long Island-reared, Nashville-based singer-songwriter wrote an ode to her artificial tree in the title track from her exquisite 2007 holiday album. Dissonant chords and an unconventional melody add to the melancholy feeling behind her outwardly celebratory lyric: “Somebody’d say this tree’s not real/’Cause it stands there every year/But it makes my holiday feel like Christmas/When Christmas time is here.”

Sufjan Stevens, “Did I Make You Cry on Christmas Day? (Well You Deserved It).” The prolific indie rocker has a lot to say about the holidays. If his 42-song box set “Christmas” from 2006 wasn’t enough, he’s just released “Silver and Gold,” a five-CD set with 58 additional yuletide songs. This one from his 2006 collection looks at a downward-spiraling relationship that gets more dysfunctional during the holidays. “This time of year you always disappear/You tell me not to call… And when the door is closed you’re wearing different clothes/Or hiding in the paper, pretending not to hear.”

Barbra Streisand, “I’ll Be Home for Christmas.” This World War II-era number first came to fame with Bing Crosby’s 1943 version, capturing the sadness of a soldier serving far from home at Christmas. Streisand delivered a gorgeous rendition on her 2001 album “Christmas Memories.”

Dwight Yoakam, “Santa Can’t Stay.” From Yoakam’s 1997 album “Come on Christmas,” this rockabilly-steeped big-band arrangement sets the scene of the holiday for a split family: “Mama says Santa can’t stay/Says she told him that twice yesterday/Then a car just like Dad’s pulled out and drove away/As mama said ‘Santa couldn’t stay’.”

The Youngsters, “Christmas in Jail.” A 1956 doo-wop-based R&B; chesnut about a nitwit who drinks and drives on Christmas Eve, this one is more lighthearted than the rest: “ ‘Merry Christmas, happy new year,’ they’re singing down the street/While everybody’s havin’ Christmas turkey/They give me bread and water to eat.”

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Follow Randy Lewis on Twitter: @RandyLewis2