34 of the Best, Wackiest, and Weirdest Christmas Songs

Judy Garland, "Have Yourself a Merry Little Christmas"

It's hard not to tear up when Judy Garland sings "Have Yourself A Merry Little Christmas" in the Vincente Minnelli musical Meet Me in St. Louis. The song distills the melancholia that can settle on even the jolliest soul during the holiday season otherwise known as #SadGirlFall and #CozyGirlWinter. While the words are cheerful (merry is literally in the title), Garland's performance is breathtaking and, yes, heartbreaking. Since its 1944 debut, the song has become a Christmas classic covered by contemporary greats like Sam Smith, Christina Aguilera, and Frank Sinatra, though few have surpassed Garland's tear-jerking performance.

Bessie Smith, "At the Christmas Ball"

It's no fun to get the blues at Christmas, unless Bessie Smith is singing them. The legendary blues singer gave a Christmas gift to the world with her song, "At the Christmas Ball." She recorded the song two years after she became a superstar thanks to her hit album Down-Hearted Blues. The song is a hearty ode to the season and all its merrymaking, with Smith offering sage advice like, "If your partner don't act fair, don't worry there's some more over there" and reminding listeners that "Christmas comes but once a year, and to me it brings good cheer/And to everyone who likes wine and beer." This is one of the best bittersweet Christmas songs of all time, and should be at the top of your holiday Spotify playlist.

John and Yoko, The Plastic Ono Band with the Harlem Community Choir, "Happy Xmas (War Is Over)"

It's hard to believe this antiwar classic is almost 50 years old (!), but its resonance has not dimmed even in the slightest during that time. When John Lennon and Yoko Ono were engaging in various protest activities—think their late '60s bed-ins—they were also making beautiful and meaningful music designed to reach the masses, but also to convey a serious message. Layering Christmas wishes with a pointed desire for peace, the couple took aim at the Vietnam War and encouraged people to think about the greater global context at a time of sometimes ignorant celebration and indulgence.

The Pogues, "Fairytale of New York"

According to The Pogues' lead singer, Shane MacGowan, this anti-Christmas anthem started out as a bet. We love a good anti-Christmas anthem. Singer, songwriter, and producer Elvis Costello bet MacGowan he couldn't write a Christmas duet to sing with the band's bass player (and Costello's future wife) Cait O'Riordan. Costello may have lost his wager, but the world got "Fairytale in New York," a wistful song for anyone who has been lonely on Christmas Eve—even those in, "in the drunk tank."

Bing Crosby, "White Christmas"

Irving Berlin penned "White Christmas" for the classic Christmas movie Holiday Inn, and Bing Crosby delivered a beautifully memorable, if slightly mournful, take on the tune. As an aside, if you haven't seen Holiday Inn, you must. Crosby got a second shot at the song on the set of White Christmas, where he knocked it out of the park (again). Since then the song has become a standard, performed by artists ranging from Frank Sinatra to Jim Carrey and, more recently, Michael Bublé (featuring Shania Twain). The nostalgic song is so popular that it holds the Guinness World Record as the best-selling single of all time.

Run-DMC, "Christmas in Hollis"

The 1987 Special Olympics charity album, A Very Special Christmas, had some incredible contributions from A-list artists like Madonna, Whitney Houston, Bruce Springsteen, and Stevie Nicks. But their songs (mostly covers) were all overshadowed by the standout track "Christmas in Hollis" from upstarts Run-DMC. Of course, the hip hop group is behind smash hits like, "It's Tricky" and "Its' Like That." The Christmas song, based on the neighborhood of Hollis, Queens, sampled Clarence Carter's "Back Door Santa" (more on that below) and sounded unlike any other Christmas tune out there. While Run-DMC weren't the first group to make a Christmas rap song (that honor goes to Kurtis Blow's "Christmas Rappin'"), they made a memorable, honest, and fun song. Or, as DMC himself put it, "The beat is dope. The flow is dope. The rhymes are dope." Plus, the video featured his mom.

Wham!, "Last Christmas"

Look, the holidays aren't a great time for everyone—especially when images of happy families and couples are continually thrust in your face, like, literally everywhere. Never mind though, because the '80s heartbreak stylings of Wham! will keep you comfort. From the attempts to show a brave face ("Tell me baby / Do you recognize me?") to the devastating letdown ("Well, it's been a year / It doesn't surprise me"), it's a full picture of romantic ups and downs. It may have been beaten to #1 in the U.K. by "Do They Know It's Christmas," but it's still number one for all you lovelorn.

Big Star, "Jesus Christ"

If you're looking for a Christmas song that you can play all year round—or just a jam that to gently remind you of what believers call "the reason for the season"—look no further than Big Star's "Jesus Christ." The song was an incongruous presence on the highly influential band's summery third album, Third/Sister Lovers, featuring angels from the realms of glory and stars shining brightly on King David's city. There seemed to be no particular reason that the '70s Nashville rockers included an ode to the nativity in the middle of their final album, but we're sure glad they did.

David Bowie and Bing Crosby, "Little Drummer Boy/Peace on Earth"

Traditionally, "Little Drummer Boy" is known as one of the most interminable Christmas carols. But then came David Bowie and Bing Crosby, who transformed the drudgery into a joyous and uplifting song. The unlikely pairing came about thanks to Bowie's mom, who loved Bing Crosby and convinced her son to perform on Crosby's 1977 TV special, Merrie Olde Christmas. Bowie loved his mom but drew the line at singing the dreaded "Little Drummer Boy," so some quick-thinking writers whipped together an entirely new song. The tune was called "Peace on Earth" and Bowie sang it in perfect counter-harmony to Crosby's "Little Drummer Boy." The result is beautiful.

Darlene Love, "Christmas (Baby Please Come Home)"

In case you didn’t already know, Darlene Love is basically the queen of Christmas (sorry Mrs. Claus!). Just ask David Letterman, who had an annual tradition of inviting her on his show every year to perform this hit. Plenty of artists have covered it over the years, but there’s nothing like the original.

The Carpenters, "Merry Christmas Darling"

This song is a must for any chilled-out Christmas playlist. It’s the ideal soundtrack for unwinding in the family room bathed in the glow from the Christmas tree after all the holiday hoopla is done and you're conked out on the couch in a tryptophan coma. Just take a few minutes to enjoy this song while you bask in the spirit of the season.

Mariah Carey, "All I Want For Christmas is You"

The opening notes of Mariah’s 1994 hit spread more Christmas cheer than every mall Santa combined. It’s nearly impossible not to smile (and do a little dance) whenever it comes on. Some might say it gets overplayed every year (impossible), but there’s nothing like the excitement you feel the first time you hear it every holiday season.

Sufjan Stevens, "Christmas Unicorn"

Sufjan Stevens is clearly a Christmasholic: He's created a cottage industry of albums with all-Christmas songs featuring multilayered and gorgeously complex sounds and whimsical lyrics. In 2012, he released Silver & Gold: Songs For Christmas, which had a whopping 58 songs spread across five EPs. This song. One of the more interesting tracks in the collection even involves a Christmas unicorn with a beard and a pagan tree because why not.

Fat Daddy, "Fat Daddy (Is Santa Claus)"

This song by Paul "Fat Daddy" Johnson, Baltimore's self-anointed "300 Pound King of Soul," is featured on A John Waters Christmas, the eclectic holiday soundtrack curated by the apparently Christmas-loving director of Cry Baby and Pink Flamingos. Johnson hosted a radio hour back in the '50s and '60s, and inspired the, arguably, best character in Hairspray: Motormouth Maybelle. His ode to 'ole jolly St. Nick is a Christmas classic.

Beck, "The Little Drum Machine Boy"

It's not the holiday season until 808 beats begin to mingle with silver bells drifting through the air—that is, according to Beck's Christmas oddity, "Little Drum Machine Boy." The carol (?) appeared on the 1996 Geffen compilation Just Say Noël, which also featured a catchy tune from Sonic Youth called "Santa Doesn't Cop Out On Dope" and Aimee Mann and Michael Penn's "Christmastime."

Shonen Knife, "Space Christmas"

The Osaka-based band toured with Nirvana and the Breeders back in the '90s. They're still making music today. The grrrrl group is also influenced by the Supremes, the Ramones, and the Beach Boys. You can hear it all in their delightfully strange holiday song, "Space Christmas." The song, released in 1991, asks Santa to please bring a space ship while riding a "bison sleigh." If you think about it, honestly, bison are just as unlikely as flying reindeer. So it all makes sense. Right?

Brenda Lee, "I'm Gonna Lasso Santa Claus"

When Brenda Lee was just nine years old, she threatened, "I'm Gonna Lasso Santa Claus." Because why not? This merry tune offers a very bizarre lesson in Santa kidnapping, as Lee promises to "pop, pop Santa Claus with [her] water pistol gun." Unlike greedy Gayla Peevey, who wanted a hippopotamus all for herself, Lee's got a bit of a Robin Hood streak. In "I'm Gonna Lasso Santa Clause," she promises to "take his bags of toys and run and bring to all the kids who don't have none." This wasn't Lee's only Christmas tune, however. Four years later, at the age of 13, she became the first artist to record a little song called "Rockin' Around the Christmas Tree."

Akim and the Teddy Vann Production Company, "Santa Claus Is a Black Man"

Another gem from the John Waters Christmas compilation, "Santa Claus Is a Black Man," features songwriter Teddy Vann and his daughter Akim on the track.

AC/DC, "Mistress for Christmas"

There was no good reason for rock legends AC/DC to put out a Christmas song and yet we have "Mistress for Christmas." While some people might want a diamond ring or their two front teeth for Christmas (or, also, peace on Earth), AC/DC wants Santa to schlepp them a side chick. You know, to get funky with under the Christmas tree. Unfortunately, this is also a one way ticket to the naughty list.

Fat Les, "Naughty Christmas (Goblin in the Office)"

Set down your punch, because Fat Les is serving up a cautionary tale about drinking too much at an office Christmas party. This onetime strange supergroup consisted of Blur's bass player, Alex James, actor Keith Allen, and artist Damien Hirst. Pop singer Lily Allen provided extra vocals for background and Lisa Moorish sings about everything that could possibly go wrong after one too any eggnogs at work.