#16: 5 POUND BOX OF MONEY by Pearl Bailey

Most funny Christmas songs are stupid.  Grandma got Run Over By A Reindeer immediately comes to mind.  But this song, by President Nixon’s Ambassador of Love (it’s true, look it up) is fantastic.  It’s hard to find anything out about the creation of the song, but ASCAP credits Bailey and someone named Jack Barker with writing it.

Further listening: Bob Dylan’s, “Must Be Santa” is in a similar vein, as is Louis Armstrong’s “Zat You, Santa Claus?

#15: River by Joni Mitchell (1971)
Most Christmas songs are at least partly joyous.  Not so, Joni Mitchell’s “River,” which appeared on her “Blue” album, the one most consider to be her best.  (They’re wrong, her best was Court and Spark.  But it’s a close call.)
Like many songs on this list, it’s about the end of a relationship at Christmastime, and it incorporates something that sounds vaguely like a more traditional Christmas song (in this case, Jingle Bells).  To fans of 1970s folk, it’s a huge song—covered by many—but lots of younger people probably know it as the song Robert Downey, Jr., sang in Ally McBeal.  Wait, did I say “younger people?”  I can’t believe Ally is over 20 years old.

Further listening: Another folk(ish) Christmas song worth hearing is New Year by Death Cab for Cutie,

Covers: Lots, but let’s kick it off with Iron Man and follow up with Judge Green…

#14: Merry Christmas (I Don’t Want To Fight Tonight)-The Ramones (1987)

The masters of the under-three-minute punk rock song fashion a Christmas song where the holiday is used as an excuse to let a bad relationship continue for just one more night.  “Christmas ain’t the time for breaking each other’s heart,” Joey sings, “Merry Christmas, I don’t want to fight tonight with you.”

The song never even made the charts.

Further listening: Christmastime, by Smashing Pumpkins.  They ain’t punk, but they’re close.

Covers: It’s the Ramones, so of course there are tons…Here’s a few good ones.

#13: De La Soul, Millie Pulled On Santa (1991)

From the album that many believe killed off De La Soul (ironically titled, De La Soul is Dead), this is a funny and shocking story about sexual abuse that goes into pretty excruciating detail, telling a story similar to Pearl Jam’s, “Jeremy.”  A kid gets pushed to the point of no return, and uses a gun to get justice.  Interesting non-Xmas side note: Atmosphere made a part two of this song, “Millie Fell off the Fire Escape.”

Millie had a fucked up life. 

Further listening: There’s not too many Christmas tragedy songs that are at this level.  But there are some violent ones, like Mr. Lif’s “Santa’s Got a Muthafuckin Uzi.”

Covers: See the Atmosphere sequel described above, and Company Flow’s instrumental “Suzy Pulled A Pistol on Henry.”

#12: If We Make It Through December-Merle Haggard (1973)

There are hundreds of country Christmas albums, and thousands of “original” country Christmas songs that really are just maudlin, tired treacle.  But Haggard’s If We Make It Through December is not one of them.  It’s a true workingman’s tune, from his incredibly depressing (but still awesome) record, Merle Haggard’s Christmas Present.  As you might guess from the song, it’s about a poor family struggling to get through the holidays.  It hit #1 on the Billboard charts.

Hit the tag below labeled, “G.O.A.T.: Greatest of All Christmas Tunes” to see more of my top 20 original Christmas songs!

Further listening: Please Daddy (Don’t Get Drunk This Christmas) by The Decemberists.

#11: Do They Know It’s Christmas? (1984) – Band Aid

It’s treacle, it’s tripe, it’s sentimental garbage…But you know all the words, right?  Written by Bob “Boomtown Rats” Geldof—a one-hit wonder band known mostly to a few fans of obscure British New Wave—and Midge “Thin Lizzy” and “Ultravox” Ure—bands known even fewer people, this “benefit song” became the best-selling single of all time.  And it was recorded in a day.  One day.  Unlike the bastard son it inspired, Michael Jackson and company’s “We Are the World,” which had much more star power but, in the end, was not nearly as good a song.  Although, admittedly, Bob Geldof himself has called this song the worst he ever wrote.  (Hm.  Really?  Not “Up All Night”?)  And to think, the only reason they made an original song (instead of just covering a traditional Christmas tune) was so that they wouldn’t have to pay royalties, which would (quite literally) take food out of the mouths of starving babies.
do they know its christmas all the artists
There were rumors, including this hilarious video by Spitting Image, that the artists only appeared because Bob Geldof threatened to release the names of people who didn’t help out…

The gang-bang-for-charity approach was also the inspiration for 1985’s series of Live Aid concerts.  But most importantly, it inspired one of Sam Kineson’s best jokes: “If you’re starving in Africa, move where the food is.”

The song made over $8 million for children starving in Ethiopia.  It featured Sting (of the Police), Duran Duran, Boy George and Culture Club, Spandau Ballet, Paul Young (who got to lead off the track), Phil Collins, Marilyn, Kool & The Gang, Bono and Adam Clayton (U2), The Boomtown Rats, Bananarama (perhaps the best-named girl band of all time), Glenn Gregory (Heaven 17), Chris Cross, George Michael, Status Quo, Paul Weller and Jody Watley.

Further listening: Uh…The B-side has messages from David Bowie and the dude from Frankie Goes to Hollywood.

Covers: There were several follow-up Band Aids for different charities, but they’re not worth your time.  Instead, check these out:


Related Posts

About The Author