If hip-hop has a Constitution, buried somewhere within its depths, there is surely a clause stipulating that if you reach a certain echelon of success, you have to make a Christmas song. Part of why the “Christmas Rap Song” trope is so enduring is that it allows rappers to use holiday cheer as a weapon to deflate the overblown machismo and bluster that often serves as the backbone of the gangster rap persona while also indulging in it––what is a rapper like Jim Jones gate-crashing your Holiday party doing if not injecting danger into a holiday that in many ways defines our nation’s sanitized, capitalist impulses?
There were a few Christmas rap songs that I wanted to include on this list but, regrettably, have not been released on vinyl–– “Ghostface Xmas” and The Ying and the Yang of the Holidays, I’m looking at you two––but if you want to amuse your little cousin and horrify your parents through playing vinyl this holiday season, this here list is a good primer. It would be unfair to say these tracks have not aged well, because they were not meant to be good in the first place––Snoop Dogg was under no illusions that “Santa Claus Goes Straight to the Ghetto” was not up to snuff with his contributions to Dr. Dre’s The Chronic––but that doesn’t mean they aren’t all charming, original, and funny as hell.
A Holiday Gift From Vinyl Me, Please To You
Vince Guaraldi Trio
A Charlie Brown Christmas (LTD. to 1500) (Pressed at QRP)
Christmas In Soulsville (LTD. to 1000)
The Molly Burch Christmas Album (LTD. to 300)
Vince Guaraldi Trio
A Charlie Brown Christmas (LTD. to 1500) (Pressed at QRP)
Eazy E - 5150 Home 4 tha Sick EP
Fun fact: Eazy-E’s first post-N.W.A. release ends with what might be the most random song of all time: “Merry Muthafuckin’ Christmas,” Eazy’s redux of “Jingle Bells” that was produced by a pair of white dudes from Denmark and featuring the first recorded raps from a 17-year-old will.i.am. Like, that will.i.am, the one from the Black Eyed Peas. Last year, the track was re-released as a festive, red seven-inch for Record Store Day, coupled with the amazingly named song “N––az My Height Don’t Fight.”
OutKast - “Player’s Ball” 12”
Another fun fact: OutKast’s first commercially released single was “Player’s Ball,” a soulful Christmas rap featuring Southern-fried sleigh bells and a bassline smoother than an eggnog oil slick. Though it originally appeared as part of A LaFace Family Christmas, a Christmas compilation put together by Babyface and L.A. Reid’s label LaFace (bet you didn’t see that one coming), the song found a life of its own––especially after the release of its music video, which just happened to be directed by goddamn Puff Daddy. “A lot of people don’t realize I directed OutKast’s first video,” said a self-satisfied Puff while swilling Ciroc in the documentary The Art of Organized Noise. “I realize it because I make sure I tell my kids [about it] every day.”
Before you render judgment, just watch the music video for “Santa Claus Goes Straight to the Ghetto,” in which Snoop Dogg dresses up as Santa Claus and flies a ‘64 Chevrolet through the night sky with Daz Dillinger, Nate Dogg, Bad Azz, and Tray Dee in tow. Released in 1996, Christmas on Death Row might lean heavily upon the Death Row B-Team––Danny Boy, the label’s in-house semi-anonymous R&B hookman, is asked to carry way too much weight here––but the album’s worth purchasing for the cover alone, featuring the iconic Death Row Records mascot dressed up in a Santa Claus suit.
With all due respect to Jim Jones’ A Dipset Xmas, this holiday-hop effort from Master P’s egregiously prolific No Limit Records might be the most genuinely enjoyable batch of Christmas gangster rap ever to be released. The 1994 record succeeds for the reason that most of the label’s records from its pre-New Orleans days succeeded: the label’s unrelenting dedication to mob music, and Master P, who swoops in to resuscitate the track with his weird charisma whenever the energy might threaten to drop. The title track is a genuinely great rap ballad, while “Jackin’ for the Holidays” finds Master P Grinchily jacking for beats, and “Christmas in the Ghetto” manages to be both sad and goofy at once.
Kurtis Blow - “Xmas Rappin” 12”
Much like OutKast, Kurtis Blow’s debut single was none other than a Christmas song. But unlike OutKast, the bassline for Kurtis Blow’s 1979 holiday hit sounds suspiciously like that of Queen’s “Another One Bites the Dust,” released just a year later. Kurtis interrupting some lame-o saying, “Twas the night before Christmas” to say, “Hold it now… hit it!” would eventually be sampled by everyone from the Beastie Boys to J. Dilla to Dream Theater, because Kurtis Blow was cool as hell like that. I used to play this song a LOT on my college radio station, but never actually during Christmas, because that was what the powers that be at my state-controlled mind-control-camp-cum-liberal-arts-“university” would have wanted.
Jim Jones — Ballin on Xmas (B-side of “We Fly High (Remix)” 12-inch)
Oh, if only Jim Jones’ Christmas album A Dipset Xmas were on vinyl! What a joyous list this would be. Though the Dipset capo’s label Koch Entertainment made the perilous mistake of never releasing “Ballin’ on Xmas” as a single––there’s no way a Christmas song featuring Stack Bundles wasn’t going to Number One––they did slap the track onto the B-side of the “We Fly High (Remix)” 12-inch. If you’ll recall, that remix featured Baby, Jermaine Dupri, T.I., Young Dro, and none other than Puff Daddy… WHO ALSO DIRECTED THE MUSIC VIDEO FOR OUTKAST’S “PLAYER’S BALL.” Puff Daddy, truly a titan of tangential connections Christmas rap singles.
David Banner - “The Christmas Song” 12”
David Banner is a hero for many reasons, but turning “Carol of the Bells” into a crunk song is definitely one of them (the Ying Yang Twins tried this same trick a few years later, to an altogether lesser effect). The track showed up on both Banner’s MTA2: Baptized in Dirty Water album, as well as the flip side of his “Crank It Up” single, so your options for obtaining this track on vinyl are essentially endless.
Leave it to Rick Rubin and Run DMC to cook up the first massive Christmas rap song––which makes sense, given that they were the guys who cooked up many of the first truly massive hip-hop moments. The track appeared, alongside such non-hip-hop entities as Bruce Springsteen and Eurythmics, as the lone hip-hop contribution to the A Very Special Christmas compilation back in 1987, which featured cover art by Keith Haring because the 80’s were cool like that.
Stones Throw impresario Peanut Butter Wolf is a known Christmas enthusiast, so it only makes sense that he’d put together a compilation featuring rare, offbeat, and undeniably snappin’ Yuletide tunes. My personal favorite is Bruce Haak’s “I Like Christmas,” in which the synth and vocoder pioneer––and extremely early Def Jam signee––amiably vocodes his way through a ditty about, uh, why dude likes Christmas. There’s also 69 Boyz and Quad City DJs’ “What You Want for Christmas,” which is the best Miami Bass Christmas song ever of all time.
Treacherous Three - “Santa’s Rap” 12”
The name of this Christmas rap single is a slight misnomer––what actually transpires is Santa starts rapping, only to get interrupted by the Treacherous Three who complain about what a tightwad he is, rob his ass, and tell him that if he comes back to their neighborhood next year he’ll get killed. The next verse involves Treacherous Three complaining about their presents to their parents. The track goes on for six amazing minutes, using wicked humor to slip in some trenchant commentary about the class divisions highlighted by the most wonderful time of the year.