If you truly want to be an expert in Christmas rap - and why the Hell wouldn't you? - then you've got to at least dip your toe into the world of Kevin & Bean. Who are Kevin and Bean? Radio show hosts on a station called KROQ; that's pretty much all I know. I guess they're like a morning "zoo crew" on a rock station or something? We don't need to care that much. The relevant part is that every year for decades, they've done Christmas compilation albums involving celebrities (the proceeds for which went to charity), and once in a very rare while, that includes rappers. Rappers doing exclusive Christmas rap songs for their albums.
Now, half these songs are comedy skits and gags, and rap being a part of their albums actually dates back to their very first, rare vinyl release in 1990. Specifically, "Rudolph the Red Nose Homeboy" by MC Frosty and Michael the Maintenance Man (the latter apparently being a recurring character on their radio show). But that's a joke song by a fake rap artist. There's more of that across these albums, and you probably have to be a fan of the radio show to really care about those. So I'm just going to focus in on the few releases with actual, legit Hip-Hop artists.
One of the break-out songs from these zany albums came in 1996: "Christmastime In the LBC" by Snoop and Friends. I'm sure you guys are all familiar with Death Row Records' infamous Christmas album with the pretty great Snoop Doggy Dogg Christmas song, "Santa Claus Goes Straight To the Ghetto." That was the same year, and a lot of people conflate the two; but this is something completely different. The idea is that it's a crazy, dark Christmas song by Snoop Dogg and the Death Row guys. But it's not. In fact it's Jimmy Kimmel (who was affiliated with KROQ at this point in time) doing an impression of him. It's pretty funny, actually. But yeah, it's a fake parody, so why bring it up here? Because the success of that song got Snoop to hook up with Kevin & Bean for real the next year. So in 1997, when Kevin & Bean released A Family Christmas In Your Ass, which compiled the best of their previously limited cassette-only albums onto a more mainstream CD, it also included new material like a a brand new, Snoop Christmas rap called "Twas the Night" with Nate Dogg. It's a song in that it has original music and all, but unfortunately it's more of a spoken word skit, with him reading his own version of the "Night Before Christmas" poem. But if you've seen it online or anything, yeah, this is where it's from.
Again, there's tons of these albums, and Kevin & Bean aren't rap guys, so there's not much of interest in most of them. There's big name celebs like Jon Stewart, Kevin Smith and the South Park guys doing skits, and songs by big rock bands like My Chemical Romance and Coldplay, but for Hip-Hop, this really isn't our territory. There are more joke songs, like Jimmy Kimmel doing an Eminem impression on "Stanley" and a funny fake Shaq song called "Holiday Heat." And sometimes they'll throw on a previously released rap song, like Outkast's "Player's Ball."
But the next original recording by an actual Hip-Hop group doesn't arrive until 2001's Swallow My Eggnog. Here, Cypress Hill turn up for "The Night Before Christmas," which yeah, you guessed it, is the same concept as Snoop and Nate's except it's full of marijuana references. The production's cool, but overall it's pretty lame, full of predictable jokes like "I still got you ho ho hoes." Of interest if you're a fan of the group, though.
Afroman also does a song on Swallow My Eggnog, and no it's not one from his Jobe Bells Christmas album. It's an original one called "Afroman's Christmas Joint." It's pretty short, but he's rapping over a beat with heavy sleigh bells on it. I don't really rate Afroman, but it's about on par with anything else he's done.
Finally, we come to the most legit and obscure one. 2006's Super Christmas. It's called "Rockin' You," and it's an all new, original and exclusive song by The Jurassic 5! It's short, but no it's not a skit; it's a legit full song with some really tight production, cuts and each MC has a verse. Admittedly, it's all about the radio show, which really limits its outside appeal. It's like those promo songs that groups like The Bizzie Boyz and MC Mitchski would record for Red Alert or Chuck Chillout, and it's as good as those were, except it's for Kevin & Bean. Honestly, it's better than some official Jurassic 5 12"s.
So that's it. If you're the sort of fan who's prepared to pursue Christmas rap to the ends of the Earth, this is a stop you can't miss. Some of the original cassettes are hard to find, but the CDs with the authentic MCs on 'em are all cheap and easy if you want 'em. They're good stocking stuffers for the Hip-Hop head who thinks he has everything, the overlooked odds and ends of Christmas rap.