This next joint is getting lit for a tradition in hip-hop long since passed–not Iceberg sweaters, but album skits. There’ve been so many awful ones that the handful of good ones weren’t enough to keep them from going to hell in a backpack. But a few were incredibly vivid–and funny. Of course, it helped if the rapper performing them sounded cool saying pretty much anything, a la Ghostface Killah (“It feel hot at night…”). Or they were performed by Dave Chappelle, who Talib Kweli brought on board to imitate Nelson Mandela.
As you read on, you’ll realize that three out of the 10 skits collected here are Wu-Tang related. To anyone tempted to complain about that, I say: Fuck off. I’m from the Wally era.
10. “$20 Sack Pyramid”: Dr. Dre, The Chronic (1993)
This was a lot of people’s introduction to the anything-is-possible world of rap skits. Posing as a contestant on a ‘hood version of The 20,000 Pyramid, The D.O.C. does a pretty good job of acting. He had already gotten into the car accident that turned his voice into little more than a strangled whisper, but somehow it worked anyway. Who could forget the digs at Compton’s biggest hater, Tim Dog, with a few shots thrown at Luke for good measure?
9. “Getting Ass, Getting Ass”: Heltah Skeltah, Nocturnal (1996)
Though far from happy-go-lucky, Ruck and Rock always did a good job of straddling the line between hard-as-a-rock and comedic. This skit is pretty funny throughout; Rock initially chastises Ruck for calling a girl (‘What you think you’re a player now, bitch-ass nigga?”) then horns in on the conversation, trying to convince Ruck to “ask her if she got a friend.” The skit culminates with Ruck whipping out his Wanya Morris impersonation and trying to convince his lady to come over with a bit of Boyz II Men’s “Uhh Ahh.” Laughter ensues. SEAN P!
8. “General Hospital”: Kool Keith, Dr. Octagon (1996)
Posing as an alien gynecologist–one of his many personas–Kool Keith attempts unsuccessfully to be a surgeon in this typically weird skit. It’s all to no avail as he utters, “Fuck it, he’s dead” in regards to one of his patients; “There’s a horse in the hospital” just adds to the confusion. Shout out to White Mike from Pitt Street.
7. “Dating Game”: Handsome Boy Modeling School, White People (2004)
Dan the Automator and Prince Paul need a sketch comedy series, as evidenced by this take on The Dating Game with rappers as contestants. Though Tim Meadows gets a few laughs, the real comedic talent is in the dead-on RZA and Jay-Z impersonations. Most credits list Hines Buchanan and Neelam, respectively, as the actors behind those two voices–although some list the RZA as playing himself, which just goes to show how accurate of a portrayal Buchanan did of Bobby Digital.
6. “Pimps (Freestyle at the Fortune 500 Club)”: The Coup, Genocide & Juice (1994)
This was a dope concept but unfortunately, like most stuff The Coup put out, it was slept on. The skit is technically a segue linking two Genocide & Juice compositions to its overlying theme: the real hustlers wear suits and push legislation. The skit starts with some rich people talking money. One guy is asked to do a rapper impersonation. It continues as a part of the following song, serving as hook of sorts.
5. “Fuck Me”: Notorious B.I.G., Ready to Die (1994)
As a freshman in high school I had a dub of the still-new Ready to Die in my Walkman. I played “The What” for this cute junior in my Global I class because it was my favorite song on the album. (Still is.) Of course, the intro came on first. At first, she was humming to Jodeci’s ‘Feenin'”–then she stopped, and her eyes slowly widened. “Oh my God,” she said. My Walkman got passed around for the rest of class, everyone rewinding the skit. Some giggled. Others just stared off, retreating into the recesses of their imaginations, mouths slightly agape while Kim moaned and begged and cursed as Biggie put his thing down in the bedroom. My Walkman fell twice while being passed around, and when I finally got it back after 38 minutes, the right headphone didn’t work. Even worse, as I left, four more fully bearded six-footers wanted to hear the skit, and I was so late for my next class I ended up smoking a blunt in the staircase with the aforementioned hooligans.
4. “Packinamac Part 1 and 2”: Big Pun, Capitol Punishment (1998)
Just when you thought that Big Pun was going to be kicking some watered-down Raekwon skit, him and his sidekick Cuban Link turned the entire drama of a shoot out into a hilarious sketch with both rappers singing “PackintheMacintheBackkoftheAc” at fast as they can until it’s little more than fast gibberish. Silly, yes, but refreshing when you consider that most rappers take themselves too seriously to ever just act silly. Miss you, Pun. You were the illest, but also a funny, gregarious dude.
3. “Rude Boy”: Cam’ron, Purple Haze (2004)
When I worked at a hip-hop publication, two of my coworkers used to argue for hours whether this skit was real or not. They both stated good cases. The phone conversation between Cam’ron and the jealous Jamaican boyfriend of a girl Cam is having relations with does seem quite real at times. The best line is when the dread on the proclaims that the “word around town is that ya mingle wit my ting star,” and “The massive no play games.” Cam didn’t have to do much more than chuckle and antagonize the cuckold to make the skit classic.
2. “Killer Tape”: Wu-Tang Clan, Enter the Wu-Tang (36 Chambers) (1993)
What is there to say about “Killer Tape” that hasn’t been said? There’s a missing John Woo VHS being sought when breaking hood news comes banging on the door in the form of Ghostface Killah. This dialogue changed the way people spoke. Can you in all honesty say you knew what they were talking about the first time you heard it? “Niggas came through in the Land?” “I’m going to get my culture cipher?” RZA was right: People really weren’t figuring it out until the year 2G. (By the way, culture cipher means 40 as in 40 oz. Peace to the Gods.)
1. “Woodrow the Basehead”: Ghostface, Supreme Clientele (2000)
Superb bodied this one as Woodrow, the dollar-short basehead. He could’ve been casted on The Wire and outdone Bubbles without even trying. Funny though it may seem, it’s still serious subject matter, and the initial friendliness is just a façade. Ghost is hustlin’ crack but Woodrow, being a dollar short for two crack rocks, tries to hustle a crack dealer. It gets deep when you think about it. Drug addiction, economics, morals, degradation… and it all centers on a single solitary dollar bill, dollar bill. As Superb so eloquently put it, “One muthafucking dollar?” Superb, where the fuck you at? You should be acting.
• The little kids on OutKast’s Aquemini skit for “Art of Storytelling 1 and 2”
• Everything Ghost said on Only Built 4 Cuban Linx.
(Shout out to Knuckles/Clyde Smith who couldn’t be on the list because he violated parole.)