The classic rap-album skit. It’s impossible to imagine Doggystyle without those hazy, ’70s-referencing interludes scattered throughout the album. Remember early JAY-Z’s fixation with gangster-film nods? For a long time, skits were as much a part of album-making as the songs themselves.

As albums have shifted from cassette to disc to mp3 to streaming, the way that we engage with those albums has also shifted. Listeners today are much more likely to corral their favorite tracks into playlists than sit through an entire album every time they want to put on their favorite artists. As a result, the thematic qualities of album-making have become less centered on how we appraise said albums and the artists who create them. 

In earlier eras, conceptualizing an album was a trick that was almost imperative if you were making music for people to listen to on a tape or CD. And in Hip-Hop, that often meant tying projects together with intros, interludes, and outros — a convenient way to notate just how the album was intended to be consumed and give it all a sense of continuity and unity.

Skits mattered. Until they didn’t. 

There was always an art to the perfect rap-album skit. It was part placement, part connectivity, and all about how creative a skit could get without making the listener want to skip to the next track. Hip-Hop skits became a semi-cornerstone of the great Hip-Hop album; you’d be hard-pressed to name a classic rap album after 1988 that didn’t open with some kind of intro or feature some obligatory interlude. They could become extraneous, but at their best, skits helped fuel a sense of conceptualism on some of Hip-Hop’s best long players.

And among those classic skits, these were the most memorable.

Dr. Dre, “The $20 Sack Pyramid” (The Chronic, 1992)

The D.O.C., Snoop Doggy Dogg, and “Big Tittie Nicki” star in this Compton-friendly spoof of the $100,000 Pyramid, as two stoners named Duck Mouth and Bootney Lee Farnsworth compete for a dub of weed. There’s also a $35 coupon for the Compton Swap Meet to sweeten the deal, and references to everybody from En Vogue to Tim Dog. Proof positive that even the Gz had a sense of humor.

De La Soul, “Intro” (3 Feet High and Rising, 1989)

The original (and still the best) Hip-Hop game-show spoof is this quirky classic from De La Soul and Prince Paul. With Posdnuos, Dave, and Mase as contestants, album engineer Al Watts serves as host of the strangest trivia game show of all time. De La’s voices are goofily terrible (and producer Prince Paul shows up as a nervous fourth contestant), and it only adds to the nonsensical, juvenile humor. Watts grills the trio with a classic barrage that Hip-Hop fans still can’t answer: “How many feathers are on a Perdue chicken? How many fibers are intertwined in a Shredded Wheat biscuit? What does ‘Tuhs eht lleh pu’ mean? How many times did the Batmobile catch a flat?”

LL COOL J, “On the Ill Tip”(Bigger and Deffer, 1987)

“We did it again!” Its brevity notwithstanding, LL’s album closer for his sophomore banger is one of Hip-Hop’s first “Fuck the haters” salvos in a career that would become defined by them. LL and his crew laugh hysterically as L boasts about recording his sophomore project, in spite of all who doubted him.

On the heels of his debut Radio’s platinum success, Bigger and Deffer would make LL COOL J a bigger crossover star on the strength of popular music videos for “I Need Love” and “I’m Bad.” And LL was clearly feeling himself even before the album went on to sell 2 million copies in the U.S. and shot to No. 1 on the Rap Charts in 1987. “Another album!” he declares over congratulatory chuckles from his boys. “The joke’s on you, Jack!” It shows how a healthy chip on his shoulder has always served James Todd Smith well.

OutKast, “Kim & Cookie (Interlude)” (Stankonia, 2000)

The kind of phone conversation that no man wants to believe has ever been had about him, this classic interlude from the legendary ATLiens features two homegirls going in on one’s less-than-impressive one night stand. His endowment (or lack thereof), inability to last more than a short while, and just how close he came to getting robbed are all fodder for hysterics in the exchange. Kim and Cookie sound like they could be any two friends talking on a Friday night — and the skit serves as a perfect setup for the following double-entendre classic, “I’ll Call Before I Come.”

Ghostface Killah, “Woodrow the Base Head” (Supreme Clientele, 2000)

“Cash rules everything around you — well crack rules everything around me!” Woodrow is a character that so many neighborhoods know all too well. The local addict on the corner is centered in this classic bit from Ghostface Killah’s seminal second album, and it’s one of the funniest skits of the classic rap era. From Woodrow’s request (“Give me two cracks”) to his confrontation with Ghost’s bodyguard, it’s clear that the rap superstar has love for the neighborhood fiend.

Things start off friendly enough, but Woodrow’s haggling eventually gets to Ghost, though he remains friendly. (“You like family — I love you, man.”) Even as ’Drow only offers $9 and promises to come through with VCRs, Ghost just wants ’Drow to move on before things get tense. “You think I don’t carry a pistol because I’m a crackhead?” ’Drow warns, before acknowledging that he’s gonna have to go see “the rastas.”

“They let me get it for $7…” 

UGK, “Intro” (Ridin’ Dirty, 1996)

Some skits serve as humorous distractions on classic albums, and some make for soberingly real backdrops for the music that surrounds them. The latter is the case with UGK’s 1996 classic Ridin’ Dirty. Smoke D’s hazy commentary on prison life comes from real phone calls recorded during his stay at a Mississippi state penitentiary, and they add to the album’s thematic realness. “I get treated like the motherfuckin’ pope in here, nigga,” he declares on the album opener, and it sets the stage for Bun B and Pimp C’s laid-back Texas storytelling.

Mase, “Watch Your Back” (Harlem World, 1997)

Bad Boy skits became showcases for the label’s cocky-and-flossy image at its peak, and a young Mason Betha reveled in his playboy status on this hilarious bit from his hit debut album. Between clenched-teeth compliments (“I’m a fan of yours, you know, my kids like you, they dance to you…”) and teetering-on-the-brink whininess, a caller threatens the Harlem rapper. “You wild easy to get, son!”

Mase’s short, bemused reactions are pricelessly cavalier, and the convo is a brief but funny moment on an album with no shortage of memorable bits.

The Notorious B.I.G., “The Mad Rapper/Kick in the Door” (Life After Death, 1997)

Though not a standalone track unto itself, the classic Madd Rapper bit would become one of the iconic skits in Hip-Hop history. Containing not-so-thinly-veiled shots at 2Pac and Wu, the bit features an angry Hip-Hop artist (played by Deric “D-Dot” Angelettie) railing against Biggie and Bad Boy’s success on what sounds like a daytime talk show, hosted by “Trevin Jones” for Bad Boy Television.

“This my fourth album, yo! My fourth album!” D-Dot later explained the skit was spontaneous, and he recruited employees around the studio to record it. “It was all made up right then and there,” he told Genius. “Nothing was planned out.”

Redman, “Chicken Head Convention”(Muddy Waters, 1996)

Redman’s obnoxiously funny bit features a background of clucking chickens, references to boosted clothes, and baby mama clichés. The premise is pretty clear: hoodrats galore, all in attendance at a convention for the kind of girls with the “big weaves” and “bad attitudes,” who might have pictures pasted on the glass over your corner convenience store counter. Nikki D guests as the interviewer, asking probing questions of the chicken heads in attendance.

Redman’s unapologetically incorrigible persona was never more engaging than in the late 1990s, just before he’d go full Cheech & Chong with Method Man and after he’d started to become more of a household name outside of East Coast rap circles. “Chicken Head Convention” showcases his juvenile sense of humor at its best (or worst?) and still elicits uncomfortable chuckles almost 25 years later.

Eminem, “Steve Berman” (The Marshall Mathers LP, 2000)

Eminem has more than a few memorable skits across his legendary career, but the famous harangue from Interscope’s then-President of Sales and Marketing ranks at the top. Serving as a go-between for Em and Interscope Records couldn’t have been easy, and you feel for Steve Berman in this classic skit from Em’s 2000 masterpiece. A brilliant bit highlighting Em’s struggles with label pressure, the conversation is Berman’s chance to berate his superstar artist, to uproarious effect.

Berman slams the controversial rapper for the album he’s turned in. “Tower Records told me to shove this record up my ass!” exclaims an exasperated Berman. “Do you know what it feels like to be told to have a record shoved up your ass?”

Kanye West, “Wake Up, Mr. West” (Late Registration, 2005)

DeRay Davis’s impression of the late, great Bernie Mac is as affectionate as it is dead-on, and it opens Yeezy’s acclaimed sophomore album in memorable fashion. Following up his bit on The College Dropout, DeRay-as-Bernie admonishes West for sleeping in his class and dressing like a “goddamn fourth grader.”

Kanye wanted Bernie himself for the bits on The College Dropout but recruited Davis after hearing him goofing on Mac’s voice in the studio. Davis would deliver on the other memorable moments throughout Registration, as the voice of the recurring “Broke Phi Broke” theme in the skits all over the project.

* Banner Image: CREDIT: De La Soul / Photo by Michael Ochs Archives/Getty Images