It’s Weird ’90s Week on Stereogum. All week long we’re looking at the strangest musical moments and trends of the decade. Check out more here.

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If ’90s rap were a school cafeteria at lunchtime, fans would be thoroughly perplexed about which table to set their tray on. You have the Afrocentric jazz cats at one table, probably eating biltong, fufu, injera, or something of the like, with black string African medallions around their necks discussing the most obscure jazz on the planet. You’ve got grimy, gully East Coast juvenile delinquents recounting violent crime-filled anecdotes over school-provided lunches at another table. The West Coast gangsters doing the same thing as their East Coast counterparts except with drive-bys in their stories, donning occasional red and blue fits. The conscious/revolutionary table salty at the cafeteria for only serving non-healthy options and disappointed in the other tables for scarfing them down willingly, rhyming about it while hammering out beats on the table. The Dirty South table is plotting domination over grits and biscuits. But the only group met with unified disdain by everyone else in the room is the awkward, goofy, dancing rappers posting flyers for the school talent show, more concerned with getting all the attention possible than socializing or sustenance. Still, for a short, peculiar time, they ate all the empty calories they were offered.

Rap was born in the late 1970s in New York City, which might help to explain why it had so many competing parts to its identity by the ’90s. It was going through some growing pains. It was like a teenage boy with braces, hand-me-down clothes, and feet far too big for its current height. Early ’90s rap was still grappling with the MC rising to prominence over b-boys, graffiti writers, DJs, and beatboxers. And though it was clear the MC would be the most effective purveyor of the culture, it wasn’t clear what type of MC would prevail and propagate it furthest. Purists and stalwarts were fiercely protective of this burgeoning form of black expression, and there wasn’t about to be no half-steppers leading the way — not if they had anything to say about it.

The blueprint and catalyst for family-friendly, conveniently packaged rap was DJ Jazzy Jeff And The Fresh Prince; that duo’s music was in direct opposition to the revolutionary spurrings of Public Enemy and N.W.A, and it rubbed the other factions in the middle of the consciousness spectrum the wrong way, as well.

This conflict led to an interesting dynamic among ’90s hip-hop sects, with many moving parts that would only align against those who were seen as the most shameful exploiters and commodifiers of the culture. But lining up on the other side were millions of fans who bought into the dances, the parachute pants, the fabricated pasts, the fits rocked backwards, the sky-high flattops, the songs about mutated turtles named after Renaissance painters, and the lesser rhyme skills. It was a time when Q-Tip of A Tribe Called Quest would call out one MC Hammer on “Check The Rhime” with the line: “Proper. What you say, Hammer? ‘Proper’? / Rap is not pop; if you call it that, then stop.” But it was also a time when the minds that sculpted the Ice that is Vanilla scribbled in a notepad and created a life, and it didn’t matter for a while because he could admittedly dance his ass off, keeping people dizzied long enough to believe his manufactured hood upbringing and buy 15 million copies of his debut.

V-Ice and Hammer were not alone, though. For a brief moment in the ’90s, absurdity sold, and some weird shit went down as a result. There’s really no one in rap today who can or wants to claim the “traditions” from this peculiar period in hip-hop, and though there are similarities to what’s ruling the radio today, there will never be anything quite like what transpired in hip-hop during the early ’90s. Here’s a look at the first wave hip-pop artists from least to most weird.

Heavy D

First of all, RIP. Second of all, Heavy D was pretty legit. Dude could spit and he had the credentials to get DJ Premier and Pete Rock to produce cuts for him. But Hev could also move for a hefty fella at 6’4″ and well over 300 pounds in his prime. There would have been no room for the overweight lover had V-Ice and Hammer not cleared the path for him, and he would have never racked up three platinum and two gold albums without those dance moves. Heavy Hev was an odd mix of hip-hop, R&B, a little of bit of reggae from his Jamaican roots, and agile dance moves in shiny vinyl sweatsuits, and though he was the least weird of the pop-hoppers, he provides a good jumping-off point.

Kriss Kross

Another RIP is in order here for one half of this duo, Chris “Mac Daddy” Kelly. But Kris Kross were pretty much a huge, lucrative gimmick. Jermaine Dupri struck platinum and gold when he discovered two kids in an Atlanta Mall who could deliver rhymes well. The duo was talented, but the whole backwards baggy-clothes schtick along with heavily choreographed dance videos and being only 13 years old helped propel them to two platinum albums and a supporting spot on Michael Jackson’s European Dangerous tour. The VHS tapes of the music video for Totally Krossed Out’s “Jump” sold more than 100,000 copies alone. They may not have been the wiggity, wiggity, wiggity wackest, but they were a weird phenomenon for a while.

Kid ‘N Play

To sum up Kid ‘N Play: They made more movies than albums together. They turned in two gold efforts with 1988’s 2 Hype and 1990’s Funhouse, but they were more known for their three House Party films made between 1990 and 1994. The biggest takeaway from those movies, and what still persists today, is their signature dance known as the Funky Charleston or the Kid ‘N Play kick step. They were safe, fun rap with overwhelmingly positive lyrics and lots of party and dance directives. House Party was originally meant for DJ Jazzy Jeff And The Fresh Prince, but there were plenty of watered-down, family-approved acts in this weird ’90s period, so Kid ‘N Play blew up off the films instead.

Digital Underground (“The Humpty Dance”)

Digital Underground were actually pretty dope. This collective could rhyme, and they gave Tupac Shakur his start. But 1990’s “The Humpty Dance” was a weird hit for the crew. Digital Underground member Shock G used his alter ego Humpty Hump to “ruin the image and the style that you’re used to.” It was meant as a jab at MC Hammer and Vanilla Ice, the most successful rappers at the time, and the crude dance “The Hump” was meant to be a direct contrast to the precise, strictly choreographed movements of V-Ice and Hammer. The lyrics were raunchy, mostly detailing Humpty’s sexual prowess with lines like “I once got busy in a Burger King bathroom.” It was a refutation of the corny lyrics that Hammer spit. But many people missed the point, and it was in turn taken seriously as a dance. The song hit #1 on the rap singles charts, and it was the most successful single on Digital Underground’s Sex Packets LP, despite being an outlier on the album. It was a case of satire taken literally, but in retrospect, it was genius for Shock G to don a huge fake nose, fur cap, and tacky suit to comment on the most popular artists of the moment.

Sir Mix-A-Lot

“Baby Got Back” gets the party cracking to this day, and thanks to an update from Nicki Minaj’s “Anaconda,” it’s enjoying a relevance not afforded to others on this list, but it sure was a fascinating blip. The big booty anthem was a part of the movement to make voluptuous butts happen in mainstream culture, and it may have been the origins of Beyonce’s “Becky with the good hair,” but it was certainly the sole reason why 1992’s Mack Daddy went platinum. Had it not been for the dance/rap hybrids that welcomed heavy background dancing, and the absurdity of acts like MC Hammer and Kris Kross, this song would never have taken off the way it did. Sir Mix-A-Lot’s deeper album cuts had some discussions of the realities of a Seattle that no one really knew or cared about, and that shouldn’t be overlooked, but he owes his fame and attention to artists that paved the way for his ass-tronomical ode, because that was a lot of space to clear.

Fu-Schnickens

What kind of name is Fu-Schnickens? Seriously? You can’t say they weren’t committed though, each member added the Fu to their moniker like the Ramones. Honestly, they could spit, with blistering cadences, dexterous flows, and even backwards raps, and they had production from A Tribe Called Quest all over their first album. Phife Dawg (RIP) was even featured on F.U. Don’t Take It Personal’s second single, “La Schmoove.” Rapping with lightning quickness and backwards phonetics can either come off corny or dope, and there is a fine line. Initially it seemed the reception of their debut appeared to veer toward the dope side, but after featuring Shaquille O’Neal on the lead single from their second album, Nervous Breakdown, their aesthetic just seemed gimmicky. De La Soul and A Tribe Called Quest were already holding it down on the trio front, and there were enough shenanigan acts at the time that Schnicks could easily slip into obscurity after their second album as people came to recognize them as the diluted ATCQ that they were.

Marky Mark And The Funky Bunch

Mark Wahlberg’s brief rap career was pretty peculiar. He gained entry to the music world through his brother Donnie’s success in New Kids On The Block, but he wasn’t even close to boy band material. By age 13, he had developed a cocaine addiction. At 15, he had a civil action filed against him for two separate instances of shouting racial slurs and violence against black children. At 16 he committed a string of hate crimes and was finally charged with attempted murder and assault, and was sentenced to two years in Suffolk County Deer Island House Of Correction, ultimately serving 45 days of his sentence. So there was no need to fabricate a hard past like Vanilla Ice, but after being released from prison he hooked up with the Funky Bunch and made some of the softest, most commercial rap ever. He even modeled in a Calvin Klein ad after the world saw his physique on MTV in the “Good Vibrations” video. He could have rapped about some real shit, coming to terms with his racial issues and trying to actually rehabilitate himself after jail, but he rode the first wave of hip-pop hard instead. His debut, Music For The People, went platinum despite his past. If the fact that a criminal, bigot, and brother to a pop sensation could succeed in early ’90s doesn’t convince you that it was a weird time for rap, I don’t know what will.

Vanilla Ice

It’s no wonder why people were ready to believe the rumor that Suge Knight dangled Vanilla Ice from a balcony to get him to sign over his publishing rights. Ice was easy to hate. This man created a false hood past for himself in a genre that was all bout authenticity. That is unforgivable. But before people realized that his story was completely fabricated, he sold more than 15 million copies of his studio debut To The Extreme. His resurgence as a reality star and TV host is probably weirder but that’s a discussion for another decade.

MC Hammer

No sympathy for MC Hammer here. If he didn’t have the nerve to begin his most famous video, “U Can’t Touch This,” with footage of him robbing better artists of several awards, things might be different. But MC Hammer is the most reviled ’90s pop-hop star for a reason. Partly, rightly, due to those stupid-ass parachute pants and genie outfits that were more suitable for Disney’s Aladdin on Ice than anything else. But mostly because the dude also had zero humility about his “success.” He bought a huge mansion on a hill, and from there, he looked down at everyone, though they were the same people lifting the culture his riches and accolades were built upon. All that aside, the fact that he could throw on some parachute pants, spit some mediocre rhymes, and ignore being raised in one of the most impoverished cities of America (Oakland) to dance his way to plaques is truly a testament to how weird things got for rap as it was getting comfortable in its skin in the early ’90s.

MC Skat Kat

On the real, this may have been the weirdest stunt to go down in not just rap, but all music, ever. MC Skat Kat was an animated cat that got his start rhyming on the cold streets of Paula Abdul’s “Opposites Attract” video in 1989. Taylor Steele, the voice behind the whiskers, got the idea for Skat Kat watching the Gene Kelly movie Anchors Aweigh in which Kelly’s character dances with Jerry, the mouse from the Tom And Jerry cartoon. So Steele thought he would flip the script and have Abdul dance with a cat. Romany Malco (40 Year Old Virgin, Think Like a Man) wrote Skat Kat’s verse on “Opposites Attract,” and then things got weird. First, Steele began sessions and rehearsals in a full cat costume, and eventually the character would be animated courtesy of members of Disney and Warner Brothers’ animation team. Some clown thought it would be a good idea to have the cat “record” an album, and thus The Adventures Of MC Skat Kat And The Stray Mob was released in 1991. Not surprisingly, the video was one of the most requested on MTV, but it only reached a dismal #96 on the Billboard Hot 100. Hell, I don’t blame the people behind this though. If Vanilla Ice can fabricate a hard-knock past as a human being, why can’t a fictional animated cat have his day?