Glenn Collins’s infamous 1988 New York Times article, which trumpeted at least a few years too late the entry of hip-hop into America’s musical mainstream, begins with a sentence so corny in its attempt to adopt the emergent street slang of the time that it’s hard to read without your eyes tearing up. The article, entitled “Rap Music: Brash and Swaggering, Enters The Mainstream,” leads with the statement “Rap is so stupid def, it’s bum-rushin’ the mainstream. It’s housin’ ‘em all - word, homes. Translation: Rap is so incredibly fine, it’s breaking down the doors of mainstream society. It’s bringing down the house - and that’s the truth, friend.”

It’s fitting that this article leads with such a horrendously dorky paragraph. Because though rap music, perhaps in a less brash and swaggering iteration, had entered the mainstream ten years earlier, by the late ’80s, the advertising world was figuring out ways to really market the living shit out of urban culture, and doing so with very little attention paid to the genre’s purported street cred.

So on the one hand you have the now widely-accepted insight, that some of the more socially conscious and expressive rap of that era got overlooked by a mainstream marketing blitz specifically designed to sell a hardass urban lifestyle to the lilywhite youth of the suburbs. On the other, and much funnier hand, you have those hopelessly sanitized, painfully awkward attempts to squeeze the sound of an emerging youth culture into one that was kid-friendly, family-friendly, advertiser-friendly; friendlier than the friendliest song on the friendliest album by the friendliest artist of the era (probably DJ Jazzy Jeff and the Fresh Prince’s He’s the DJ, I’m The Rapper) could ever hope to be.

You can argue about what exactly it was that they weren’t getting, but marketers, like Collins, heard rap music, and didn’t quite get it. And so, hip-hop’s conventions were used to hawk basically everything, in ways that make Debbie Harry’s groundbreaking albeit stilted attempts at flowing in Blondie’s “Rapture” sound like the work of an experienced MC. Here are just a few examples of hip-hop as a marketing tool gone horribly, dorkily awry; from somewhere around the point at which The New York Times realized that it existed.

5. Fruity Pebbles “Barney The Master Rapper” / “CD Rapper” - c. 1991

Fred Flintstone and Barney Rubble have never been strangers to selling shit. Their neo-vaudevillian antics had been used to market cigarettes to children at least into the early-’60s. But by 1971, they were no longer able to legally expound upon the full, smooth flavor of Winstons, and so their visages were put in the service of selling the most deliciously addictive breakfast cereal around. In the early ’90s, a few of the duo’s most memorable spots as the spokes-characters for Fruity Pebbles brought a faux-urban sensibility to their pre-Cambrian world. In one, Barney arrives in the guise of The Master Rapper, decked out in chains, big sneakers, and lugging what was referred to in the suburbs (with little attention paid to the socio-economic connotations) as a “ghetto blaster,” dropping anachronistic, cereal-centric rhymes like so much poop from an anthropomorphic mastodon. In another ad from the era, Barney is introduced as “CD Rapper,” an MC Hammer knock-off who bamboozles Fred with his repertoire of sick dance moves. These commercials, though dated and goofy, are hardly the most cringe-worthy, if not just because breakfast cereal doesn’t really have to be “hip” to sell.

4. The Superbowl Shuffle - 1985

1985 was a solid three years before rap, according to The New York Times, entered America’s mainstream. That year, you really had to dig to find traces of the nascent genre. Chances are you wouldn’t hear hip-hop unless you were hanging out with original B-boys in The Bronx, or if you happened to turn on your television to watch the biggest fucking sporting event in the entire country.

“The Superbowl Shuffle” was a ditty so infectious and ubiquitous that it united the nerdiest child with those jocks who would, years later, kick his ass. Performed by the “Chicago Bears Shufflin’ Crew,” which doubled as the 1985 lineup of the Chicago Bears, the song and titular dance that accompanied it didn’t ask much. Granted, throughout the promo spot, the more intrepid members of The Crew are seen busting moves with varying degrees of skill. But this wasn’t the Superbowl Hustle, or even the Superbowl Roger Rabbit, it was merely a shuffle, and required only the ability to unsurely step once to the left, then once to the right, then repeating. The mitigating factor, with regard to the song’s painfulness, is that some of the players actually exhibit some signs of being able to flow. Most of The Crew, however, dart and jitter their way through their lines, shred on unplugged, soundless electric guitars like ADD 8-year-olds, and give the general impression that they’re not certain exactly how they ended up getting roped into doing a song and dance routine. Oh, and there’s one guy whose job it is to wail on the bongos. The highlight of the performance is Jim McMahon, whose green-screened, Joe Cool visage pops up throughout the video. Watched in the fullness of time, this reminds us of a simpler day, when one’s bad-ass outlaw status was determined merely by if one was wearing sunglasses or not.

3. Don’t Let The Wrapper Fool You – c. 1991

It’s kind of comforting that in a day in which we’re constantly bombarded with nostalgia-porn, it’s still possible to have a pop-culture memory that hasn’t been indexed by Google. “Don’t Let The Wrapper Fool You” is one of those increasingly rare nuggets of late-’80s pop detritus for which all searches come up mostly blank.

What we’re left with is a chorus imbedded in our collective minds that can’t be lobotomized out. “Rap rap rap (or wrap rap wrap, or some combination of those homonyms) don’t let the wrapper fool you.” This song made its appearance on some Earth Day-related video shown to middle-schoolers nationwide.

Earth Day, if you’ve forgotten, was a holiday that was celebrated once in the ’70s and once in the ’90s. In these two brief moments, sustainable living was in, plastic forks in the cafeteria were out, and the EPA was still acting in good faith rather than shilling for big business.

In 1991, year of the second and final Earth Day celebration, we students were going to plaster that hole in the ozone layer right up with our paper mache’ and recycled soda bottle artwork, and fuck if we were using any chlorofluorocarbons in the process. “Don’t Let The Wrapper Fool You” was to be our marching song, tantamount to an early echo-boomer take on The Who’s “Won’t Get Fooled Again”, only better, because it told us exactly what we weren’t going to be fooled by.

And though a year or two later everyone returned to not giving a shit about anything, this crappy song remained lodged somewhere in our minds. Most notable is the fact that within the chorus, the song states the name of the genre of music to which it purportedly belongs. This may very well be a mistaken attempt on the part of the songwriter to hearken back to the days in which Rock and Roll songs still talked about rocking and rolling, but from this vantage point it looks like a horrifying precursor to a trend that would emerge among third-wave ska bands a few years later.

2. Teen Witch – “Top That” – 1989

An argument can probably be made that whimsical monster movies for adolescents have disappeared because life for teens has become monstrous enough on its own. Facing down a collapsing economy and conclusive scientific proof that pretty much everything you can possibly do causes cancer, it’s hard to imagine some teenager get tickled at the notion of a werewolf slam-dunking a basketball. But in the late-’80s, everything was different. You just sat down on the couch, flipped on The Monster Squad, and ate tub after tub of margarine, biding your time. Then you went to college, the four year romp that would guarantee you any job you wanted. This is the culture that gave us Teen Witch.

The musical number in question, which is now living out a second life as a top-tier internet meme, begins with two girls riding bikes. They come upon the archetypical popular guy and his two buddies. As popular people are wont to do, the trio are hanging out in front of a hot-rod and doing a choreographed dance to the tune of some homemade casio beats. The girls watch the guys dance, and do these fellows ever dance. They dance in a way that seems to leave all the body parts that should be moving standing still, while all the part that should remain static jerk back-and-forth furiously, arrhythmically, wildly. And as the alpha-popular guy dances, he raps, in a thin, nasal tone and a command rhythm about on par with the dancing.

“I will never be hip,” mourns the on-looking female sidekick. Her friend, supernaturally gifted, grants her the power to break shit down. She rolls up to the dancers, seamlessly works her way into their routine, and unloads dis after slammin’ dis at the wifebeater-clad meathead, inviting him at the song’s end to “top that,” leaving him flabbergasted. Hardly the only goofy musical number in Teen Witch, this unfortunate flirtation with hip-hop cements it as the most remarkably painful. The fact that it remains embarrassing to watch to this very second will no doubt keep it circulating around the “Can You Believe This Shit?” portion of the blogosphere for some time to come.

1. Vanilla Ice – “Ninja Rap” – 1991

1991 was a significant year for culture and a shitty year for Vanilla Ice. These two truisms were less coincidental than people tend to think. We have our handed-down cultural myths about how, in the mid-’90s, “grunge killed hair metal” and shit got real. The reality of the situation is infinitely more complex. Far more germane to the current way we understand and experience pop culture than the release of Nirvana’s Nevermind is the earlier, very specific day when Vanilla Ice stopped being cool.

Many a middle-schooler riding the bus found himself made fun of that day, for being hopelessly behind the curve on what to dislike. Only hours earlier, every early-teenager in the United States was clamoring to shave lines into his eyebrows and dye lines in his pompadour. Now, they approached Vanilla and his music with an arsenal of creative profanity really only available to people around the age of 13. This marked the beginning of something big.

Sure, Vanilla Ice’s “Ninja Rap” remains, by far one of the most embarrassing misuses of urban pop culture in a mainstream setting (and that’s saying a lot, given that the song came from an artist whose very name remains synonymous with the idea of cashing in on a mollified version of someone else’s shtick.) It was a musical sequence in a movie (Teenage Mutant Ninja Turtles II: The Secret of the Ooze) involving a pop-star dancing around with four Chuck-e-Cheese reject bipedal turtle puppets, ones who knew ninjitsu and talked like surfers. It was a song of which the sole lyrical focus was these turtles and their practice of ninjitsu. It was not written for longevity. It was a song with the chorus, “Go Ninja, Go Ninja, Go.” Who the fuck vetted this thing? It’s as if no one foresaw that poor Ice was going to catch heat for making light of what was supposedly the sound of the streets about ten seconds after that came out.

But on the other hand, didn’t Prince have a hit on his hands just a few years earlier with “Batdance”? In that light, “Ninja Rap” wasn’t just a terrible idea, it was a turning point. No longer was there a slow burn towards obscurity for one-hit wonders whose time in the limelight was over. Every mega-celebrity from there on out who got stale seemed to endure extreme public humiliation within seconds of passing the sell-by date. Poor MC Hammer, after making the same mistake with the “Addams Family Groove” that same year, suffered a similar fall. However, even his attempted 1994 comeback, which involved the man wearing a Speedo into which were stuffed a massive banana and two mandarin oranges in the video for “Pumps and a Bump”, didn’t incur quite the resounding wrath that Vanilla Ice’s did.

And so, “Ninja Rap” is not just the one of the more embarrassing attempts in musical history at using hip-hop to push a line of action figures. It’s one that tells us the most about ourselves. We learned, the day that “Ninja Rap” hit the radio, to immediately turn on the things that we once held dear. Pop culture trends were finally completely subject to planned obsolescence. Poor Vanilla Ice, meanwhile, a mere pawn in maneuverings of the mainstream culture industry, ended up not only enduring the first “Five Minutes Hate” of a generation, but (if the legend is true) getting hung out of a window by his ankles for his trouble. “Go Ninja, Go,” indeed.

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