Five Rap Songs We Love That We're Probably Not Even Supposed To Like

We don’t believe in guilty pleasures.

At least not in any musical form.

If you’re enjoying yourself, and not hurting anybody in the process, do you.

But we must admit, that it took us awhile to reach this new era of enlightenment, not to be confused with being too old to care what anyone else thinks.

Or maybe that’s exactly what it is.

Either way, in this special double-shot of The Five Spot, we’re taking a trip down memory lane, while also cleaning out our closet, and clearing our conscience.

This is Part Two of two, the rap incarnation, aka “Five Rap Songs We Love That We’re Probably Not Supposed to Even Like”.

If you missed the prior rock installment of this same deliciously dubious category, you can check it out by clicking here.

Now on with the show...

“Gucci Gucci”-Kreayshawn

This was the song that originally inspired this double-shot of The Five Spot. Oakland-bred Kreayshawn blew up off this cut, which led to a major-label bidding war, and landed her on the esteemed Columbia Records label. The problem was, by the time her debut album dropped, this song’s shelf-life had already peaked, so her momentum had all but stopped. While the backlash, plus lack of a follow-up hit anywhere near this level, combined to kill her career off like a hotshot.

After showing this video to my West Coast homie (future Wudder podcast contributor) Big Rob, he stated “boy, you need your ass kicked for liking this song”. Exactly my point. The group of rap fans, three decades into consuming this culture, who would list this as a Top 10 Female Rap Single of All-Time, likely consists of just me, myself and I. I’m okay with that. This song is unabashedly bratty greatness. Extremely hilarious, but with an encoded message and serious bass thump. If people wanna claim Macklemore’s “Thrift Shop” as a more respectable testament to forgoing designer-labels, while finding your own sense of style and fashion? Then your boy Bomb is calling you a chump.

Shout-out also to the brilliantly named Lil’ Debbie, Kreay’s road dawg in the now-defunct White Girl Mob, for whom this video represented a coming-out party.

“40 Bars”-Jewelz aka The Answer aka Allen Iverson

Make no mistake, The Wudder’s love for Allen Iverson borders on irrational at times. Perhaps this song being on the list is proof positive of this fact. But whatever, we’re self-aware enough to own that, while also telling y’all we just don’t care. This song, and AI’s debut album as Jewelz on Universal Records, due to then-NBA commissioner David Sterns behind-the-scenes machinations, never saw the light of day as a formal release.

Most of the album has never been heard, outside of a few boardrooms, or by the approximately 5000 members of AI’s entourage at the dawn of the 2000's. This song, however, got some local radio play before the intervention, possibly even for reasons beyond Iverson’s athletic talent and hip-hop generation icon status. Still, the league’s corporate interests, who would go on to institute a dress-code + put a zone in the league just to stop him, were not ready to have The Notorious MVP out here rapping like the third-member of Mobb Deep over a Havoc knockoff beat. And for non-gangsta-rap fan listening to these lyrics, which AI delivers here in bracingly authentic fashion, albeit in his own off-beat flow, you almost can’t blame them.

“Jam On It”-Newcleus

I expect some objections to this one. Not because they don’t like the song, because most people, even casual fans of rap music, know that “Jam On It” is a jam. Some people might protest it being on the list, because they’d say it’s already acknowledged as such. My words to them would simply be: not enough. This does not get put in any of the big lists of seminal, influential rap hits of the late-70’s/early-80’s pre-album-rap-era like “Rappers Delight”, “The Message”, “Planet Rock”, “The Breaks” or “The Show” does.

And for me, it’s in that company. This might actually be the first song to spark the flame inside me at age 8. It was either this, while watching people breakdance at an elementary school talent show, or hearing “The Show” with my older cousin Shane out front of my grandmother’s house, in the back of my Uncle Paul’s Gran Torino. The “I’m Cosmo Dee from Outer Space” line, hit me the same way “Six Minutes, Doug E Fresh, You’re On” did. In both cases back in ‘84/85, this was music that really did feel like it had come from outer space. It was coming from only an hour or so away in New York City, but I didn’t realize that at the time. All I knew, is that these Space Invaders landed inside my mind. Shortly thereafter, I was fully entrenched, in a lifelong love affair with beats and rhymes.

You won’t see “Jam On It” in any of these newfangled interlopers old-school round-up countdowns. “Jam On It”, a song with a chanted break of “Wiki Wiki Wiki Wiki”, doesn’t even have its own damn Wikipedia page. So, we’re putting this on the list, for millennial rap fans, a few years younger than me, who may have never even heard of Newcleus.

RIP Chilly B. Jam On…

“I’m The Type Of Guy”-LL Cool J

LL Cool J is a legend of the highest hip-hop order. But the Summer of 1989 was the first time that a large contingent of hip-hop culture turned on him. They did so for a few reasons, some of his own doing, along with the sweltering cultural climate in the 1989-a-number-another-summer of PE & African medallions, along with internal jealousies in a genre that had few stars of LL’s stature at the time. “I’m The Type of Guy”, the lead single off the critically panned Walking with a Panther, was emblematic of all that.

It is a dirty-macking anthem, delivered in a ladies-man voice, taunting every dude whose girl he’s taking.  LL was so cocky by this stage, that he actually bragged about his ability to fellate himself on another song from this album. He was even famously booed that summer at a Harlem “Stop The Racism” rally for Yusef Hawkins, a 16-year-old black teenager killed by a white mob in a racially motivated attack in Bensonhurst, Brooklyn.

At 13, I was too young to fully understand all the LL-as-lightning-rod levels of antipathy, or even care if I did. “I’m The Type of Guy” was jamming to me. I recall hearing Power 99 premiere this, while riding in the car past City Hall with my Uncle John, on our way back from Philadelphia’s famous open-out-door Italian Market. My purchases that day, were an MC Hammer “Let’s Get It Started” tee, and yet another Black Bart shirt, should tell you where my head was at the time. When we first heard LL say “you’re the type of guy, that wants to call me a punk, not knowing that your main girl’s bitin’ my chunk”, the explosion of laughter in the car made us miss the right turn onto Market Street.

The backlash from this song’s success, and subsequent overlong, spotty album to follow, would later lead to LL having to add counterbalance the next year, in the form of a black-and-white video draped in a hoodie with no chain, inside a boxing ring, declaring “Don’t Call It A Comeback!”. But to a pubescent teen, LL truly didn’t need one. This video would go on to inspire a famous scene from Mission Impossible, while also prophesying LL eventually starring on a CBS TV show, as a ninja-like Navy SEAL.  

“Sippin’ On Some Sizzurp”-Three 6 Mafia, Project Pat, and UGK

We expect some blow back on this selection, particularly from those south of the Mason-Dixon line, because this song is a widely regarded Southern Rap classic. It features two of the region’s most respected rap groups of all-time.

But as someone who only lived as south as Maryland, college graduating age at the time, I’ll keep it a buck for all those who saw this on the list, now giving me that “wassup fool?” look. We Northeast-bred rap fans didn’t know what this was back then. Many still might not, even today. It wasn’t just that it was essentially a four-minute tribute to the joys of codeine cough syrup. That horribly dangerous tradition did, after all, start in Philadelphia. It was the whole package that felt overwhelming. The Chinese-Water-Torture-like beat, which crept along in a different way than Jeru’s “Come Clean”. The hedonistic, mantra-like hook. And who brags about eating so many shrimp, they got iodine poisoning?!? Or pronounces it "I-DINE POY-DU-NIN'" when they do?!?

I recall being in New Orleans for Jazz Fest that spring it came out, laughingly repeating this ridiculous, yet infectious, hook everywhere. It was catchy, but also comedic at the same time. Those college-age/recent-grads of Okayplayery foundation like us, in the early days of the internet, were busy listening to The Roots, Common, or Black Star at the time. Yet twenty years later, I’d be the first to admit that this hypnotizing banger, has more replay value than almost any song Common ever made. And Three 6 Mafia beat Comm to the punch on grabbing a Best Song Oscar by a decade, while The Roots went on to become America’s house-band on The Tonight Show. The way life actually turns out, is usually wilder than any of the hypothetical scenarios we can dream up.