LL Cool J vs. Kool Moe Dee: So, Who Really Won?

Jun 21, 2006 (Updated Dec 27, 2006)

The Bottom Line Want to know who really won this Rap Golden Age lyrical war between LL Cool J and Kool Moe Dee? It might not be who, oops, sorry...what you think!

Okay, I’m so exhausted with doing my 2Pac series that I’m taking a much-needed break. So while I decide when I can jump back to doing Better Dayz, the Tupac: Resurrection soundtrack, Loyal to the Game and Thug Life, Vol. 1, here’s something to keep your attention:


Got beef?

Diss records just plain suck nowadays. Apart from the now-legendary Jay-Z vs. Nas engagement of 2001, no other lyrical bout over the past decade has really impressed me. That is a shame, because battle rap is one of the traits that make hip-hop music unique and entertaining at the same time.

However, during the Rap Golden Age, which roughly lasted from 1986 to 1993, it was an entirely different story.

Or was it?

The four-year lyrical war between LL Cool J and Kool Moe Dee has always been seen as exemplifying the high level of - and high regard for - lyrical skill in diss records. It is that trait that has been the center of arguments for Kool Moe Dee, his supporters mainly contending that his diss records were technically superior to LL’s. As for LL, well, his proponents merely point to his longevity, which is a sharp contrast with Kool Moe Dee’s sad fate. To this day, there really has been no clear-cut winner announced.

It is a slice of hip-hop history that has occasionally had me bemused. Who really won this lyrical war, LL Cool J or Kool Moe Dee?

Well, let me just say this before I get deeper into this subject: It had less to do with the quality of the records than with something else.


In 1987, the nineteen-year old James Todd Smith – better known as LL Cool J - was the hottest solo star in rap music. No one shone brighter than this guy. He had just released his second album Bigger and Deffer, which received mostly strong reviews and by the end of the year would be certified double platinum by the RIAA. And he had a Top 20 pop hit with “I Need Love,” the first successful rap ballad. He was also the flagship artist of Def Jam, then a fledging company that would soon become rap’s most successful and enduring label. No wonder the guy had such a big ego. In fact, Bigger and Deffer is one of the definitive rap albums of braggadocio. It is extremely difficult to find another rapper before or since who tapped his back more frequently – and harder – than LL.

Meanwhile, a shades-wearing, twenty-four year old rapper stood by the sidelines, apparently disgusted by what he was seeing, and quietly sharpening his talons for the opportune time to strike.

His name was Mohandas DeWese, but he was better known as Kool Moe Dee.

Kool Moe Dee was one bold dude, but perhaps he had his past for inspiration. Just a few years ago he had dismantled local party rapper Busy Bee in a freestyle battle. It was this performance that made him one of the pioneers of the artform. As for LL, he might have thought, who has he ever battled and won? The closest he ever came to a battle was when a female rapper responded to his record about a promiscuous woman, “Dear Yvette,” off his first album Radio. And he didn’t even reply! And he thinks he’s the s**t - what a loud-mouthed punk!

But then again, he might have not thought about Bigger and Deffer’s “The Breakthrough,” which has LL subliminally dissing M.C. Shan in response to “Beat Biter.” Nevertheless there was something that was way bigger than battling per se – it was R-E-S-P-E-C-T.

You see, Kool Moe Dee was a former member of the Treacherous Three, a rap group that is firmly placed in hip-hop’s earliest years, the late 1970s and early 1980s. These guys were first-generation dudes, at a time when hip-hop was nascent and strictly a New York phenomenon. Meanwhile, guys like LL Cool J (and of course, Run-D.M.C.) represented the next generation – the ones who were beginning to define hip-hop music and making the first ventures into the mainstream. Just like how guys like Daddy Kane and Public Enemy are old-school to me, that is how Kool Moe Dee and the Treacherous Three must have looked to LL Cool J. Old school.

But Kool Moe Dee took next-school rappers’ assumed perception of people like him to a different level. He felt that the second generation was brash, forsaking their forebears, taking their style and building upon it while dismissing them as, well, old, quite literally. And the embodiment of such brashness was LL Cool J. As a highly successful and egotistical rapper, he became the perfect target for Moe Dee’s lyrical darts of fury.

It is not really known how LL incurred Moe Dee’s wrath. Some have suggested that the theory that LL Cool J bit his rhyming style eventually convinced him to strike. Other theorized that after expressing his distaste for LL’s big-headedness in interviews and magazine articles at the time, he approached LL and had a chat with him, only for LL to ignore him.

Regardless of the theories, Kool Moe Dee eventually decided that his talons were sharp enough. It was time.

Kool Moe Dee’s second album, How Ya Like Me Now, was released just a little while after LL’s Bigger and Deffer. He gets right down to it in the title track and the first song on the album - "How Ya Like Me Now". In the second verse, Kool Moe Dee makes it quite clear how he feels about the second generation: “new jacks” who are “jock[ing]” his style. He is obviously disgusted with their lack of originality, let alone skill: “What is this, Amateur Night at the Apollo?/Get off this stage!/I'm in a rage!” He also answers to second-generation critics who said that the first generation of rappers was antiquated in their public appeal. “Sucker MCs in the place that said I/Could only rock rhymes, and only rock crowds/But never rock records/How ya like me now?” he snaps in response.

However, it is in the third verse that he increasingly gets more specific. By saying, “I'm Bigger and Better, forget about Deffer!”, it is painfully obvious who he is going after, so in the fourth and concluding verse, he doesn’t even bother mentioning LL’s name – he was only concerned about pummeling this “sucker rapper” running around town “saying he’s the best.” Finally, after Moe Dee had built up the tension in the song, the theme slowly narrowing down to the subject of his wrath, and in between bars that clearly but succinctly pointed to the reasons for verbally attacking him, he gets to rebuke LL - like a scornful parent does a disobedient child.

Make him feel the wrath, beat him down and laugh
And when I’m finished, I'm gonna ask him
”Who's the best?” And if he don't say Moe Dee
I'll take my whip and make him call himself Toby
Whip him good, then I'll make him sweat
Always talking about battles, but he never had a battle yet
But if we ever did, how could he beat me?
He’s so petrified and scared to even meet me!
My word's the law – that's why you don't beef
You're nothing but a punk, track star, and a thief
So I'm putting you on punishment, just like a child
Never touch another mic – how ya like me now?

But that was not the only place Kool Moe Dee insulted LL Cool J. One look at the album cover of How Ya Like Me Now reveals a white Jeep right behind Moe Dee, LL’s trademark Kangol hat crushed under one of its wheels. Yikes.

It was a virtually perfect start to the feud. This caused the hip-hop community to wait in anticipation for LL Cool J’s reply. How was he going to respond to this, from some commercial upstart who felt he was so full of it? Is he even going to respond?

Of course LL’s ego would not let him keep quiet. Almost immediately he unleashed “Jack the Ripper”, and the results are not as good. In fact, it is quite a mediocre diss record. All LL talks about for about 90 percent of the song is how dope he is. Just what everyone needed from him – yet another braggadocio track. I mean, Jesus H. Christ, couldn’t this guy shut up for once about himself and attend to the issue at hand? At one moment, he is replying to Moe Dee’s diss record, then in the other, he just trails off, too gassed up on his own ego to keep the momentum. Pretty ironic, especially when he says, “I won't allow myself to go off track.” Even when he’s more direct, his bars are pretty lukewarm: “How ya like me now, punk? You living foul/Here's what my game is, kill is what my aim is/A washed up rapper needs a washer.” Ugh, horrible. And his best blows – “How ya like me now? I'm getting busier/I'm double platinum, I'm watching you get dizzier” – concerns his commercial, not lyrical, superiority. In fact, judging by the overall laziness of the track, it seems that LL was indeed relying on the success of Bigger and Deffer a little too much, especially considering that Kool Moe Dee was yet to go gold with How Ya Like Me Now, even by the end of 1987.

But that didn’t bother Moe Dee. In fact, that just added more fuel to his fire. The third record in the dissfest, “Let’s Go” was hastily released. This has to be one of the most (unfairly) slept-on diss tracks ever. I mean, my God, Kool Moe Dee rips LL Cool J to shreds on this one! He starts off the song with a reporter asking him, “So tell me, how do you feel about ‘Jack the Ripper’?”, then follows it with a sample of the famous laugh at the end of Michael Jackson’s “Thriller,” at the end of which a distorted voice commands him to “Get him!” And get him he does. It’s five minutes and twenty-five seconds of relentless, non-stop lyrical pugilism, using the support of a hard synth-heavy beat he co-produced to knock down the ladies’ lover to the canvas again and again. There is not one point in the song that Kool Moe Dee halts his verbal attack to give LL Cool J a brief respite. For example, check the way he does damage in the first verse:

Boy, I'm gon’ chew you, ‘cause I knew you
Was talking that junk, punk, now I’ma do you
The way you should be done - call you my son
Make you say "Daddy, I don't want none!"
I've had enough of you acting tough
You huff, puff, grab your stuff, you cream puff bluff
Talk about a battle, but you don't wanna do it
You got yourself into it, you blew it
You egomaniac, I'm a brainiac
You came back with a stone cold plain attack
Jack the Ripper, down with my zipper
You get paid to be a Moe Dee tipster
Tryna knock the way I rock, get off my jock!
I’ma knock you out the box!
Let’s go!

Yep, not only did Kool Moe Dee maintain his claim of LL’s style biting and his annoying ego; he also agreed with me on one thing – “Jack the Ripper” was “weak-wack.” But the most powerful blows would be delivered in the third verse, where Kool Moe Dee employs alliteration – a figure of speech most rappers avoid using - to damn near obliterate his opponent:

Tryna be me, now LL stands for:
Lower-level, lack-luster
Last, least, limp-lover
Lousy, lame, latent, lethargic
Lazy-lemon, little-logic
Lucky, leech, liver-lipped
Laborious louse on a loser's lips
Live in limbo, lyrical lapse
Low-life with the loud raps, boy
You can't win, huh, I don't bend
Look what you got yourself in
Just using your name I took those Ls
Hung 'em on your head and rocked
your bells!


Even being the great bragging lyrical beast that he was, how the heck could LL respond to that? Kool Moe Dee pretty much kicked his a*s, some thought for good! “Let’s Go” is simply a diss record of high technical skill, the best of the five-round war between them. 1987 ended without a response from LL Cool J. In fact, it would take him two years to respond. It only added to the belief that Kool Moe Dee won the battle, although it might have been a wise move on LL’s part. The next three years were not exactly the best ones of his career. Already he was receiving a backlash in an industry that was transitioning into African medallions, socio-political consciousness, and gangsta rap. LL Cool J, who must have seen Kool Moe Dee as old news, now must have looked the same way to cutting-edge performers like Public Enemy, Boogie Down Productions and N.W.A. Releasing Walking With a Panther, a decidedly boisterous and bloated affair, in 1989 did not exactly help matters, either.

Meanwhile Kool Moe Dee, who had always made socially conscious raps, fit in perfectly with the changing times in rap and became a star in his own right. By the end of 1988, How Ya Like Me Now was certified platinum, and his third album, Knowledge Is King, quickly went gold. While he became the first rapper to get on stage to perform at the Grammys, LL was being booed off stage at the Apollo Theater. Amazing how some things change, huh?

Well, LL Cool J was definitely down, but not out. It was when he made a critical and commercial comeback with 1990’s Mama Said Knock You Out that he decided that it was the right time to reignite the feud. “To da Break of Dawn”, originally published in 1989, was his response to “Let’s Go”, but by then the hip-hop community had either grown tired of the conflict or thought that Kool Moe Dee had won due to the lack of an immediate response. It didn’t seem to matter to LL Cool J, though. This time, his verses are a lot more inspired, cleverly mixing his denial of Moe Dee’s rhyming skill and claim of style biting with his mainstream appeal:

Wouldn't bite because your rhymes are puppy chow
Made another million, so competitors bow
Homeboy, hold on, my rhymes are so strong
Nothing could go wrong, so why do you prolong
Songs that ain't strong, brother, you're dead wrong
And got the nerve to have them Star Trek shades on
Huh, you can't handle the whole weight
Skin needs lotion, teeth need Colgate
Wise up, you little burnt-up French fry
I'm that type of guy!
When I'm through, you need a brand-new identity
I was scooping girls before you lost your virginity

Unbelievable. How could a rapper supposedly out for the count arise from the canvas and declare that he’s far from done? That had to be initially demoralizing to Kool Moe Dee, especially considering that Mama Said Knock You Out was a great success, winning him a Grammy for the title track. By the time Kool Moe Dee was preparing to release his fourth album, Funke Funke Wisdom, in 1991, LL’s comeback record was approaching the double platinum mark. Once again LL Cool J was the biggest solo act in rap - save for M.C. Hammer, of course. Moe Dee was virtually back to where he started.

LL Cool J’s resurgence apparently didn’t bother him, because he ended up including “Death Blow” - the fifth and final record in the feud - in his album. He did give it his all. Once again, he uses alliteration, and you can feel his voice rise higher in volume until it hits a furious climax:

Low-life loser, life like luna
Lackadaisical, lipless luna
Tic liver lifeless, living likeness
Lusting, longing lyrics like this
Little league, lard, larcenist, liar
Label ledger, left the leper liar
Bull, lull, lateral learning
Laps, language, latent, lurking
Language, language, local logo
Light-laboring, limited, local
Now LL's a laughing stock
'Cause I bit that a*s to the last stop!

Nice try, but there were a couple of things wrong this time. First off, who really cared about this feud anymore? Secondly, Kool Moe Dee kept on repeating the claim that LL stole his style throughout the entire song. “You still got a lock on my jock like a pitbull”? Come on, Moe Dee! We know already - you told us that in “Let’s Go”. I mean, tell us something we don’t know. Thirdly, Kool Moe Dee has a bad case of denial. Sorry, sir, but when you say stuff like “Marley Marl can’t save you from falling” and that “[LL Cool J’s] records ain’t hot,” that could not be any further from the truth, as the production work of the legendary producer was one of the main reasons for the phenomenal success of Mama Said Knock You Out. Fourthly, even the alliteration is not as clever as before – he uses a few words he had used for “Let’s Go”, two couplets rhyme the same words, and there are words and phrases that fail to hit the mark simply because they do not make any sense. Fifthly, the whole affair gets pretty boring, clocking in at seven minutes.

But the biggest flaw in “Death Blow”, it seemed, was its production. Throughout the eighties the rap industry pillaged James Brown’s catalog so often for beats it got pretty annoying. In fact, both “How Ya Like Me Now” and “Jack the Ripper” contained samples from the Godfather of Soul. But by 1991, James Brown sampling had played itself out; in fact, rap consumers developed a strong aversion to any beat constructed from his work. So when it was discovered that Kool Moe Dee was rapping on yet another James Brown-sampled beat, many turned up their noses in disgust. Eww.

No one was buying it, literally. While Mama Said Knock You Out cruised past the double platinum mark, Funke Funke Wisdom cruised past…double wood. So while hardly anyone might have heard about “Death Blow”, more than two million customers definitely heard “To da Break of Dawn”. In fact, I can picture a couple of them, hardcore followers of the lyrical feud, laughing at the barb about Kool Moe Dee’s trademark – “’And got the nerve to have them Star Trek shades on’! A-ha-ha-ha! That s**t is funny! Ha-ha!”

Kool Moe Dee could have kept his mouth shut and ignored it, but maybe he wanted to have the last word in the war of words. Noting that LL Cool J opened himself to disses by other rappers for not responding duly to “Let’s Go”, he must have not wanted to look like a punk. Whatever. Kool Moe Dee’s career was never the same after that. While LL Cool J blossomed into the exceptional symbol of longevity in a notoriously fickle musical genre, Kool Moe Dee’s star faded fast. He would have his Greatest Hits released in 1993, a sure indication that he was no longer commercially viable. Then in 1994 he reunited with his Treacherous Three brethren to release Old School in February, and his fifth solo album – Interlude – followed in November. All three albums bombed. The title of his latest album was befittingly meiotic – it has been an interlude that has seemingly gone on forever, because close to nothing has been heard of Kool Moe Dee on the musical tip ever since.


It was 1998, seven years after the last record of LL Cool J vs. Kool Moe Dee was released. Once again LL, by now a thirty-year old veteran with seven albums under his belt, was being challenged – by some scrawny-looking dude with a penchant for dropping razor-sharp and battle-ready bars. Coincidentally, this young man, whose name was Canibus, was the same age as Kool Moe Dee when he started his lyrical feud with LL – twenty-four. Like Kool Moe Dee, he would give LL a severe a*s-whooping with the first diss record of the feud, "Second Round K.O." Like he did with Kool Moe Dee, LL would retaliate by dropping an inferior reply, the befittingly titled “The Ripper Strikes Back.” And just like Kool Moe Dee, Canibus would suffer the same demise. To sum it up, discounting the legendary status of LL, Canibus simply did not have the commercial leverage his opponent had. History repeated itself, I guess.

Which finally brings me back to my question: Who really won this lyrical war, LL Cool J or Kool Moe Dee?

Well, let me end this essay by saying this: It wasn’t LL Cool J…

…but it wasn’t Kool Moe Dee, either.

No, my dear friends, the true winner of this war has a name that starts with an “s.”

And no, it’s not “Superman.”


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