Staff Top 10
Top Ten Most Conflicted Rap Songs Ever



one thing I want to make clear about this list is that I may be poking some serious holes in these guys by holding them to their dubious words, but I’m not using it as a qualitative scale. Most of these rappers and songs are great, even classic, and I’m just trying to point out that some themes are too big for even the best to keep straight. Inconsistency in hip-hop’s lyrical content does not denote an inherent flaw with the genre. No other style of music, past or present, has thrust into the limelight what exactly happens when success grapples with a Darwinist mentality. They’re all drooling for their shot, and at all times they need to keep a foot in their neighborhood, an arm out to the universe, and don’t forget they want to put their tiny mark on history, too. And anything they say has to rhyme with something else.

This balance is impossible to maintain of course, which is why so many rappers’ careers halt dead once a slip is apparent (stand up T.I., Ja Rule, DMX). But it’s great to see what kind of tongue-tied desperation their brains spill when they try to keep it all together, especially the latter-day Kanye and hungriest Slim Shady. Plus, they’re all human (even Game), and these kind of open-letter contradictions are arguably what make them interesting at all (especially Game), and will make for lovely time capsules in any measure. Roll it.

10. KRS-One – “100 Guns” (1990)

For a so-called “Teacher,” KRS-One is so transient in his philosophies that Robert Christgau was compelled to write “An Autodidact’s History” of him for his Grown Up All Wrong book just to find out how much he (or anyone) could believe what he says. His heart’s usually in the right place, even on a bizarre tale like “13 & Good,” a warning that statutory rapists might get fucked by the law. But for all his “Stop the Violence” pleas toward rap-on-rap crime and pre-Rodney King exposés of police brutality, even calling out “Black Cop[s],” he failed to meet his own concept halfway on “100 Guns.”

Trying to flip his familiar concept of corrupt law enforcement, he tries to play the criminal in pursuit, an illegal weapons dealer, and connect the moral at the end that any confiscated firearms of his will just get sold back to the streets by the indecent cops anyway. But it’s hard to sympathize with his supposedly lesser evil when his cops ring too much of caricature (sample dialogue: “You passed county line / Niggers in these here parts now is a crime”) and the only assurance we get that they’re corrupt at all is KRS’ perp’s own speculation at the end. Problem is, he just shot two (shoddily scripted) cops, so it’s a bit hard for even an authority-hating listener to sympathize. Is it possible for a fictional character to ruin his own credibility? The failure’s a noble one, but it’s the rare instance where a KRS-One interview would’ve been a stronger podium for his suspicions than the song.

09. Nas – “Ether” (2001)

Inspired by Jay, Nasir Jones stamps nearly a decade of missteps and half-steps down under the carpet like all he needed was someone to shoot him a dirty look and he’d end all that Puffy nonsense. Hey, he said it, not me: “Heard it when I was asleep / That this Gay-Z and Cockafella Records wanted beef.” Guy had me thinking sleep was the cousin of death and here he’s admitting Nastradamus was all just a bad dream anyway. Nas really does bring the fire here (though compared to “Takeover,” it might as well be Curtis jockeying for Graduation’s spot), but per his overblown nature, he tends to miss the obvious and kind of plays himself each time he nets a dunk. To wit: “How much of Biggie's rhymes gonna come out your fat lips?” seems to forget that mere stanzas ago he placed himself in Mount Rapmore (“Who's the best? Pac, Nas and Big,”) and derided Jay’s lack of humility for doing same (“Oh, I get it, you Biggie and he's Puffy”).

He might’ve scored harder at preempting some truth behind “Moment of Clarity,” (“you traded your soul for riches,”), if his own Puffy-featured video crucifixion and string of, shall we say, irresponsible albums didn’t catch him in the same act. Most bizarre of all is his lone invocation of the word “women,” to accuse Jay of disrespecting such, before returning to “I rock hoes” bull right after. Not that 2004’s “The Makings of a Perfect Bitch,” is any less romantic because.

08. Ice Cube – “Black Korea” (1991)

The only song on this list that’s flat-out vile, without merit, Ice Cube fans can be forgiven if they were even bummed out most for its sheer pointlessness. Coming off an oeuvre-deepening Boyz N The Hood role and a gleefully inflammatory consumer object named Amerikkka’s Most Wanted, Cube, like namesake-sharing Ice-T, rose to the top of the hard-rap free speech game in 1991 like he was readying some big statement, and out shat Death Certificate, an even more gleeful inflammation with embalmed Uncle Sam on the cover. Except this inflammation in particular was more like a hemorrhoid.

Not to call the pot kettle, well, black, but who throws around titles like Amerikkka while threatening a “nationwide boycott” of “chop suey-ass” Korean shops, with their “Oriental one-penny counting motherfuckers,” because, what, Cube couldn’t understand the guy at the counter? Not that Ice Cube was hiphop’s reigning intellectual at the time or anything, but I’m pretty sure any idiot who’s seen the thing knows the Do the Right Thing bit sampled at the beginning wasn’t scripted in its original context to promote racism. Actually appeals to a lower common denominator than Are We Done Yet?

07. Common – “Dooinit” (2000)

This one made the list as soon as its perpetrator started taunting “a soft nigga on a hard track.” So spat the beret-festooned, vegetarian, token rap entry on Blender’s list of all-time “biggest wussies.” The conscious rapper known for his woman-friendly backpack jams and collaborations with neo-soul sirens was even prescient to satirize his milquetoast image, pre-Wayne Brady/Dave Chappelle, on the same album’s skit preceding “A Film Called (Pimp).” But somehow he felt the need to put down the Gardenburger and come hard here with more than a few ridiculous claims: “My train of thought is that of a hustler,” “I catch him on the streets, in front of the bodyguards and rush him,” (yeah, right) and the short-lived credo, “Don't fuck with radio, ignoring the charts,” on an album followed by a Neptunes team-up, a top 20 debut, and a #1 debut.

Weirdest of all, the former Lonnie Lynn (Blender already mentioned this, but lord, that’s a girly name) criticizes rappers who bit their thug look from Pac, right before arguably the lamest tough-talking insult in rap extant: “in a circle of faggots / your name is mentioned.” Jesus, Lonnie, not even a “in a circle of faggots you suck all their dicks” or anything? “Your name is mentioned.” It’s an embarrassing capper on an otherwise appealing song that fantasized toughness harmlessly up until. Messier yet: Common has since gone on Oprah apologizing for all of rap’s bitch and ho talk in the wake of Imusgate, but still drops the dud “Brokeback niggas,” on his “cleaned-up” album. Dude has some things to sort out and I don’t mean a hamper of dirty sweater vests.

06. The Game – “Doctor’s Advocate” (2006)

It’s no secret that Game’s Doctor’s Advocate is obsessed with all things Chronic, after the Doctor who abandoned him on 50 Cent’s request, granting him an album title, concept and instant underdog status to fuel chatty bloggers. Game’s penchant for name-dropping only makes the constant references to Compton, Shady/Aftermath, Eminem, and Dre himself seem all the more mocking. From the taunts of “Let’s Ride” to the flat-out threats on “One Blood,” the album pretty consistently dresses up in fake N.W.A. clothing to rankle his former sole benefactor with the idea that even after cutting off his blackballed offspring, Dre will promote his record, willing or not.

So it’s more than a little bizarre when the title track no less, switches up the hostile atmosphere entirely for a big soppy reconciliation plea. “Dre, I ain't mean to turn my back on you / But I'm a man and sometimes a man do what he gotta do,” I can understand, but “You still my homeboy Doc / I'd take a bullet for you,” is a little far, don’t you think? This is the same stalker who whispers “Dre…I see dead people,” elsewhere on the record as a statement of intent. And wait a minute, who’s he talking about when he says, “I'm not askin' you to take my side in the beef?” Dre? On “One Blood,” He explicitly says, “I ain't got beef with 50,” on “One Blood.” And his reasoning’s as jumbled as his rhyme; the full couplet goes, “I'm not askin' you to take my side in the beef/ But you told me it was okay to say ‘Fuck The Police’.” Game, baby, you yourself said “Hate It or Love It.” But you still have to pick one.

05. Kanye West – “Can’t Tell Me Nothin’” (2007)

In a trick I wish Eminem still knew, Kanye remains a master of calling himself on his impulsive shit after he pulls it repeatedly, over and over again. Nonetheless, rap-as-church-confessional makes for excellent soul-searching, particularly when you’re as funny and self-deprecating as ‘Ye: “I feel the pressure, under more scrutiny / And what I do? Act more stupidly.” And after verses bemoaning the jewelry addiction he couldn’t quit even after “Diamonds From Sierra Leone,” and his inability to read televised interviews as anything more than one-on-one conversation, he still delivers hilarious stubbornness in the chorus: “Excuse me, is you sayin’ something? Ah ah / You can’t tell me nothing.”

He may be as difficult as Britney Spears, but we can count on greatness like this to emanate from his self-abuse trips, not rehab stints, so let him yammer. Promise of more to come: shut out from any moonman trophies after performing his ass off not once, but nightlong in a hotel suite at this year’s VMAs, he gave the press another tantrum and hopefully a joint as amazing as this for the fans in 2009.

04. Jay-Z – “Moment of Clarity” (2003)

In a move that angered some of his fans as surely as Insane Clown Posse revealing their final sixth joker card was God, the greatest career rapper chose the climax of his reign to utter this bizarre confession: “Truthfully, I wanna rhyme like Common Sense.” He confesses he “dumbed down,” for his audience out of his fear of not moving five mil. Yes, with the world watching, nine platinum or multi-platinum records in, footholds in the biggest producers buyable (Kanye West, the Neptunes, Just Blaze), Cristal-poppin’ Jay stood on the diving board, ready to retire with his final Triple Lindy, and confessed his admiration for stop-smokin’ stop-drinkin’MC Talib Kweli.

I can understand that he felt a pang of guilt for putting out “Parking Lot Pimpin’” after “Parking Lot Pimpin’” rather than using his fame and wealth to rally the community like Pac supposedly did. But being too scared to risk it because “skills [don’t sell]?” A better title would’ve “Moment of Cynicism.” We may never know what he might’ve done with Kweli’s virtues at the peak of his rhyming powers—Katrina damage assessment “Minority Report,” appeared only after the well dried. If Kweli made the inverse confession, a secret vice to rhyme like the carefree, arrogant Jay, now that would’ve been exciting.

03. Public Enemy – “Welcome to the Terrordome” (1989)

“I got so much trouble on my mind!”

Chuck D means just as well as KRS-One, but takes bigger risks and as a result, falls on his face harder when he fails; it takes serious talent to make a song still considered classic and influential despite an unmistakable clunker like “Farrakhan’s a prophet I think you ought to listen to.” His inner struggles and public personal battles were epic back when Eminem was still getting his ass kicked by D’Angelo Bailey, and “Terrordome” remains the most tremendous self-examination the genre’s ever seen. I’m not just talking about the lyrics: The horn intro from T.S. Monk’s funk-nugget “Bon Bon Vie” finds its true home setting off the viral smoke-alarm throb that mesmerizes and headaches for all five and half minutes of Chuck’s damnation on this landmark cut.

The song’s less of a conflict in itself than a response to all the rumors and truths of P.E.’s dreadful years following Nation of Millions, when Professor Griff attached an anti-semetic stigma to the group that Chuck tried to defend out of loyalty to his childhood friend but just had too much heart to maintain was anything other than bullshit. He almost broke up the group entirely, but instead kicked out the fool and encapsulated the tug of war in song (“Never be a brother like me go solo,” “Shouldn’t be suicide”) and laid down some hard lessons he learned in the process (“As for now I know how to avoid the paranoid,” “Never question what I am God knows / Cause it's coming from the heart”).

But even his resolutions provoked furor, because at best, the lines attributed to the Griff incident are cryptic and ill-worded (“Crucifixion ain't no fiction/ So called chosen frozen/ Apology made to who ever pleases /Still they got me like Jesus”) rather than flat-out blaming the Jewish media for coaxing a disturbing ideological flaw from his ignorant friend. But even then he concludes, “It's weak to speak and blame somebody else/ When you destroy yourself!”

As responsible and irresponsible a song reconciling the public with the personal has ever been. Those rappers who’ve spoken out in the wake of Imus should be so frighteningly open about how they really feel.

02. Eminem – “Criminal” (2000)

Where to begin with Eminem? I could’ve picked “Cleaning Out the Closet,” in which he apologizes to his mom for 3/4 of the song before taking it all back with a storm of accusations that ends proclaiming himself “dead to her,” or “White America,” his knowing ode to the hand that fed him the extra 10 mil Hot 97 alone couldn’t provide, or I could’ve picked “Ass Like That,” where the guy who made his career on killing LFO and ‘N Sync whines about the free-speech privileges of a fucking puppet. Every one of those is a great song and every one is also so full of shit you could grow truffles from them. But in a career just begging for psychological and satirical analyses, I picked Marshall’s very own “Terrordome,” an oft-misunderstood ramble of everything personal, political and trivial going through the psyche of the time’s most gifted entertainer at his white-hot peak.

Closing his fiery, parent-obsessed Marshall Mathers LP, “Criminal” begins with a warning that tests the listener before it’s even through commencing: “A lot of people think that what I say on records or what I talk about on a record, that I actually do in real life…or that I believe in it. Or if I say that I wanna kill somebody, that I'm actually gonna do it. If you believe that, then I’ll kill you.” It’s startling the first time you hear it, even if you’re already eighteen deep on a record that began with “Kill You,” a promise to rape his grandmother, among other hilarious empty threats.

But the disclaimer still went ignored by testy critics who seized on the evidence that followed: well-publicized attacks on gays, but also a joke on Versace’s assassination and indictment of preachers. “Criminal” was about nothing, of course, just a laundry list of offensiveness daring you to blink. The song didn’t break its own promises anymore than Marshall Mathers actually killed anyone, it just proved its own point about how foolish people are when they don’t read the fine print. Ironically, it garnered media notoriety that escaped Queens of the Stone Age’s controlled substance valentine “Feel Good Hit of the Summer” and Steely Dan’s underage three-way “Janie Runaway,” both released the same year—without disclaimers attesting to their falsity.

01. The Notorious B.I.G. – “Suicidal Thoughts” (1994)

Possible misconception: that rappers are all unaware of the blurry line they walk, with their shit-talk one minute and pray-to-God the next. Not everyone here is so unenlightened, as this classic Biggie joint knows sadly, prophetically well. Ready to Die cast Big as the Punisher of rap (the literal Big Pun, unfortunately, didn’t fit the profile), dealing with death and violence on an everyday basis, fully prepared to lose if the time to win has ended.

For every “Gimme the Loot” success story of riches and bitches in which to soak for another day, there’s a “Ready to Die” to repent for it once the wrong guy talks or the feds show up. “Suicidal Thoughts” more than falls into the latter—it’s a jaw-dropping confession you’ll never get from 50 Cent. “When I die, fuck it / I wanna go to hell / I'm a piece of shit, it ain't hard to fuckin' tell,” concludes the career criminal, who, no matter how charming his zest to someday own a Sega Gensis was, no matter how pickle juice drinkin’ his lovely ladies know him as, deep down knows it was pretty goddamn mean to threaten that pregnant woman with a two-point blank.

He knows he doesn’t deserve our sympathy; all the breast cancer in the world won’t make it any less foul to cheat on your baby’s mama with her sister. So he went to Hell. But Biggie was so great I hope they at least have black Timbs.

Special irony award for 50 Cent’s “I Get Money,” the man’s first sign of awareness that he is no longer the underdog, which hit the streets just as the record sales stopped rolling in.


By: Dan Weiss
Published on: 2007-10-19
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