Cleverest turn of phrase in rap/hip hop?

I’ll go with favorites too:

*I’m tryin’ to bring from like recesses in my mind
a word or two that wouldn’t prove unkind.
Aligned as he was with the less-than-angelic,
trafficking black tar smack & psychedelics
in that little-ass van of his, and drunk doing it,
knowing what the right thing to do was but eschewing it,
it’d seem pretty probable
flames are audible: *[…]

hella causing me to wonder if there’s even a point
to our shepherdly tending of his life’s ending.
Bet he’s chilling at Friendly’s
and gonna be back in the neighborhood shortly,
discussing how awesome it is to be portly,
reporting the slant he just got on with Blister
(drank till his wrists hurt,
boned the ghost of your sister). *
~Livin’ at the Corner of Dude and Catastrophe
by MC Frontalot

Wait… nerdcore rap doesn’t count? Damn… Seriously though, in what universe is “boned the ghost of your sister” not an awesome line? The entire song is really made entirely of epic, win, and hilarity.
*Not my favorite musician or my favorite song, hell as a general rule I don’t even like rap, but the title still makes a GREAT location.

‘I’ve never had a dream in my life, because a dream is something you wanna do but still haven’t pursued, I did what I wanted and I did it til it was done so I’ve been the dream that I’ve wanted to be since day one.’

-Aesop Rock - No Regrets

Jragon, hell yes that counts! Weird Al has a classic hip hop song. I give White and Nerdy five mics!

Sway’s lyrics in ‘Little Derek’:
And I been making profits of this my mix tapes raw
Life ain’t always been pretty like nah
On the north side of the city where its gritty like pie
We did what we had to done to get by
Hoping not get caught up in no silly drive-by
Little derek wrote lyrics while the others got high
And he ended up in HMV instead of HMP
Cuz street life could only end one way
Your friend crying on the scene like why, why, why?

I just love that ‘HMV instead of HMP’ line - in case it doesn’t translate, HMV is a music store, HMP is prison.

The Perceptionists
Memorial Day (about the Iraq war)

I never thought of this the day that I enlisted
That I’d be dodging bullets, seekin weapons that never even existed
For someone else’s personal beef, I risk myself
While the Commander-in-Chief, would never come to fight himself
I feel I’m bein’ tricked even worse that the civilians
Nobody ever told me that we would be killin’ children!!
Feelin like the ones that sent me here are the psychotics
but if I say that out loud – I’m “unpatriotic”
but would Donald Rumsfeld back me up with the chrome?
Would Tom Ridge fight or would he stay secure back home?
and would Condoleeza Rice cover grenades in a fox hole?
I’m startin to believe what I was told is not so
What’s the reason for the war?
I’m shootin at these people that I got not animosity for
I wonder if I’m just a pawn in someone else’s struggle
or a here even though I’m just a small piece of the puzzle
I know that when I finally return where I reside
I’ll make up for the months my wife and moms cried
and carry on for all my fallen brothers that died
but you can’t take my pride – cuz I’m a fuckin’ SOLDIER

Does it count if it’s incredibly misogynistic and clever(…ish)?

“They wanna know why I’m so fly,
A girl ask me for a ring, I put one around her whole eye”

Big L - No Endz, No Skinz

“The Wu is comin’ through, the outcome is critical,
Fuckin’ with my style, is sorta like a Miracle
on 34th Street in the Square of Herald
I gamed Ella, the bitch caught a Fitz like Gerald-
-dine Ferraro, who’s full of sorrow
'Cause the hoe didn’t win, but the sun’ll still come out tomorrow.”

Gza - Clan in Da Front

Old School:
Got a bum education, double-digit inflation
Can’t take the train to the job, there’s a strike at the station
Neon King Kong standin’ on my back
Can’t stop to turn around, broke my sacroiliac
A mid-range migraine, cancered membrane
Sometimes I think I’m going insane, I swear I might hijack a plane!

And of course the chorus of that song:

*Don’t push me ‘cause I’m close to the edge
I’m tryin’ not to lose my head
It’s like a jungle, makes me wonder
How I keep from goin’ under *

More from Grandmaster Flash and the Furious Five
A million magic crystals, painted pure and white
A multi-million dollars almost overnight
Twice as sweet as sugar, twice as bitter as salt
And if you get hooked, baby, it’s nobody else’s fault

More recently Kanye West cracked me up with this line:
Now, I ain’t sayin’ she a gold digger
But she ain’t messin’ with no broke niggas

The longer this thread lingers
It seems to me
It just an indictment
How crass hip hop be
Ain’t got no imagination
It don’t speak
Post another one
Bet it is weak…muthafucka.

Don’t need no hateration, holleratin’
In this dancery
Let’s get it percolatin’, while you’re waiting
So just dance for me

I’m blastin, outlastin
Kinda like Shaft, so u could say I’m shaftin
Old English filled my mind
And I came up with a funky rhyme

LL Cool J, “Mama said knock you out”.

Criticising rap and hip-hop for its ‘gangsta’ references, is like saying Hill Street Blues should be frowned on, so with that in mind here’s some street commentary.

*Step to a man wit the clan at hand
In a masterplan, shit, God-damn
Lethal weapon, rhymes are def and
Tim Dog’s a man, you shouldn’t a been sleeping on
I carry on wit the song,
you’re right, I’m dog-gone
Word is born
I’ll compare and dare wit a stare
Your saying where? I’m over here
Rap bull, a guerilla warfare
Dis my crew, don’t you dare
Girls jock me, crowds clock me
While rap artists peer’s cock block me
But if there a rapper that think that he’s better than me
Bring it on, step to me *
Dre beating on Dee from Pump it Up
Step to the Dog and get fucked up
I’m simplistic, imperialistic, idealistic
And I’m kicking up ballistics
Having that gang war
We want to know what you’re fighting for
Fighting over colors?
All that gang shit is for dumb muthafuckas
But you go on thinking you’re hard
Come to New York and we’ll see who gets robbed
Take your jeri curls, take your black hats
Take your wack lyrics and your bullshit tracks
Now you’re mad and you’re thinking about stomping
Well I’m from the South Bronx
Fuck Compton *

Proper gangsta! :smiley:

Then for more thoughtful stuff you check out The Disposable Heroes.

For underground metaphors
You can scrape an inch below the turf, for what it’s worth
My style’s been developed in the core of the Earth
The exhale’s volcanic, the inhale is seismic
So brothers just panic when he Live one arrives with
The natural ability to run through your crew
From 2-1-4 to 2-1-3 to 2-1-2
In other words, from Dallas, to L.A., to the place where J stay
Everyday is mayday

I displays my credentials over instrumentals
And my potential, increases at a rate that’s exponential
It’s detremental questionin my thesis
The penetration’s exact, like amniocentesis
I rip your rhyme to pieces after drainin out your fluid
My vocab is fluent yours is evident of being truant
I know you wanna make moves but son you best to take a second look
Before my knight takes your rook

– J-Live, “Braggin Writes”

"You want problems? well I’ll solve 'em and make examples
I love bustin out crowds so all people get trampled

Spit crowds wit the 4-5
Like when Moses split the tide
Those that froze chose to die

Stay higher than a hello, how you doin?
Burn the rubber till the tires ruin
Burn a coat of fire human

Cause this Drag
Burnin like the grits on Al Green’s back
Causin a switchback"

-Drag-On (an underrated rapper, imo)
on Swizz Beatz’s “Move Right Now”

and another:

“Move out my fuckin way boy you gonna get sliced
I seek revenge upon the earth like Christ
A mind is not called a rapture
It’s more like a rap tour
Where niggas get cornered with a cracked jaw
I divide niggas like religion
End at abandonin’ shit, tellin’ mad lies to your vision
Burnin’ me is invain and imaginary
You must be insane and fuckin’ with mad theories
All niggas gash you, thoughts could match this
Got burnt, and return to mothafuckin’ ashes”

Killah Priest
on DJ Spooky’s Catechism

Joell Ortiz is a beast.

MF Doom is the first rapper I thought of when I saw this thread:

Villain for hire, admire the sound
Make sure The Price Is Right before he come on down!
Rappers be on some, “You you you…!”
Forgot who they talking too, too much pork stew
They need to not come out with nothing new
Blew the whole shit up on some, “What this button do?”
Doom cheat the game like walk-thru
Run 'em, son 'em like Mr. Rourke do Tattoo

I’m sorrii-- I just now reread this and am more convinced that he’s saying “cause its a Swizz track” rather than “causin a switchback”…

It may not be the cleverest, but it cracks me up every time I hear it:

I’m with some nasty hoes,
eating pistachios

davidw, I was going to post some doom, but I couldn’t think of what to post. I knew someone would come in and post something from him, though.

Biggirl, come get your spanking for posting Mary J’s craziness. And, it’s like a jungle sometimes. Sometimes.

ETA: I just noticed why you posted Mary, Biggirl. Great post.

“I love you like a fat kid love cake”

Remember, Nzinga got the message right.

What can I say? I remember how I remember it and not exactly how it was.

I can’t think of a specific example off the top of the head, but I know, I know that the correct answer is something by Biggie or the Wu-Tang. I know it, and I’ll try to find the best example later today.