I feel like I have an adequate working knowledge of most artists considered among the greats. I own or have owned albums even by performers I don’t care for, such as Neil Young and Joni Mitchell.
But it occurred to me recently that I have absolutely no familiarity with the man many critics and fans consider the greatest rapper of all-time — Jay-Z.
To be fair, my knowledge of rap in general is quite limited. Eminem is the only rapper I follow album by album, and beyond that I have records by Snoop Dogg, Childish Gambino, Outkast and Public Enemy.
In addition to Jay-Z, I am equally in the dark about greats such as Nas, Notorious B.I.G. and Tupac. But Jay-Z is such a cultural icon, in both the past and present tense, that his absence from my radar feels like the biggest oversight.
This week, I will feature five of Jay-Z’s best songs (more on how I settled on this lineup in a bit). I hope to educate myself, understand the hype, and maybe even discover some new music I’ll actually listen to from time to time.
To narrow this list down to these five, I used the highly scientific method of Googling “best Jay-Z songs.” That query returned a huge number of sites, so I picked six reputable music sites and scanned their lists. I set aside the titles that showed up in the top five or ten of all the lists. (Note: I have not included ‘Empire State of Mind,’ which shows up on most of those lists, because I have already featured it on the blog)
My plan for evaluating these songs is to read the lyrics of each before listening and then give my take on both the literary and musical merit.
I’m starting with the Jay-Z song I know best, at least by reputation. I’ve heard references to ’99 Problems’ for years but I believe I’ve never heard the original song. Here goes…
Great song, lyrically. I love the second verse, describing a random police stop for going “fifty-five in a fifty-four.” Interesting how the verses go from professional anger at critics and radio stations to more personal issues with the police and street rivals.
Jay-Z has said that the “bitch” in the chorus refers to a police dog, a questionable claim given the juxtaposition with the mention of “girl problems” in the previous line. The second verse does support his assertion, as the cops threaten to bring in the K-9 patrol, but I see that as a double meaning, not the only one. Jay-Z in fact adds a third meaning in the final verse, discussing not backing down from a fight because of all his problems, “being a bitch ain’t one.”
Musically, the song reminds me a bit of the Beastie Boys’ ‘Fight For My Right to Party,’ with the repeated grungy guitar riff. The propulsive beat (sampled from a Billy Squier song) nicely complements the rapping. I can see why this is a favorite.
If you’re having girl problems I feel bad for you, son
I’ve got 99 problems but a bitch ain’t one
[Verse 1]
I’ve got the Rap Patrol on the gat patrol
Foes that wanna make sure my casket’s closed
Rap critics that say he’s Money, Cash, Hoes
I’m from the hood stupid, what type of facts are those
If you grew up with holes in your zapatos
You’d celebrate the minute you was having dough
I’m like fuck critics, you can kiss my whole asshole
If you don’t like my lyrics, you can press fast forward
Got beef with radio if I don’t play they show
They don’t play my hits, well I don’t give a shit, so
Rap mags try and use my black ass
So advertisers can give em more cash for ads, fuckers
I don’t know what you take me as
Or understand the intelligence that Jay-Z has
I’m from rags to riches, niggas I ain’t dumb
I got 99 problems, but a bitch ain’t one, hit me
[Hook]
[Verse 2]
The year is ’94, in my trunk is raw
In my rearview mirror is the motherfucking law
Got two choices y’all, pull over the car or
Bounce on the devil, put the pedal to the floor
And I ain’t tryna see no highway chase with Jake
Plus I got a few dollars, I can fight the case
So I, pull over to the side of the road, I heard
“Son do you know why I’m stopping you for”
Cause I’m young and I’m black and my hat’s real low
Do I look like a mind reader sir, I don’t know
Am I under arrest or should I guess some more?
“Well you was doing fifty-five in a fifty-four
License and registration and step out of the car
Are you carrying a weapon on you? I know a lot of you are”
I ain’t stepping out of shit, all my paper’s legit
“Well, do you mind if I look around the car a little bit?”
Well, my glove compartment is locked, so is the trunk in the back
And I know my rights, so you gon’ need a warrant for that
“Aren’t you sharp as a tack
You some type of lawyer or something
Somebody important or something”
Well, I ain’t passed the bar but I know a little bit
Enough that you won’t illegally search my shit
“Well we’ll see how smart you are when the K9 come”
I got 99 problems, but a bitch ain’t one, hit me
[Hook]
[Verse 3]
Now once upon a time, not too long ago
A nigga like myself had to strong-arm a ho
This is not a ho in the sense of having a pussy
But a pussy having no goddamn sense, try and push me
I try to ignore him, talk to the Lord
Pray for him, but some fools just love to perform
You know the type, loud as a motorbike
But wouldn’t bust a grape in a fruit fight
And only thing that’s gon’ happen is
I’m-a get to clapping and
He and his boys gonna be yapping to the Captain
And there I go, trapped in the Kit-Kat again
Back through the system with the riff-raff again
Fiends on the floor, scratching again
Paparazzis with they cameras, snapping em
D.A. try to give a nigga shaft again
Half a mil’ for bail cause I’m African
All because this fool was harassing them
Tryna play the boy like he’s saccharine
But ain’t nothing sweet bout how I hold my gun
I got 99 problems, being a bitch ain’t one, hit me
[Hook]
[Outro]
You crazy for this one, Rick!
It’s your boy
Meet Me In Montauk 
I agree the use of bitch refers to a woman along with other clever twists in meaning.
I’ve heard the chorus of this song and have also heard variations covered by other artists, but, like you, this was the first time I have heard the whole song from beginning to end.
From the little snippets I had heard from Jay-Z, I too didn’t get the hype, but listening to his rap here, I am starting to see why he gets praise.