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written by Sam Greenspan

A deep dive into Jay-Z’s 99 Problems lyrics to figure out which problems are more severe than others.

I was listening to 99 Problems by Jay-Z today… you know, because I’m hardcore, but seven years behind… and, in the middle of the verse where he tells a long story about outsmarting a cop who pulled him over, it dawned on me. For a song called 99 Problems, he really doesn’t detail very many of those problems.

So I deconstructed the lyrics like a Top Chef contestant deconstructing a quiche (here’s some sauteed spinach with a piece of gouda sticking out of it and a cube of dough). And, as luck would have it, I dug out exactly 11 problems listed in the song.

And no, I didn’t count him saying “I ain’t passed the bar” as a problem, as I am assuming this was a hypothetical and Jay-Z didn’t actually graduate from law school in the early ’90s then fail the bar.

And here they are, ranked from most severe to least severe.

1 | “Foes that wanna make sure my casket’s closed.”

This is clearly the biggest problem he’s facing. Jay-Z is a beef magnet. He’s like the opposite of a Clara Peller sandwich. Jay-Z’s had many highly publicized beefs over the years — Nas, Mobb Deep, The Game, Beanie Segel, 50 Cent, MC Hammer, Noel Gallagher from Oasis, 2Pac. Yes, I still consider 2Pac as a threat to Jay-Z, and he should too. If Jay-Z’s ever doing pottery and feels like there’s another set of arms wrapped around his.

2 | Having to strong arm a ho and then “get[ting] trapped in the kit kat again, back through the system with the riff raff again.”

According to the Internet, “kit kat” in this case is slang for a police car. I’m not sure how they get that out of “kit kat”; sometimes when I hear slang terms like that, I’m like, “Give me a break.”

As for why this ranks so high? Jay-Z’s living the hundred-millionaire’s life now. He doesn’t want to end up getting arrested and thrown in a police car. And then, on top of that, to have to go into jail and be surrounded by commoners. The horror! I mean, how many other guys in that jail are banging a former member of Destiny’s Child? It can’t be more than five or six.

3 | “D.A. tryin’ to give a n***a [the] shaft again, half-a-mil for bail ’cause [he’s] African.”

I think he can make the $500,000 bail, but that’s still a lot of money to put together quickly, what with daily ATM limits and all. And this problem ranks high because the D.A. really would have it in for someone this famous. If they were willing to plant evidence and set up OJ, they’d definitely be willing to do the same to Jay-Z.

4 | “Paparazzis with the[ir] cameras, snappin’ [photos of him].”

This is definitely a problem. Prophetic of him to recognize it in 2004, back before the celebrity gossip blog explosion. Just imagine how he’d feel about the paparazzi if they ever captured a photo of him having a nip slip. Or one where his belly’s pushed out a little and they all speculate he’s pregnant.

5 | “Rap critics that say he’s ‘money-cash-hoes’ — [he’s] from the hood, stupid, what kind of facts are those?”

I think critics are justified to criticize someone whose rap features a making money:misogyny:actual content ratio of 2:1:0. It’s like criticizing that Lil’ Wayne and his old crew were called Cash Money Millionaires. That’s an astounding redundancy rate. It’s like a Japanese game show loading up words like “super happy terrific very good” without actually revealing that it’s a game show where people throw scorpions at each other’s penises.

6 | “Fiends on the floor, scratchin’ again.”

I put this one right in the middle of the list because I honestly have no idea what the hell it means. So I can’t speak to the severity.

7 | People not “understand[ing] the intelligence that Jay-Z has.”

It’s always so frustrating when people underestimate your intelligence. He’s worth somewhere between $150 and $500 million AND kept his street cred after putting out a song where he samples Hard Knock Life from Annie. When he raps about getting brains, there’s a more-than-usual chance that he’s actually talking about knowledge.

8 | “Rap mags tryin’ to use [his] black ass, so advertisers can give ’em more cash for ads.”

I’m not exactly sure why he’s so bent out of shape about this. The magazine business is very simple. You pose for the cover, get publicity, feel like a big shot — we sell the issue and take in advertising revenue. And then go out of business anyway.

9 | “Radio, if I don’t play they show, they don’t play my hits.”

This problem gets pushed down because I don’t think it’s credible. I know the radio stations all love their concerts (“Come out to 98.3 The Pig’s Oinkfest ’02”) but I can’t see them outweighing the value of playing a artist’s music. It’s almost like Jay-Z is grasping at straws to try to get to 99 problems. (And I can sympathize. When I’m writing on this website, sometimes it takes a lot of finessing to get to 11. If I was trying to do nine times that, I’d never get done. All of my lists would be, like, “99 Best Numbers Between One and 100.” And 71 would totally get the shaft.)

10 | Feeling bad for you, son, because “you’re having girl problems.”

All of the problems enumerated above are ones that externally effect Jay. This problem deals with an empathetic struggle festering within him. Hard to really believe he’s sweating it too much.

11 | Getting pulled over for “doing fifty-five in a fifty-fo.”

This problem ranks the lowest because Jay-Z was able to find an elusive 54-mile-per-hour speed limit zone. Suggesting to me he’s living in a mythical place like Shangri-La or Parts Unknown. And when you live in a secret utopia, troubles tend to melt like lemon drops.