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(from Toure’s baller-ass blog)

KRS-One once told me hiphop songs are like confidence sandwiches. You put them in your mouth (and repeat the lyrics) and they make you feel the confidence of the MC. Much of hiphop is about bragging, either saying I’m so ill with these lyrics or I’m so tough on the street or I’m so good at making and spending money or I’m so smooth with the girls or whatever. I’m all in favor of Black men having bravado and brandishing their outlandish self-esteem, given that there seems to be a multimillion-dollar multimedia campaign to destroy Black self-esteem. Hiphop seems hell-bent on giving us examples of Black men with massive self-esteem. So I’m all in favor of a song like Otis, which is filled brags. It’s a brag session: which of the two wealthy men can say the baddest brag. Let’s go line by line and see which line/brag works and which, in my opinion, doesn’t. I’ve created my own point system based on amateur boxing’s 2-point system. A blah line gets no points, a good line gets 1, a great line gets 2. I’m giving points for writing and delivery, though admittedly a system like this doesn’t give enough credit for flow but that’s something that becomes apparent over time and over an MC’s relationship to many beats, not one. Jay’s flow is obviously much smoother than Kanye’s but the writing and the meanings and the subliminals that come from their pen are so important.

[Jay]
I invented swag
[2 points—In a song full of braggin this is a nicely audacious way to start. Sets the bar high. Sons others who talk about having swag.]
Poppin bottles, puttin supermodels in the cab.
[1—This is a nice brag, I take supermodels out and then get rid of them while you’d be slobberin over them but how am I to take this from a married man? It’d be better coming from Kanye. There’s so many realistic brags here this one strains credulity to me.]
Proof : “I guess I got my swagger back.” Truth .
[1—Clever. They sample Jay from All I Need, a ten year-old song.]
New watch alert: Hublot’s .
[2—This is part of Jay’s I invented swag ish. He’s good for bringing new luxury brands into hiphop’s consciousness. Hublot is a relatively new top-line watchmaker (around only since 1980) and it hasn’t been mentioned much if at all in hiphop. A brag with specificity.]
Or the big face Rolle.
[0—This isn’t much of a brag. Everyone knows Rolex. It’s considered a top-line watch but it’s the opposite of rare. After Hublot, to name-drop a top of line model of a common brand leaves me nonplussed. He probably had a hot Rolex when he got in the game and hadn’t gone much further than Maryland.]
I got two of those .
[0—Good for you.]
Arm out the window through the city, I maneuver slow .
[2—This line may not mean that much but it has a really nice poetic sense, just the words and the imagery—I can see him letting his left dangle out the Maybach window—and the way he says it is fly. Also, this comes just after talking about his watch collection, so saying he’s got arm out the window and is moving slow, because time is on his side, makes it work.]
Cock back, snap back . See my cut through the holes
[2—A triple entendre. First he’s cocked back his hat and you can see his hair cut through the hole of the hat. Also, if he’s cocked back a gun’s hammer you’ll see the cut of his diamonds through the Maybach window’s holes. And, in football terms, you snap the ball back to him and then see him cut through the holes in the field because he’s such a slick runner.]

[Kanye]
Damn Yeezy and Hov, Where the hell ya been?

[0—He’s clearing his throat. He’s been away recording this album. O-k. (He actually hasn’t been away at all in a world where we’re waiting for Dr. Dre, D’Angelo, Lauryn, Jay Elec…]
Niggas talkin real reckless: stuntmen .
[2—I hate this simile structure where you lose the “like” that Big Sean innovated but some, like Weezy, do it very well. Oh wait, this is Weezy and Drake’s thing. Has Kanye used their style to send a shot at them? Birdman is the stunna, which is from stuntin. By gosh I think he is returning fire—Birdman, Wayne and Drake have said little things about Jay and Kanye in recent months. And this is actually a great way of using that style—stuntmen are literally reckless so if you’re talking reckless your mouth is a stuntman as opposed to an actual star. Are there famous stuntmen? Notice how they’re good at concealing their faces as they do the stunts. He’s used their style to diss them and used it better than they do. Damn that’s cold.]
I adopted these niggas, Phillip Drummond ‘em .
[2—Drummond of course is the dad on Diff’rent Strokes, the character who adopted Gary Coleman’s Arnold Jackson. He was rich. It’s kinda obvious how dope this line is, how it sons everyone.]
Now I’m bout to make them tuck they whole summer in .
[2—He’s not going to make you tuck in your chain out of embarrassment about his being way better, he’s going to make you tuck your entire season in and not mention it because he’s going to flyer places in better jets with better chicks, shopping at hotter places and making hotter music. Living well is the best revenge and my whole life is better than yours Young Money.]
They say I’m crazy, well, I’m ’bout to go dumb again

[1—“Bout to go dumb” is some fly ish to say and we all know how hairy things can get when Kanye acts dumb.]
They ain’t see me cause I pulled up in my other Benz
[2—I have multiple Benzes. Much flyer than saying I have multiple Rolexes. Also a nice play on the ancient “you can’t see me” thing which is usually figurative but here, literal—you couldn’t see me because you expected me in one particular Benzo but I have two.]
Last week I was in my other, other Benz.
[2—Oh, no, actually I have three, or more, and you couldn’t see me last week either. Also, “my other other Benz” is also some fly ish to say.]
Throw your diamonds up cause we in this bitch another ‘gain
[0—More throat clearing. The Roc’s in the building. Got it.]

[Jay-Z]

Photo shoot fresh, looking like wealth
[2—Some very fly ish to say and perhaps the thing that could jump off the song become enudring lingo. “Photo shoot fresh.”]
I’m bout to call the paparazzi on myself

[2—A fly brag and a funny one. Jay stays ducking paps but right now he thinks he’s lookin so good he might have to let him know where he is to capitalize on that. But, in typical Jay restraint, he says “bout to” because he’s not actually going to do it.]
Live from the Mercer
[0—We’re recording this at the Mercer in Manhattan. Ok. Though it does locate him in a specific place leading up to the discussion of place in Jay’s next few lines.]
Run up on Yeezy the wrong way, I might murk ya .
[1—I’m still that guy and I’ll protect my little homie if need be. Don’t test me.]
Flee in the G450, I might surface .
[2—I’m still that guy but now I have wealth to help me escape if I need to. The Gulfstream G450 is a tip-top level private plane that’s especially good for long flights. When you’ve absolutely, positively got to flee the country there’s no more stylish way to do it. And his specificity here, name-checking a hot plane that he probably has, is fly.]
Political refugee, asylum can be purchased.

[2—This may be the best line of the song. I have enough money to buy political asylum anywhere. What’s more important than that? What’s a better brag than that? You can buy some stuff. You can buy big toys. Ha. If I needed to, I could go to any number of countries and buy my freedom. The world really is my oyster. Checkmate.]
Everything’s for sale. I got 5 passports I’m never going to jail.
[2—It’s between this and the previous line for line of the song. This of course continues the idea that I can buy anything including freedom, which I’ve already bought an insurance policy on—I’ve already got 5 get out of America free cards so how could I ever get locked up? That’s the peace of mind we’d all love to have. This, in a world where some think going to jail means credibility and proof of something, Jay’s like no, going to jail is wack and I’ve already set myself up so I’m never doing that. Wonder if this is a little shot at a lil someone who recently had to go to jail…?]
[Kanye]
I made “Jesus Walks” I’m never going to Hell .
[2—Of course this line ups the ante of the brag of the previous lines to a supernatural level: I’ve got a post-mortem Heaven guarantee because of my song. If you believe in Heaven and Hell then this is way better than being able to say you’re never going to earthly jail.]
Couture level flow, it’s never going on sale.
[2—Such a fly thing to say.]
Luxury rap, the Hermes of verses .
[2—That’s an excellent description for what Kanye’s doin.]
Sophisticated ignorance, write my curses in cursive.
[2—This is so fly and so Kanye. It doesn’t have to be explained.]
I get it custom, you a customer .
[1—Fly though I’m sure I’ve heard this before somewhere. Um, EPMD?]
You ain’t customed to goin through Customs? You ain’t been nowhere, huh?

[1—He spits this in a fly way but ultimately who’s he braggin to? Anyone who’s anyone in hiphop has been overseas to tour so… ?]
And all the ladies in the house, got ‘em showin off

[0—Huh?]
I’m done, I hit ya up mana-naaaah!
[0—Um, yeah.]
[Jay-Z]
Welcome to Havana

[2—This nicely dovetails with Kanye’s Spanish tomorrow but, more interestingly, nicely fits with what Jay said the last time he was on the mic about being able to flee anywhere and buy asylum. Surely, if needed to flee, Cuba would be a place to go. This is also an interesting reversal—a few lines from now he quotes Scarface and elsewhere on Watch the Throne Jay references Scarface but here he posits the Scarface journey in reverse: moving from America to Cuba as opposed to Tony Montana’s opposite journey. It also nicely sets the scene for the next line. It’s a simple line but there’s a lot set in motion by this line.]
Smokin Cubanos with Castro in cabanas .
[2—This gets a 2 because of it’s potential veracity. I wouldn’t be surprised if Jay has actually has met Castro and I’m certain that if he were to end up buying asylum in Cuba he‘d end up smoking high-quality cigars with Fidel.]
Viva Mexico, Cubano, Dominicano. All the plugs that I know.
[0—Now he’s just name-checking drug dealers in other places he might go to seek asylum? Ok.]
Driving Benzes, wit no benefits .
[1—His drug dealer homies are pushin the same fly cars that Kanye has and they’re getting theirs outside of the system.]
Not bad huh? For some immigrants.
[1—Those dealers aren’t doin bad at all but this line is nada special even though it’s a quote from Scarface. But it does signal the next two lines in which he’s talking loosely about immigration.]
Build your fences. We diggin’ tunnels .
[2—Immigration fences keeping people out? Please. My kinda peeps, my plugs, we can’t be stopped—we’ll just go under your stinkin fence. We go around the man. We’re unstoppable.]
Can’t you see? We gettin’ money up under you.
[2—This borrows shine from the previous line, makes the idea clearer: we’re getting money by all means necessary. Like them, I’m invading the economic system and getting paid and there’s no way you can keep us out. Blacks acquiring wealth is still a revolutionary and powerful gesture and I’m unmoved by arguments that “Jay’s just talking about being rich.” Being a rich Black man has political weight in this country even if he’s not overtly political.]

[Kanye]
Can’t you see the private jets flyin over you?

[1—This is a clever answer to the previous line: our largesse goes over you as our moneymaking schemes go under you. We’re everywhere you want to be.]
Maybach bumper sticker read “What would Hova do?”
[2—The visuality of this line is great: can you imagine a Maybach with a bumper sticker? That’s funny. But the bumper sticker plays off of Jay’s most audacious nickname, Hova from Hovah from Jehovah. He’s Godly and whoever’s driving this Maybach is asking themselves WWHD? Ill. It’s a little ass-kissy, but the Jesus to Hovah connection makes more sense and it’s better that Kanye gave love to Jay here rather than saying What Would Kanye Do?]
Jay is chillin, ‘Ye is chillin. What more can I say? We killin em
[2—Nice play off of Audio Two’s classic Top Billin.]
Hold up, before we end this campaign
[1—I like that he’s saying we’re almost done and more that he posits the song as a campaign, which can mean a series of military operations. Even in the political sense, it’s still a military operation albeit a verbal one.]
As you can see, we done bodied the damn lames

[0—We done did what we set out to do.]
Lord, please let them accept the things they can’t change
[2—He adapts the famous Alcoholics Anonymous prayer and sends his pity to the damn lames—they can’t change that we’re better than them. Can’t they just learn that?]
And pray that all of their pain be champagne/sham-pain.
[2—He ends with a double entendre—let them have celebratory alcohol instead of pain or let their pain be false, sham-pain. I wish them serenity and freedom from their pain. We’re so far above them we don’t even wish them to suffer.]

Who won the song? Well, predictably since they’re working and writing together they’re even: both at 31. (The competitive aspect of this scoring system works better when the MCs aren’t working together on the rhymes.) Looking inside the numbers, Jay has a triple entendre and the two best lines of the song. Can’t say one killed the other.

Rap Genius has Otis explained in layman’s terms as well..