_Jay-Z and Kanye West have built gargantuan fan bases over the past couple of decades because their music was undeniably great. Jay-Z’s universally lauded flow and street-centric realism had a lot of people calling him the best rapper alive in the mid 2000s. We loved Kanye's music for its realism too. His reality was much different than Jay’s, but almost every track off The College Dropout (and most of his popular songs sense) dripped with emotion. We used to love their music because it was real. The gold plated, Maybach dismantling, designer name dropping sounds and sights from Watch The Throne clearly represent the reality in which Jay and Kanye currently reside. But it’s clear that this reality is far removed from that of their fan base. It’s baffling that the album was received as well as it was by most fans. I guess it’s a testament to the...power (if you will) of these two artists. The expense of the samples used has been well documented, and it’s hard to argue against the quality of the production. But two legends trying to out-ostentate each other over gaudy back tracks shouldn’t constitute coolness. There is a fine line between braggadocio and douchebaggery. We'll soon take a deeper look at a few quotes that surpassed that line and fell into the latter category. While Kanye is widely regarded as the biggest douche the U.S. has to offer, this analysis clearly shows that Jay-Z's self-absorbed qualities are underrated. But before we begin the lyrical breakdown, it is necessary to settle on a definition for douchebag. The word douchebag is, historically, difficult to define. You know if when you see it, but accurately summing it up is a tough task. Given the perplexities of douchedom, we will instead use what I’ll call a “pretension barometer.” It works like this. I’ll cite you a lyric and place it into a culturally relevant, self absorbed context. Still reading? If you are, God bless you. Let’s begin.

The Song: "That's My Bitch"
The Lyric:  How can something so gangsta be so pretty in pictures?
                       Ripped jeans and a blazer and some Louis Vuitton slippers
                       Picasso was alive he woulda made her
                       That’s right nigga Mona Lisa can’t fade her
Courtesy of: Jay-Z
This is the first of Jay's desperate attempts to squeeze in as many sophisticated references into his rhymes as possible. He goes to mausoleums. He cites Socrates and Plato. He needs eight arms to wear watches made by companies that his fanbase has never heard of. But if you’re going to Midnight in Paris-ize your raps, the nods to high culture should at least make sense. Obviously Picasso didn't paint the Mona Lisa, but I'll disregard that. He’s saying beautiful women like this typically exist only in works of art. Jay’s thought process probably went something like this: Who’s a famous painter?  Picasso.  I’ll use that guy’s name. The problem here is that the "bitches" in Picasso’s artwork are painfully ugly. Whether you’re looking at his Blue, his Rose, his African-influenced or his Cubism period (thank you, Wikipedia), the women are almost always deformed. Picasso crafted this beauty in his later days. Would I hit it?  Absolutely. But Jay should be better than that. He does, after all, have five passports.
Pretentious equivalent: In Annie Hall, the Columbia professor who loudly pontificates the meaning of Marshall McLuhan’s work. Unfortunately this time, Picasso isn’t here to tell Jay-Z, “I heard what you were saying. You know nothing of my work.” If life were only like this...

The Song: "Ni**as in Paris"
The Lyric: What's 50 grand to a muhfucka like me?
                       Can you please remind me?
Courtesy of: Jay-Z
This comes off as out of touch with society, but considering the medium, it’s not terribly self-absorbed. 
Pretentious equivalent: Season three of Frazier

The Song: "Gotta Have It"
The Lyric:  Wussup muh'fucka where my money at?
                        You gon make me come down to your house where your mommy at
                        Mummy wrap the kids, have ‘em crying for they mommy back...
                        I wish I could give you this feeling, I’m planking on a million
Courtesy of: Jay-Z
The mummy wrap and planking references are inexcusably lame. But the key issue here is “I care enough about money to chase down some woman and tie up her kids. Yet at the same time, one million dollars means nothing to me.” Can’t have it both ways, Jay.
Pretentious equivalent: Accusing someone of not “getting” a Wes Anderson film, then not being able to explain what it is they don’t “get.” Also, calling movies “films.”

The Song: "Who Gon Stop Me"
The Lyric: I’m riding dirty, trying to get filthy, Pablo Picasso, Rothkos, Rilkes
                      Graduated to the MoMa, and I did all this without a diploma
Courtesy of: Jay-Z
This reads like Jay-Z sent his personal assistant to a museum, had the assistant write down the names of famous artists and desperately tried to work them into his rhymes to show us how cultured he is. And look at him. He did this all without a diploma. If Jay had made it through high school, he might have learned that comparing anything to the Holocaust (as Kanye does in the hook) is a bit of a faux pas. Especially when one of the guys you are referencing, Rothko, was a Jew who was forced to flee his native country because of persecution (thanks again, Wikipedia). Poor form, Jay.
Pretentious equivalent:Dwyane Wade comparing a Miami Heat losing streak to 9/11.

The Song: "Lift Off"
The Lyric:  We gonna take it to the Moon, take it to the stars
                        How many people you know can take it this far?
                        I’m supercharged, we about to take this whole thing to Mars
Courtesy of:Beyonce
Taking it to the Moon is one thing. But stars? You’re talking light years of travel. Be realistic.  Newt Gingrich gets blasted for "grandiose" ideas like these. Jay-Z and Beyonce should be held to a higher standard.
Pretentious equivalent:Gingrich's claim that not only will he serve eight years in the white house, but he will also establish a moon colony there

The Song:"Murder to Excellence"
The Lyric: I dress in Dries and other boutique stores in Paris
                      In sheepskin coats, I silence the lambs...
Courtesy of: Jay-Z
I'm not sure when visiting boutique stores in Paris became acceptable rap fodder, but it's safe to say most of his audience has no idea who Dries Van Noten is. Any reference in a verse to a dry Paris should involve the heiress to the Hilton fortune. And even if that is the direction you want to take it, you would need a time machine to make that joke relevant again.
Pretentious equivalent: Ordering a glass of champagne at a sports bar while all of your friends are drinking beer

The Song: "No Church in the Wild"
The Lyric: Jesus was a carpenter, Yeezy laid beats
                      Hova flow the Holy Ghost
                      Get the hell up out your seats
                      Preach
Courtesy of: Jay-Z
First Jay-Z compares arguably the most narcissistic person in recent history (that we know of) to one of ancient history’s humbler figures. Depending on how religious you are, you might call it ignorant. I’ll call it misguided. He furthers the religious parallel by calling his flow the Holy Ghost. Jay-Z isn't talking about himself as a person. He’s merely talking about his flow. In 2006, Jay dubbed himself the “Mike Jordan of the mic recording.” Five years later, the way he raps makes up one-third of the Holy Trinity. In "Lift Off," Jay says Earth is boring. Clearly he no longer lives there. He tops it off by telling himself to continue to preach.  I think we just found a definition for douchebag.
Culturally pretentious equivalent: There is no equivalent.  A new standard for smug has been set.