4 Famous Authors and Their Hip-Hop Equivalents

There's no point to this article. I'm not saying that writers are dead and rappers are running the literary world. I'm not trying to objectively argue that hip-hop is the new, like, "books," or whatever. There's no profound statement, here. Sometimes, if you spend enough time in libraries listening to rap music on your iPod, you notice a bunch of strange similarities, and even though you know these connections are just utterly meaningless coincidences and nothing more; you still want to share them with somebody. But of course there's no grand cosmic reason that several prominent American authors have bizarrely specific parallels in American hip-hop ...

... Unless there totally is!

Ernest Hemingway and Biggie Smalls

If you're serious about building a real familiarity with either American Literature or American Hip-Hop, the quickest way to piss off and alienate yourself from true fans of either world is to say, "Oh, no I still haven't checked out Hemingway (or Biggie)." Art-form-purists will wonder how you can even pretend to be a fan while claiming total ignorance of the big, angry granddaddy of the genre.

And they're right. Ernest Hemingway and Chris "Biggie Smalls" Wallace were really, really good at what they did.

The Pointless Biographical Similarities

For starters, both were incredibly influential in their respective fields (Plus? Fat!), but they also had a bunch of weirdly specific stuff in common. By his close friends, Hemingway was affectionately called "Papa," and according to several reliable sources, Biggie reportedly enjoyed being called "Big Poppa." Hemingway influenced entire generations of writers and Biggie had buttcheeks, wherein techniques reportedly dripped out, directly onto every rapper that came after him. And Hemingway received a Nobel Prize, which I think is the literary equivalent of a Source Award. In 1996, while working on his second album, Biggie was in a terrible car accident that shattered his left leg, and in 1954, Hemingway got into two plane accidents while traveling in Africa.

Biggie discusses suicide often in his music and, by the end of his first album, Ready to Die, he shoots himself (in the song). Hemingway also frequently contemplated suicide and, by the end of his life, he shoots himself (in the face).


Both Biggie and The Notorious Hem.Ing.Way were very blunt and matter-of-fact when it came to their writing styles. Hemingway was never flashy or verbose, like James Joyce; his aim was to be true, and simple. He once said of fellow writer William Faulkner, "Does he really think big emotions come from big words? He thinks I don't know the ten-dollar words. I know them all right. But there are older and simpler and better words, and those are the ones I use." Biggie similarly avoided such flash and ornament in his writing. As Big Daddy Kane says, "[B.I.G.] didn't use a large vocabulary, his wordplay was really simple, he just put his words together a slick way and it worked real good for him."


Both men stuck to writing what they knew (bullfighting, the drug trade, being real great), and saw little value in concocting absurd fantasies. Additionally, Hemingway's protagonists are stoic men exhibiting "grace under pressure," a quality that's very important to Papa, personally and creatively. Likewise, Biggie (operating as his own protagonist), has never been known to crack under pressure -- whether dealing with serious crimes (he keeps his hand steady on his glock) or his treatment of hoes (he does not sweat them), he still boasts a smoothness that stretches all the way back to "the days of Underoos."

Anything Else?

Three of Hemingway's books and two of Biggie's albums (including one double-disc), were released posthumously, meaning these great and influential men had more success dead than most of us will alive.

F. Scott Fitzgerald and Tupac

Want to know what's super-convenient? No one can bring up Biggie without also mention Tupac in a conversation about influential rappers, and no one can bring up Hemingway in a conversation about influential American authors without also talking about Fitzgerald. I mean, it's not super convenient for all of the parties involved (everyone died under pretty horrific circumstances), but for a person like me, whose job it is to find similarities between literature and hip hop, the fact that the Hemingway/Fitzgerald love-hate relationship almost perfectly mirrors the Biggie/Pac love-hate relationship is a real treat. Thanks, universe.

The Pointless Biographical Similarities

Fitzgerald and Hemingway had a relationship that was simultaneously supportive and destructive. They loved and respected each other, but were viciously competitive, because one of them had to be the Greatest Living American Writer of the early-to-mid 20th century, and they both knew it. Someone had to be the voice of their generation, and neither would be content with second place. As is the case with a lot of creative relationships among people in the same field, the lines between admiration and jealousy grew blurry, and what started as a strong friendship between two talented writers evolved into a bitter and depressing feud that was never quite resolved.

Similarly, Biggie and Tupac were wicked tight for a while, and then they (very likely) indirectly caused each other's deaths.

In How to Rap, Bishop Lamont said that Shakur "mastered every element, every aspect" of rapping, which is basically the highest compliment any one person can pay another when it comes to rap. Fitzgerald was paid a similarly high compliment by Don Birnam (of The Lost Weekend), who said of The Great Gatsby, Fitzgerald's masterpiece, "there's no such thing as a flawless novel, but if there is, this is it." And it's not just one fan or one critic showing appreciation; the influence of these two figures reached absolutely everyone that followed. J.D. Salinger often cited Fitzgerald as his chief inspiration, the way that 50 Cent cites Tupac as his inspiration. Also both lived lavish, like players (all day).


As smart and as influential as Tupac was, his flow was never as good as Biggie's (you'll find support of this claim on Yahoo Answers, AllHipHop and your ears if you listen to any Tupac song followed by any Biggie song). The general consensus among critics and fans is that Biggie's technical flow was better than Tupac's, but Shakur's message, passion and ideas eclipsed those of Biggie. Which is sort of perfect when you look at the parallel relationship shared by Hemingway and Fitzgerald; Hemingway was always a more confident and efficient writer, but his work was dwarfed by the passion and drama and excitement that pulsed through Fitzgerald's writing.

I can't even tell which is which!


At a glance, Tupac and Fitzgerald might look like polar opposites, in terms of what they were both rapping/writing about. Tupac was dissatisfied with the lack of equality in America, and his lyrics reflected this sensation. Fitzgerald, on the other hand, wrote about rich white people who really wanted to nail other rich white people.

They seem pretty disparate but, upon closer inspection, their worlds aren't too different. Tupac's lyrics were informed by his life as the child of two prominent members of the Black Panther Party. His parents fought for liberation and equality, and they won, but something was still off, the equality they were promised hadn't come yet. Fitzgerald meanwhile was writing about a similar disillusionment (though his was focused on the American dream, not the belief that he, as an Ivy League-educated white man, was being oppressed in any way). His protagonists were brainwashed into thinking that they could, through hard work and perseverance, "achieve wealth and happiness," and they were always proven wrong. Fitzgerald's Gatsby can amass a fortune and host dozens of lavish parties, but he'll never get what he wants (Daisy), so he'll never truly be happy, because Fitzgerald knew that happiness and the "American Dream" is a lie. Similarly, Tupac was a post-Civil-Rights child who was falsely led to believe that everyone would be treated equally, regardless of their race. They may be writing about completely different societies, but we're still dealing with two writers whose entire careers are born out of the total frustration that comes with discontent and disillusionment.

Anything Else?

Sometimes funerals are perfect. All of Fitzgerald's protagonists are basically Fitzgerald himself (a tall, attractive, wealthy white guy chasing after some crazy broad), so it felt like a really appropriate tribute when, at Fitzgerald's funeral, Dorothy Parker cried out "the poor son-of-a-bitch," a line said at Jay Gatsby's funeral in The Great Gatsby. For an egomaniac like Fitzgerald, having your signature work referenced at your funeral is kind of a perfect send-off. As for Tupac, his body was cremated and some of his ashes were rolled up with some pot and smoked by members of Outlawz. Pac loved the Outlawz and he loved weed and, if he was watching from Rap Heaven, I'm sure he would have loved the whole scene.

Two funeral ceremonies for two cultural giants that were simultaneously really weird and really perfect. Coincidence? Or super-coincidence?!

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Daniel O'Brien

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