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).

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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."

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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.

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).

Style

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!

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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-b***h," 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?!

Stephenie Meyer is the author of the wildly successful Twilight series and Soulja Boy is the creator of the wildly successful "Soulja Boy" song, and you've no doubt seen or heard about these two pop culture phenomenons dozens of times. If you've somehow managed to avoid both of these things, I'm in love with you.

The Pointless, Biographical Similarities

Stephenie Meyer never even wanted to be a writer. She'd never written any stories or treatments or proposals, she was happy being a Mom, and just wrote the Twilight vampire novels for herself, with no intention of ever seeking out a publisher. Her experiment in self-amusement eventually reached a publisher, obviously, who offered her lots and lots of money to write more vampire novels. Soulja Boy, similarly released "Crank That (Soulja Boy)," a catchy(?) hip-hop(?) jam(?), independently on YouTube, without knowing whether or not it would actually do well. It did, and is currently at over one hundred million views, and Twilight has been on the New York Times Best Seller's list more times than I'm comfortable admitting.

Style

Art is subjective, but Soulja Boy is not a very good rapper, and Stephenie Meyer is not a very good author. These two facts, taken alone, aren't that remarkable; there are tons of bad rappers and writers out there, and some of them are even successful, and that's just how life will go until someone figures out how to fix life. What's particularly striking here is that, when Soulja Boy reached a certain level of success, an actually talented rapper (Method Man), came out to ridicule Soulja, saying "I think he sucks, [and is] garbage." Coincidentally, when Meyer reached her level of success, an actually talented writer (Stephen King), came out to ridicule her, saying "Stephenie Meyer can't write worth a darn. She's not very good." Plenty of people are s****y at things, but these are two cases where the shittiness was so profound that established veterans needed to go on record and tell the world that an artist was terrible. Meyer and Boy's badness was actively offensive to other artists.

If this article wasn't already 3,500 words, I would absolutely use this detail for an entry on King/Method similarities.

Both artists represent the absolute worst extreme of their chosen field. They've created something that is successful for reasons that have nothing to do with art; Meyer has learned how to sell sex to teenagers in a way that is comfortable and not scary, and Soulja Boy has learned how to sell ringtones to white people. They're not advancing or challenging their respective genres, they're just cashing in insultingly transparent ways. And their peers hate them for it.

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How about I let the writing speak for itself:

Soulja Boy

"Is 'Soulja Boy' the person, or a dance? Is it a move named after the artist, like 'Do the Bartman'? That would be stupid."

You rhyme "b***h ass" with "b***h ass?" I almost never say this, but Ice T was right -- you should eat a dick.

Well, I can't imagine I've transcribed these lyrics accurately, but I also can't imagine the real lyrics are any less idiotic.

Twilight

What? A character's not allowed to just directly tell the audience 'THIS IS WHO I AM AS A CHARACTER,' right? That's against rules somewhere, right?

There's really just the one "black," there's no need to clarify, it adds absolutely nothing. What are you, some kind of terrible writer?

Oh, I see. Yes.

Anything Else?

I don't like either of these artists. Was that clear?

Now, I won't be sexist and announce that their similarities begin and end at the fact that they were both women. It's ignorant and reductive to claim that these two artists belong to the same class simply because they both have the same basic genital type, so I promise you that there are a bunch of similarities that are unrelated to gender. But, that said, Hey, they were both women! That's one pretty big similarity, right there.

Additionally, both women had strained relationships with their fathers (in a 1997 interview with Vibe magazine, Kim said "me and my father weren't really that close," and according to Wikipedia, Parker "detested her father"). This was tough, because both women were also raised almost exclusively by their fathers because, at age 9, Kim's parents separated and she was stuck with her Dad and Parker's stepmother died, in a weird coincidence, when Parker was nine. When they were both kicked out of their homes (after they'd both faced similarly unsuccessful stints in Catholic school), Parker turned to fiction and poetry, Kim turned to rap. When she got older, Parker was drawn to and struck up several very public relationships with prominent authors, including playwright Charles MacArthur. Her relationship with MacArthur resulted in a pregnancy, which she terminated (quipping, "how like me, putting all of my eggs into one bastard"). Similarly, Kim was drawn to the big names in the rap community, which was evident in her incredibly public affair with Biggie Smalls (and, in a completely tragic coincidence, her relationship also resulted in a pregnancy and eventual abortion, which she described in the song "Hold on").

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You know how the majority of successful comedies over the last few years have been written by, written for, and starring men, until Bridesmaids came out and showed everyone that female-character-driven comedies can be just as successful and hilarious? Dorothy Parker did that first, and harder, and hotter. During a time when the literary landscape was dominated entirely by men, Dorothy Parker emerged out of nowhere with a sharp tongue and a foul mouth and screamed "Women are f*****g funny and amazing and I'm going to f*****g prove it." She became one of the most famous and influential poets and satirists in American literary history, which was amazing. To give you some context, this was the 1920s, when women were mostly quiet housewives; they weren't a huge part of the workforce, there was no "women's lib," or inspirational Rosie the Riveter posters --hell-- America, as a country, was just barely okay with women voting. But Dorothy Parker could not give a s**t. She was going to come out and be vulgar and funny and proud and sexual and political, and she didn't care who knew it. Parker wasn't going to sit idly by while a bunch of men had all the fun. She was going to join in, and do it better.

"Vagina. Deal with it. Deal with this vagina I have."

I'm talking about a woman who burst onto a male-dominated scene and served as an inspiration for all female writers, and if you don't think that's a reasonable lead-in to Lil' Kim, then you weren't paying as much academic attention to mid-nineties hip-hop as I was (what, were you getting laid, or something?). Decades later, when the still-new rap community was almost completely run by and for men, Lil' Kim exploded onto the scene in a way that demanded total attention. She was loud, sexually aggressive to an almost terrifying degree, and could stand toe-to-toe with just about any big male rapper that was on the scene at the same time. There were some women who saw Tupac or Nas and thought "Gee, I'd like to be that famous rap guy's girlfriend." But Lil' Kim looked at these rap giants and said "Pssh. I can do that."

"I also have a vagina, and am slightly less subtle about it."

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Like Dorothy Parker before her, Lil' Kim did not care that her chosen field was a) an established boy's club and b) mostly silent on the subject of female sexuality/empowerment. Kim was not shy about her sexual appetites. It would make sense for me to quote her at this point to illustrate my point, but a lot of her lyrics are honestly too vulgar even for Cracked. If you're curious, just Google "Lil' Kim lyrics." Almost any song that isn't about Biggie or punching Nicki Minaj is about her intimidatingly insatiable sexual appetite. Parker, too, was known for her candid and explicit writing. Parker built her career on "short, viciously humorous poems, many about the perceived ludicrousness of her many (largely unsuccessful) romantic affairs," printed in both Vanity Fair (which eventually fired her for being too controversial), and The New Yorker.

While she published hundreds of poems and short stories, Parker was most famous for her sharp wit (when asked by her editor why she hadn't been turning in her articles, she immediately replied that she was "too f*****g busy, and vice versa"). And whenever Lil' Kim was asked about literally anything, she immediately replied with something clever about f*****g.

And, of course, everyone who wasn't afraid of these women loved them. Lil' Kim released her first album and Dorothy Parker released her first book of poetry, and one was described as "a landmark of bold, hilarious filth" and one was described as "caked with salty humor ... and tarred with a bright, black authenticity." I can't remember which review goes with which artist, but it doesn't matter, because both quotes are equally applicable to both products.

Anything Else?

For some reason, both of these women inspired tribute songs from incredibly unlikely sources. Both Alan Moore (the creator of Watchmen and League of Extraordinary Gentlemen), and Prince, (the creator of all of those Prince songs), wrote tribute songs to Dorothy Parker, despite the fact that neither Prince nor Moore knew Parker personally, and despite the fact that Alan Moore was known for writing crazy awesome comics and not, you know, tribute songs for sassy poets who died when he was 14 years old. And on the Lil' Kim side of things, aging punk rocker/new waver Debbie Harry wrote a tribute song, "Dirty and Deep," when Kim was sent to prison.

"You inspire us."

I have no profound statement to make about this. Just pointing out that two funny, sexually aggressive but chronologically diverse women made a splash in their respective fields, and one of them inspired a song by the guy who made V for Vendetta, and the other inspired a song by the chick from Blondie. And that's weird, to me.

Daniel O'Brien is Cracked's Senior Writer (ladies), and he's way into literature (miserable ghost of Dorothy Parker).

For more on hip-hop and literature, check out The 15 Most Baffling Boasts in the History of Rap and The Gruesome Origins of 5 Popular Fairy Tales.