Here's How One Writer Spent Way Too Long Deciding the Best Rap Song Every Year from 1979 to 2014

Shea Serrano's new book has a foreword written by Ice-T, so there’s no way the fully-illustrated, 36-chapter year-by-year analysis of rap’s most significant songs will suck.

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Oct 9 2015, 2:00pm

Oh, Shea Serrano. It seems like just yesterday the beloved music writer was an 8th grade science teacher, moonlighting some of his first writing gigs for Noisey and dropping sage hip-hop knowledge and witticisms in pieces like his review of a middle school talent show and that profile on Houston rapper Maxo Kream. Well, Shea's all grown up now, having found his way to a staff writer gig at Grantland. He's even got a couple books to his name now. If you consider a "coloring and activity book" a real book, pssshhh. (Just kidding, we think it's awesome.)

Serrano's latest, The Rap Year Book: The Most Important Song From Every Year Since 1979, Discussed, Debated, and Reconstructed, hasn’t even come out yet—it drops October 13—and it’s already the number one best-selling book in three of Amazon’s categories (rap, history and criticism, and popular humor and entertainment). The publishers have even already ordered a second printing of it. We’re so proud!

And anyway, with a foreword written by Ice-T, there’s no way the fully-illustrated, 36-chapter year-by-year analysis of rap’s most important songs will suck. Of course, you might disagree with some of Serrano's choices—was “Still Tippin’” really more important than “Drop It Like It’s Hot” in 2004?—but that’s life, bro.

Given our excitement for what just might be one of the most important rap tomes in the history of rap tomes, we gave Serrano a call at his home in Houston to find out more about the book, blowing his deadline, and predicting Kanye’s bid for presidency.

Continued below.

Noisey: Hey Shea. First off, I wanna say you're awesome. I read your Twitter feed daily and it always makes me laugh.
Shea Serrano:
Well, that’s good. I feel like you're right in all of the things you're saying so far. It's all correct.

In terms of music, are you listening to anything right now that you're really into?
SS:
You know, when you called, I was listening to Kendrick's tape, To Pimp A Butterfly. I listen to that all the time. But new guys, there's this guy named Cousin Stizz that somebody told me about. I don't remember where I heard about him. He's got a really good tape that I'm just very, very into. So I've only been listening to him and the Kendrick tape and then, you know, whatever one-off songs come on the internet.

Let's talk about your books. Starting with Bun B's Rapper Coloring and Activity Book from 2013. How'd you come up with the idea for that one?
SS:
I'd met Bun B a couple times and I guess he knew who I was. So we talked about doing a book together and we were just bouncing ideas back and forth. Originally, it was supposed to be like some “survival guide to rap”-type thing, but we could never get it to fit right. So we were just looking for ideas and one day I was drawing pictures of local rappers in Houston and posting them on Twitter. I was with my kids and they were drawing and I was drawing. Whatever. So, I posted them on there and the people who knew the guys were really excited about them. So I thought, “Maybe if we do the real famous rappers then more people will be excited.” I messaged Bun and asked him, “What do you think about doing a coloring book with these guys?” I thought he was going to say “no” because he's a rapper and, you know, but he was into it. So I downloaded the trial version of Adobe Illustrator for thirty bucks and figured it out. I drew a couple pages and I sent it to him and he was like, “Let’s fucking do it.” So I put them on Tumblr and then a week later, I had maybe five or six pages up there, and I got a call from a book editor. It went viral so she had seen it. It all happened like boom, boom, boom once we started it.

Who’s been the hardest rapper to draw?
SS:
Ugh. Big Boi, surprisingly. Just because his face is non-descript, I guess. He doesn’t have, like, a cool scar going down the middle of it or facial hair or anything like that. It's just a normal looking face. So you draw it and you're like, “Does this look like Big Boi? I don’t know if it looks like him or not.” He's not a guy that's real easy to tell.

I get that. Let's talk about the Rap Year Book. How did the idea for that come about?
SS:
The idea for that came about from my editor for the coloring book and she was like, “Let's do another book.” I was like, “Alright, we'll do another book. But I don’t want to do a coloring book because it was a big hassle.” Everybody that was in the coloring book had to sign a paper saying that they would be in there. That part itself took at least six months and it was the biggest fucking headache.

We were going back and forth about what to do and she told me the idea for the rap year book. It didn’t have a title back then, but she explained it like, “You write one chapter for the most important song of each year. You just pick one and explain why.” I said, “Look, no, I don’t want to do that. That sounds awful. I don’t want to research this thing. I don’t care about rap music from 1982. It's not a part of my life. I'm not interested in it.” So we just went on, doing whatever, and then my wife was like, “Oh, we've got to move houses.” We were in a townhouse and we had two kids at the time, then we had a third. So, we needed money for a down payment for a real house. And I was like, “Well, I guess I'm doing the rap year book now.”

It wasn’t until I worked on it maybe seven or eight months down the road that it sort of started to take shape and I realized this is going to be a really cool thing if I can fit all the pieces together right.

Wow. So you probably had to do a lot of research for the book, especially since you said you're not that into older or early rap, right?
SS:
It was the worst thing. It was so bad. It was like going back to college. Because you have this cursory understanding of something, you know some names, “Oh Kurtis blow, yeah, yeah,” but I didn’t know the people involved or the events that were happening around that time that caused rap to become a thing. It took a long time.

Where did you do your research? Was the library any help?
SS:
That's the crazy thing. You can go to [University of Texas] and they have a whole bunch of old magazines, like an archive basically. So, I was searching through like old Vibe issues from 1991 and looking for the guy I was writing about. There are also different services on the internet that you can pay for that archive all the old news stories and you can go and read stuff through that. I did that and I read a bunch of old books. I talked to a bunch of people and, you know, some guys were really helpful. I always mention Chuck Eddy, who was a big time rap writer in the 80s. He was covering all of that stuff. And Brandon Soderberg. He's sort of been around writing for awhile and he's a super smart guy. There are writers in different places who have expertise in different things and they're always excited to talk about that thing because they know so much about it. I was really leaning on a lot of people to put this thing together.

From the inception of the book—or the moment you decided to buy a house—to turning it in to your editor, how long did the whole project take?
SS:
Let me tell you what happened, because this is the dumbest thing and I'm embarrassed that it happened this way. They gave me a year to write the book and I said, “Alright, cool.” I thought, “There’s no way I'm going to need a year to write 36 essays. I can write an essay in two hours,” This is what I’m thinking in my head. So I waited like eight months, maybe nine months and I hadn’t done a single thing on the book. I’m like, I'm just gonna crank it out. It's not gonna be a problem. And then I got to ten months, 11 months, and I still hadn’t started anything. Then I started getting emails from my editor, like, “Yo, what’s going on? Where's my stuff?” So I'm like, “Alright, let me go ahead and get started.” There was like six weeks left before all the chapters were due and I had done two chapters and there's 36 of them in the book. So I was in panic mode. I sat down to do the DMX chapter [1998: “Ruff Ryder’s Anthem”], and I started to write it. I knew a little bit about DMX. I had read his autobiography, but I didn’t know enough, so I had to research a whole bunch of other junk to put in the pieces around it. It took me a week to do that one chapter. Every single night, like eight hours a night, I would work on it. Oh, my god. So I knew right then I wasn’t going to finish in time.

The day comes for me to turn in all the chapters and I have eight of them done and she was not happy about that. They gave me an extra couple months to finish the thing. It was around that time when I really was getting after it when I said, “OK, this is what I want each one to look like.” Because that was the hardest thing: figuring out the template. How do I make this easiest to read? How do I make it enjoyable? Some of that stuff is heavy information. It wasn't fun until it was all done and I saw it and was like, “Oh, my god, this is incredible.”

Are you worried about people’s reactions to your song choices?
SS:
No, that's the last thing I'm worried about.

What are you worried about?
SS:
Well, there are a handful of people who I really look up to as writers or editors and think are very talented, so those are the people who I care what they say. But, as far as people on Twitter or whatever, it's gonna be what it always is. You write something and a group of people tell you how great it is and a group of people tell you how terrible it is. But the point of the book is to start a conversation. There's no way you put together something like that and everybody goes, “Well, he got this exactly right.”

We put up the 2004 chapter on Grantland, and I laid it all out as clear as I could lay it out. In the first section, it says, “This is not the best song of 2004. The best and most important are two different things. Kanye West's ‘Jesus Walks’ was the best song of 2004. But this song was more important. Here's why.” And then on Twitter all day people were saying stuff like, “I can’t believe that you said this song was better than ‘Jesus Walks.’” Are you fucking kidding me, guys? You're not looking at anything. So that happens with stuff, but that's what I want to happen. That's the fun part of it. I want to have that conversation. I want to explain why Macklemore “Same Love” was very important to music, even if you hated it. Some of the stuff is impossible to ignore and some of it will be inarguable. There was no song more important than “Nuthin But a ‘G’ Thang,” but with some of them, there are gonna be some spaces. Like, "1994 [should be] a Biggie song instead of a Nas song," and I'm already hearing about that. It's just how it works, man.

Do you have a number one most important song out of all the years in your mind?
SS:
Out of all the years, the most important...you know, I might pick “Nuthin But a ‘G’ Thang,” possibly because I was just listening to it this morning. But Dr. Dre, you know, his reach is just all over everything for so many years, so I might just start with him because it seems like the easiest one.

Do you think the book will appeal to people who don’t even like rap?
SS: Yeah, it definitely will. A bunch of the book isn’t even about rap. That's a secret. Because I didn’t want 2,000 straight words explaining why a song was the most important song. Because then you have to read that 36 times and it becomes super boring. So every chapter, rather than it just being straight text, is broken up into different sections. And some of the parts are not about rap. Like in the 2004 chapter, there's a whole section about Mean Girls because it came out that year. And then, in the Public Enemy chapter, there's a whole section about the time I got into a fistfight. There's more important stuff than just the rap stuff, but that other stuff is tied to that rap song so that's why it's important.

I saw that you predicted Kanye's bid to run for president in an “alternate reality chart” in the book. Are you clairvoyant?
SS:
I didn’t even realize I'd done that until we sent out advanced copies of the book and one of the media guys messaged me. He was like, “Yo, did you realize you did this?” And I didn’t. I had completely forgot about it. I was so close. I predicted 2016 and he did 2020. If I had been thinking about it I would have put 2020, but...

You like to give away little gift thingies to people on Twitter, or now to people who are going to be attending your book events, like the DJ Screw bookmark or those Gucci Mane T-shirts. I feel like the sentiment behind those giveaways is that deep down inside we're all kids who love free shit and goodies.
SS:
Yeah, I mean, I just like to do stuff like that. Before I was a writer I was a teacher and I figured out real early on that if you just show even a little bit of extra attention to something, kids will get really excited. It doesn’t even have to be anything special. I'll give you an example. I wear glasses, right? And in one of my classes there were like six other kids who were wearing glasses, so I was like, “Oh man, check this out. Me, you, and all these other kids with glasses, that's a new gang. We're the glasses gang.” And I wrote it on the board and I put down their names and I gave them like a little sticker type thing and they were really excited about it. It became this whole thing where the next year I got kids in my class who were like, “Oh, am I in the glasses gang?” They were excited about it, you know? Little stuff like that people get really into.

So I decided to try that with the book. Do something a little bit extra. I bought a box of Yo! MTV Raps cards and I was like, “Yo, I'm at the post office. The first 30-whatever people to send me a picture showing me they bought the book, I going to mail you a pack.” And then boom, they went crazy for it. So I was like, “Well, I guess I’m gonna do this a lot.” So that's how all that started. Like how do you get somebody excited about a book, you know? And this was before anybody had seen the book. Yesterday was the first time anybody saw it. So up until that point they weren’t really buying the book, they were buying whether or not they liked me.

That's pretty cool. So what's next for you in terms of books? Are you going to work on something again in the future or next time you need money?
SS:
Haha. We already did a third book deal. We've got that done and taken care of. I don’t know what happens beyond that. I really like writing and I like the people that I'm working with. I couldn’t tell you exactly what comes later on, but I know we're doing another book and after that who knows? Maybe everybody will realize I’m not very talented and then I won't get anymore work and...

...You'll go back to teaching?
SS:
Yeah, back to teaching. Teaching is great. I'm gonna go back there anyways.

Lastly, who's the guy that you use in your Twitter profile image?
SS:
You don't know who that is? I'm so glad you're just telling me this now because I would have hung up the phone on you and never talked to you again. That guy is Miklo Velka and he is a character from a movie called Blood In, Blood Out, which is about three family members who are Mexican in Los Angeles in the 70s. It's my favorite movie and he's my favorite character. So there you go. People ask me that all the time and it blows my mind that they don't know who he is.

Well, can I use the excuse that I'm not Mexican to explain why I don't know?
SS:
No! You know who Martin Luther King is. And Martin Luther King is less important than Miklo Velka.

Shea Serrano’s The Rap Year Book: The Most Important Rap Song From Every Year Since 1979, Discussed, Debated, and Reconstructed comes out October 13 via Abrams Image. Preorder it on Amazon and follow Shea Serrano on Twitter.

Jessie Schiewe writes the bulk of her articles with her chihuahua, Mischa, on her lap. Follow her Twitter.