People With Passion: David Drake, music writer

A People with Passion series

Chicago journalism

January 18, 2012: David Drake

David Drake, during his DJ days.

We are meeting at Filter Coffee Shop on Milwaukee Ave. in the late afternoon. David is quiet yet loquacious, with a deep knowledge and passion for music, particularly hip-hop. It is that passion for the music mixed with a love of writing, an authority of opinion, and relentless networking that has allowed him to leave his day job and make, as he puts it, ‘a run’ at writing.

Here, in the 23rd installment of my Chicago journalism interview series, David Drake of Pitchfork, Fader, the Tribune, and his blog discusses his life as a working freelance writer, and describes the process of how he created the connections required for such a career.

I’m thinking now backwards, because I’ve never really thought consciously about making those connections. This is something that just took a while but eventually it happened. I think there’s a couple of advantages I have. Number one, I’m writing about rap music, which is in critical terms very poorly covered. I think a very narrow slice of what hip-hop is currently being made is actually being covered by magazines. If you have any kind of knowledge whatsoever, if you take your time trying to understand the actual scope, then you immediately stand out.

I feel like for a long time I had all of these ideas about this stuff like, “I can’t believe these guys aren’t that good at this. They’re not covering this the way they should be.” But I could only make my impact felt once in a while because I had a day job. It kept me from writing regularly, and that really was the biggest key for me.

In 2008, Gucci Mane was the hottest rising street rapper, and my friend who teaches in the high schools on the southside was talking about how all of her students were like, “Gucci Mane’s better than Jeezy.” I was listening to these tapes, and I was like, “These are amazing.” There was literally zero internet notice beyond facebook comments and youtube comments about it.

Funny, that’s where I heard also, was from my students.

Yeah, they know man. Pulse of the detention hall. (Laughs.) And basically my friend and I were like, “Okay, we’re going to listen to all of these tracks, and we’ll just make a list of them.” We came up with 30 tracks that we thought were his best ones from the year, and we posted them on this site. I’d done this hip-hop blog on and off, fairly regularly since about 2004, We posted these 30 songs, and we wrote 30 blurbs to go with them. And it got linked all over the place.

When Vibe Magazine wrote their first piece on Gucci’s reemergence in 2008, they emailed me to get quotes for it, because I was basically the first critic, internet-level person to write seriously about his new stuff when he had his comeback thing. And it became this big thing. I posted on that site maybe five times the entire year, and that was one of them, and Vibe ended up listing us as one of the 50 best rap blogs, which is hilarious because we barely ever updated. (Laughs.) But it was solely off of that.

I felt like I had something to contribute. I felt like I was just paying better attention to rap music than a lot of critics that write about it. They’re paying attention to what other critics are talking about. It’s a very myopic world.

I just tried to write about stuff that in some way felt unique or necessary or important in some way. The fact that I think that hip-hop is so poorly covered makes it a lot easier for me to stand out, because a lot of times people treat it like it’s not possible for them to understand it. They think, like, that they don’t have the ‘authority’ to write about it. And that’s a mistake. That’s almost like other-izing people because you’re not black or you’re not young or you’re not whatever. You might think that what you’re doing is respectful, “Oh, I can’t comment on your…” Really what you’re doing is treating them as if they’re different, as if someone else doesn’t have the same emotions and feelings that you might have when you listen to it.

Right after that was when I started writing for Pitchfork. I’d been bothering Scott Plagenhoef, who is the former editor-in-chief there. I just kept emailing him for a while, like, “You guys aren’t covering hip-hop well. Let me do it.” and I just kept emailing him, and at some point I guess he just relented.

How often would you email him?

I think I’d emailed him three or four times.

So this wasn’t like Shawshank, writing the warden once a week or whatever.

No, no, (laughs), It wasn’t quite that bad. But I had to follow up and everything. And I knew he was listening to me, too, because I’d run into him at Sonotheque. He was DJing with Mark Richardson, who has a Pitchfork DJ thing there. He was like, “What have you been listening to lately?” And I told him – it was a Statik Selektah CD or something, and a month or two later, Tom Breihan wrote a review of the CD, and he didn’t like it. (Laughs.) He gave it a negative review. And I was like, “Oh, this guy is listening to what I said. They’re actually covering it.” So I figured that he must be listening to me to some degree.

Eventually he had me do a trial – they have you do a review or two and see how it works out, and eventually I got on. This would have been right in the wake of that being covered all over the place, so maybe that sort of tipped him over the edge. I think that was one of the immediate results of that piece.

But it wasn’t just that piece. Eventually you sort of – I just covered King Louie, the big rising rapper in Chicago, and I got an interview with him because Drew Barber from Fake Shore Drive, I forget when exactly it was, but he said the reason he started reading my site was because Noz who does the website Cocaine Blunts had linked to me at one point, and he trusted Noz. Noz was also one of the people who linked to my Gucci piece. So a lot of times those connections you don’t even realize.

I feel like the reason that anyone has given me the jobs that I’ve had, it’s either been through persistence or through creating a unique – it sounds so horribly commercial – but creating a unique product. And that really is what you’re doing. You’re just covering a story that other people aren’t. Eventually, it got to a point where once I got the Tribune job and the Pitchfork thing, I felt like I wanted to see if I could do (pause) I felt like the connections were there at that point, that what my biggest failing so far was consistency.

Consistency in your output?

Yeah, exactly. Pitchfork, I was doing about once a month. That didn’t feel like enough. I would spend a lot of time keeping up with music and talking about it with friends online and chatting about stuff. I would blog occasionally, but it wasn’t like long pieces or anything like that.

The other thing that happened was that for a long time I wanted to DJ too. And I’d been DJing around town, but those gigs, you have to be really persistent. And it became sort of prohibitively expensive, because I was collecting records to do it. I didn’t have Serato, which is like the standard, so I was like, “Well, I might as well go into writing more and focus on that instead.”

I basically was trying to move into that direction anyways, and also getting into my late 20s and I was like desperate to do something with my life, I guess. When that King Louie story happened, I blogged for about two months. Fader picked me up right after that, and I just forced myself to do at least four pieces per week on my blog, and at least have a paragraph of text with it.

The thing with King Louie was that he was basically an unknown quantity outside of the southside of Chicago. He was buzzing huge down there. He had youtubes with 150,000 views, but no national coverage whatsoever. That’s something that’s finally changing now, and is really exciting to me. These guys can now bypass the music industry totally and say, “100,000 people listened to this” and Vibe Magazine is still covering this guy who has like 10,000 views, but he’s from New York. (Laughs.)

Well does it worry you at all that in the process of them bypassing the greater industry that they could possibly bypass the music press?

I think that’s one of the fun things about music writing right now and the internet, is that you sort of – maybe this is how I should have answered that question earlier too. You create your own identity as a writer. If people can associate me with my name as a byline, then I don’t have to tie myself to any artist. I tie myself to good music. And if people trust my taste in music and what I’m writing about and they trust me to write about it in a way that’s honest, then – I mean, the fact is that at some point it’s got to be covered, because people pay attention to coverage. That’s how they filter. There’s so much content out there and they need someone to filter it. And that’s what my job becomes at some level.

One of the exciting things – they do bypass the press, and that actually makes my job even easier, because then I can go in and find a video with 100,000 views and be like, “You guys are all missing this.” And suddenly, once again, I can write a piece and everyone’s gonna be like, “Oh.” When the music industry doesn’t have a stranglehold, then access is no longer the primary, like – XXL or Vibe don’t have the sole rights to interviewing these major artists, so I can go out and interview King Louie and I don’t need to have a Vibe because Vibe isn’t even up on him yet, or XXL isn’t up on him yet.

Well, that’s interesting – do you use youtube to figure out subjects that you want to cover?

That’s one of the ways, because everybody uses youtube. It’s a very sort of universal distribution. And there aren’t too many things like that right now. For a while there were some other ones too – I think it was called Imeen, and when the Gucci thing was happening, that was really big.

Chief Keef is somebody I just wrote about for Fader. He’s a Chicago rapper who’s 16. His youtube for the song “Bang” just crossed 500,000 views. 500,000. No media coverage. The closest he got to media coverage – he was in jail for a couple months, and when he was getting out, there was this fan of his on the southside, some 12, 13-year-old, and when he found out he flips out and his brother or parent or someone video tapes this kid like, “Yeah! Chief Keef’s free!” Like freaking out.

They posted it on World Star Hip Hop, and all of a sudden, Chief Keef’s “Bang” video goes from 400,000 to 450,000, and suddenly there’s all this traffic, with people like, “Who the hell is…” because no one in the rest of the country outside of the southside knows Chief Keef. But in the southside of Chicago, he’s a superstar. And you could say it was the World Star thing, but he already had 400,000 views before World Star even happened. He was playing shows. There’s a video on youtube of him playing a show at Adrianna’s on the southside, like and all these kids are out there yelling all of the words back at him. He’s like a superstar. And has no coverage in the press.

Do you think that newspapers and more established media outlets are going to have to change the way they cover music? Is there a threat that THEY could get left behind, or do they just live on their name and eventually they pull it together…

I think the only people who are going to be left behind are music journalists who don’t do a good job of covering music. I kind of like this time, because it’s more competitive, and it sort of keeps you on your toes to do a better – really, all a newspaper is is a way of funding and the name. It’s a brand name. But it seems to me that who’s getting more power right now is individual writers. I can have my own website, and I can do all of my journalism on my own website, and suddenly it becomes more valuable. Now, I can’t afford to do that (laughs) but it gives individual writers a lot more power. Individual writers become the brands themselves in a way that they couldn’t back when you had to be published in a newspaper for anyone to even know who you were.

The thing about freelancing is that there are so many skills you have to have, some of them I’m pretty good at. I’m pretty good at the networking thing, and creating a need for my services in the industry. Not so good at managing finances. Something I’ve been working at of late.

What are the other skills needed to be a freelancer?

One of the biggest things that I’ve been working on too that I’m not great at yet is pitching for your publication. I think the hardest thing is you have a lot of ideas about stuff that would be good to write about, and when you’re doing your own site, it’s easy, because you can just publish them. (Laughs.) But then you realize that a lot of times with editors at different publications, they’re like, “Alright, but what’s the local angle on this?” Or, “Okay, but what’s the news peg here?” Thinking like an editor is very different than thinking like a writer. You’re like, “But these are ideas that need to be said.” And then they’re like, “Yeah, but why is anyone going to read this?”

So coming up with pitches for the right people and being able to juggle those pitches and move them onto the next editor when the first one declines, and then following up when they don’t answer you – that stuff is the hardest about being freelance. That’s my least favorite part. The money part you can work on. You can get better at keeping track and then shaking people down for money, but getting your pieces placed… (Pause)

Part of me sort of suspects that I’m working to get out of freelancing. A lot of the decisions that I make are less driven by getting money and more driven by making my impact. Keeping my “brand,” air quotes, intact. Focusing in on the kind of stuff that people are actually going to want – I’m thinking long-term about my career rather than short-term about paying the rent this month, which is not always good, but I think hopefully it will lead to something some day.

I can’t imagine myself, especially in this day and age, writing for the short-term check. You’re really writing for your legacy, because eventually hopefully someone reads that legacy and is like – I mean, this is just my hope – but then they’re like, “You should have a full-time job! (Laughs.) Here are some benefits.” I feel like at some point it’s gotta come back around to that if you do your work well enough, if you do a good enough job, someone’s going to see you as a bigger asset on staff full-time. That’s my hope anyway.

Jack M Silverstein is an oral historian working in Chicago. His non-fiction novella Our President about Barack Obama’s inauguration is available at Amazon. Say hey on Twitter @ReadJack.

Check back every Wednesday at Eye on Chi for more of Jack M Silverstein’s People with Passion interviews with Chicago journalists. Coming next Wednesday, February 22: Jim DeRogatis, Sound Opinions/WBEZ.


(NOTE: The dates below refer to the date of the interview. The order is the date they were run.)

December 29, 2011: Tran Ha, RedEye (EXCERPT, FULL)

December 24, 2011: Sam Smith, (EXCERPTS, PART IPART IIPART III)

December 20, 2011: Ben Joravsky, Chicago Reader (EXCERPTFULL)

December 9, 2011: Chuck Swirsky, Chicago Bulls play-by-play announcer (EXCERPTFULL)

December 14, 2011: Sarah Spain, ESPN personality (EXCERPTFULL)

December 6, 2011: Jon Greenberg, ESPN Chicago, columnist  (EXCERPTFULL)

October 21, 2011: William Lee, Chicago Tribune breaking news reporter (EXCERPTFULL)

November 4, 2011: Elaine Coorens, Our Urban Times founder (EXCERPTFULL)

November 4, 2011: Andrew Barber, Fake Shore Drive founder (EXCERPTFULL)

October 21, 2011: Jane Hirt, Chicago Tribune, managing editor (EXCERPTFULL)

September 19, 2011: Andrew Huff, Gapers Block founder (EXCERPTFULL)

September 21, 2011: Chris Cascarano, Chicago News Cooperative, video producer (EXCERPTFULL)

September 30, 2011: Christie Hefner, Playboy, former CEO  (EXCERPTFULL)

September 15, 2011: Alden Loury, Chicago Reporter, publisher  (EXCERPTFULL)

August 17, 2011: Steve Chapman, Chicago Tribune, editorial board and columnist  (EXCERPTFULL)

September 13, 2011: Kimbriell Kelly, Chicago Reporter, editor  (EXCERPTFULL)

August 26, 2011: Chuck Sudo, Chicagoist, editor  (EXCERPTFULL)

August 17, 2011: Clayton Hauck, photographer  (EXCERPTFULL)

August 18, 2011: Rick Telander, Chicago (EXCERPTFULL)

August 15, 2011: Mick Dumke, Chicago Reader, investigative reporter  (EXCERPTFULL)

December 12, 2008: Alex Kotlowitz (re-edited August 15, 2011)

August 10, 2011: Mary Schmich, Chicago Tribune, columnist  (EXCERPTFULL)

August 4, 2011: Rick Kogan, Chicago Tribune, columnist  (EXCERPTFULL)


4 Replies to “People With Passion: David Drake, music writer”

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