Shawn Gee: Most of the artist websites that were up on the net at the time were really just digital posters for lack of a better term. You saw the homepage, you saw the tour page, you saw some advertisements for records, and you may have been able to click on some photos from back in the day, but after you went once, there was really no reason to go back. One of the things we wanted to do was build something dynamic, that would change, that would give Roots fans a reason to continually visit the site.

Questlove: One day after a concert, Angela was talking about the Internet. I said I got a computer. She’s like, “Well, what is it?” I said I had Web TV. She said that wasn’t a real computer. I said it was. We argued back and forth and finally I took her to the bedroom to show her my set-up. In my head I thought I was Matthew Broderick in War Games. I was that guy. I was into ghetto shit. I’m thinking I’m Dr. Futuristic with my drum machines and turntables.

She gave me that look. It was that look like I forgot to take out the garbage and my mom and dad would wake me up Friday morning—you know, if you walk by them you would get a smack in the head. She was like, “Oh hell no, I can’t.” I was like, “What are you talking about?” She said, “I can’t watch another person fall victim to this... Look, I just want you to trust me.”


One of the things we wanted to do was build something dynamic, that would change, that would give Roots fans a reason to continually visit the site. —Shawn Gee


I happened to tell her that I was going to invest in getting a Pathfinder. She knew I didn’t have a license. She just didn’t like where she saw my life going. She’s like, “Look, it’s asinine for you to buy a car without a license. Either you’re going to get your license or don’t get a car. But please don’t get a car and be one of these dumb rapper motherfuckers getting your boy to drive you around.”

She’s like, “Why don’t you take that money and invest in your future?” I was like, “Huh?” She was like, “Take that $15,000 you going to take to buy the car and invest in your future.” She hammered it home for like 25 minutes. Next thing I know, I’m in CompUSA with her and two of her friends from the University of Pennsylvania. She tells them, “Get me your wet dream.” She told them to buy what they wish they had. I still didn’t know what she was doing. She’s like, “I’m building you your website,” and for the next three months, my bedroom became Ivy League school central.

I didn’t even know black nerds were real. She just had them in rotation—Urkel is a dweeb, but I was like, “Wow! Brothers really can be cool and educated. How come I’ve never seen this stereotype?” It transformed me.

Shawn Gee: The site had to have a personality; it had to have a voice. A lot of the time, if you’re going to a web company that built 15 other artist’s sites, they’re usually working from a template. There’s no voice, there’s no personality. So Ahmir had a friendship with a young lady who went the Univeristy of Penn who wasn’t in the digital business—but she was a web head. She understood the dynamic of the web, she understood the community aspect. She belonged to a lot of the early digital communities. And she was a geek as well. And she was a music head. And she was a Roots fan. So it was like 1 + 1 + 1 = 1000 with her.

We had a meeting with Ang and explained to her what we were interested in doing. Instead of just hiring her to build the site, we spoke about bringing her on The Roots payroll to work in a salaried position as a web designer and host—a web mistress, I think she called it. And that was probably the first great decision made in the history of the Okayplayer, because Ang was able to give Okayplayer that personality and that voice

Questlove: My house was always a haven. It was constantly being occupied by somewhere between 10 to 15 people. We were sort of like the East Coast version of The Pharcyde Manor. First floor was where all the writers and singers were. Any lyrical ideas that had to get done, that’s where that happened. The second floor—that’s where all the tech nerds hung.

Angela asked me what I wanted from the site and I told her I wanted to build a playground where people can actually interact with me. At the point, I told her I’ll be online four hours a day. She thought that was ridiculous. She’s like, “No one is on four hours a day.” I said, “I’ll bet you I’ll be online four hours a day.” When the site first came up, I was on it six hours a day.

Shawn Gee: For the first two or three months the website was run out of Quest’s bedroom. Ang asked for a bunch of materials, we got a bunch of pictures and different things. The guys were going on a four-to-five-month tour right after Angie was hired. So we set the computer up in Ahmir’s bedroom. Ahmir gave her the keys.

Questlove’s bedroom was like a storage place with any asset you would want. Whether that was old VHS of The Roots performing or photo shoots or whatever Roots paraphernalia—it was somewhere in that bedroom. So Ang spent a lot of time going through those things and found enough assets to put together what was initially a splash page that had the graphics and images from the Things Fall Apart album.

Questlove: Slowly but surely, as I would leave the house to go to the studio to record, she would come to the house and build Okayplayer. I would like to think we finished both projects at the same time. I mastered that record [Things Fall Apart] in November of 1998 for release in February. I believe we actually went live a week and a half after the album came out. We haven’t turned back since.

Shawn Gee: When the guys were over in Europe, Ahmir would call back and give Ang updates on each show and what they were doing. Ang would type the update in real time so when someone woke up the next morning and went to they had new information.

In these days and times a blog seems like a simple concept, but you gotta figure this is 13 years ago, where there were no blogs. It was all sort of static advertisements. That’s all websites were. It was a novel concept to have dynamic information that changed not only once a day but multiple times within a day.

Talib Kweli: In ‘99 when the site went live it was like this crazy idea. Okayplayer was the first tastemaker website. There was no Complex or Nahright or Pitchfork. It was like the first for us—the first prominent tastemaker site for hip-hop.

Questlove: Angela pretty much wrote all the updates. That’s where the real charm of Okayplayer came in. Angie was defying all stereotypes. She was a beautiful girl who had a crazy sense of humor. Even more than me, she was the one who connected with the initial class of ’99—the people who first started coming into the boards. She became the voice. She had a lively style.

Dan Petruzzi: Angela’s from deep southwest Philadelphia, one of the more dangerous parts of Philly. She was curly haired, super intelligent, and really, really funny—that was her most noticeable asset. Okayplayer was built on comedy—the blogging early on, was built on comedy and practical jokes and she was great for that. And you know, I don’t know how she met Ahmir, but she had a blog called “The Broke Diaries,” that was hosted at the University of Pennsylvania, and it got some attention because the writing was really good and the stories were hilarious.

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