OkayAlumni: Rob Cave – Okayplayer

February 21, 2025 1

“It was school for me. My professors were Shawn Gee, Angela Nissel, Questlove, Donwill.”

This is how Rob Cave Jr., one of the first Okayplayers, as well as a graphic designer and rapper, summed up his time having an integral hand in the world of OKP throughout the late ‘90s and early ‘00s.

Growing up in Brooklyn, he’d ultimately make his way to Philadelphia after getting accepted to the now-defunct Art Institute of Philadelphia. But it’d be his time working at the Okayplayer offices there — first as an intern with daily duties encompassing ordering sandwiches, helping build the OKP website, designing tour merch and many, many, many other responsibilities, before being brought on full-time — where he’d get a hands-on learning experience unlike any other.

It was appearing at a video shoot for Dead Prez’s “Hip Hop” at the Masonic Temple in Brooklyn — and then a Black Lily event later that day in Manhattan hosted by The Roots — that led to Cave learning about Okayplayer and ultimately working for it. His time there would put him on game to how the music and entertainment industries work. But also as a supporter, it allowed him to interact with artists he was (or would become) fans of. He’d get an early look at D’Angelo’s “Untitled (How Does It Feel)” music video, as well as work on websites for other artists like Talib Kweli and Dilated Peoples.

He’d even have a slightly awkward encounter with a then-up-and-coming Jill Scott, who he was unaware was already familiar with The Roots crew when he didn’t let her in the side door of a venue prior to a Black Lily event. (He didn’t want to upset late Roots manager Rich Nichols who, earlier that day, had claimed that the street team Cave was a part of was letting people in without paying, telling Cave’s boss, “Your [team is] letting in all these motherf**kers in here for free?”

“Later on that night, The Roots are on stage like, ‘Make some noise for my girl from Philly, Jill Scott.’ And she tore the shit down. I’m standing there with my f**king face on the floor, like, ‘Oh my God, I slammed the door in this girl’s face,’” Cave recalled.

His time with Okayplayer also led to longtime friendships courtesy of OKP’s message boards, where he’d meet Von Pea of Tanya Morgan and Che Grand. This also culminated in the creation of The Lessondary, a collective named after “The Lesson,” a subforum on the message boards, that includes Cave, Von Pea, Che Grand, Donwill and Elucid.

As Cave shared, this experience came at a much-needed time. He met most of the Okayplayer team back then shortly after his dad died (his mother had also passed a few years prior), and their support and guidance set him — a then-high school senior about to embark on college — straight.

Fast-forward to now, and he’s done design work for the NBA, Def Jam, Christina Milian, and he recently released a new album, Kairos.

In honor of Okayplayer turning 26, Cave spoke with us about how he came to learn of Okayplayer, his time with OKP and how it impacted his life, some of his fondest memories from working with OKP, and more — including how he indirectly coined another name for Okayplayer’s website that only real heads know: “That Site.”

Shared in as-told-to format, lightly edited for length and clarity, here’s Cave.

Rob Cave: [Angela Nissel] was the webmaster; she would give me my task list for the week, pretty much. And it was a lot of that. I think the first featured artist [I built a website for] might have been Talib Kweli for the Reflection Eternal album. That was the first thing I did completely on my own. Before that, Doug [Muir] did most of the sites, and I did most of the maintenance on the sites.

When I did the Reflection Eternal site, Kweli came into the office to check it out, and when I showed him something, he did not know how to use a computer. He kind of poked the mouse like it was going to do something. He moved the mouse with one finger, and I was like, ‘No, you got to hold it, and move it around.’ It was funny.

My favorite thing probably has to be the Dilated Peoples website we did. It was like a game. You had to find a token, and then get into a train station and find s**t. It was very, very interactive. It was in the heyday of [multimedia technology] Flash. It was the best Flash site I think I’ve ever seen.

I feel really proud [of being a part of Okayplayer’s history]. Not only did they accept me and push me with graphic design, they accepted me and pushed me in music too. And when my interest in becoming a MC reared its head, Shawn Gee really started getting on me about the business of it. Let me give you an example. When I got down after a couple of months, I’m like, ‘Yo, I’m actually thinking I’mma start rapping.’ So, I’m thinking, all right, I’mma make a demo. Cool. I got to f**king Ahmir, I’m like, ‘Yo. Oh, you got beats? I think I’mma make a demo, I’m trying to get some beats going. You got some beats for me?’ And he’d be like, ‘Sure, sure, we about to go on the road, but when we get back, holler at me.’ I’m like, ‘All right, cool.’

They get back, I’m like, ‘Yo, what’s up Questlove, you got some beats for me, you got beats?’ He’s like, ‘All right, yeah, yeah, yeah, hold on.’ [He] leaves, and then Shawn Gee calls me into his office. He’s like, ‘Come here, man. You can’t be asking Questlove for beats, what are you doing? What do you have? You don’t have a thing.’ He’s like, ‘What is it worth to him to give you a beat? Stop doing this, you’re being annoying, that’s not what you’re here for. Do your job, stop asking for f**king beats.’

I’m like, ‘Oh s**t, I’m in trouble now.’ I thought he was going to fire me.

So, [The Roots] had a show in New York. I come to New York to help them and I’m still thinking I’m in trouble, so I’m extra on my P’s and Q’s, and I’m helping Questlove unload his drums, and he’s like, ‘All right, so Malik B ain’t coming to the show, so on this song you’re going to rap instead of his verse.’ And this was the Hammerstein Ballroom, it’s like 5,000 people. So, I’m like, ‘Word?’ If I made a mistake they wouldn’t just write me off. They would show me the right thing to do and then give me a chance.

Do you know why Okayplayer is referred to as ‘That Site?’ It’s, like, indirectly my fault. After I left Okayplayer and moved back to New York, me and my boy Ben [Detrick] started a record label/magazine called Loosie. Loosie had message boards as well, and pretty much all of our users were just New York Okayplayers and Philly Okayplayers. During that time, there were some technical difficulties — I think they were rebuilding the boards on Okayplayer — so they would crash every once in a while. And whenever they would crash, our boards would get flooded with usage. These were people from Okayplayer, and they would just come on our boards and talk shit about Okayplayer until the boards were fixed. Then, they’d all leave. It was like a mass exodus every time.

So, I got pissed off, and I’m like, ‘Don’t come over here just to talk shit about Okayplayer. Just don’t do that shit. It’s corny. If you want to come here, stay here, we got good discussions, we got different things to talk about, come and enjoy it. But don’t just come here, talk shit about them, and then go right back when they get fixed.’

At the time, the moderator of our board was Desus Nice, and [he] made Okayplayer a banned word on our website. So, if you actually typed in Okayplayer on our boards, it would change it to ‘#thatsite.’

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