The digital space today is completely different from the late 90’s and early 00’s. With platforms like Instagram and TikTok, and outlets like Complex and Genius, getting your work out there is more accessible than it’s ever been. A 15-second Instagram reel can get you seen by A&R reps, a 30-second TikTok dance can get your song charting on Billboard. Success is at the palm of our hands and can be quickly attained simply by tapping “post”.
But where did artists go in the late 90’s/early 00’s? How did they get their voices heard without the tools that we have today?
There’s one mastermind behind it all, Ahmir Thompson, also known as Questlove, drummer and co-frontman from the legendary rap group The Roots.
In late 1998, The Roots were getting prepared to release their 3rd studio album, Things Fall Apart, which featured the hits “You Got Me” ft. Erykah Badu and Eve, and “Act Too (Love of My Life)” ft. Common. During this time, the online world as we know it today was still taking baby steps.
We witnessed the birth of Google, making them an immediate competitor with Yahoo. At the same time there was a huge shift in how people explored the internet, what started as just a list of websites shifted to algorithmic search, changing how people found music, forums, and culture online. While music streaming platforms didn’t exist yet, mp3 formatting was moving in like a storm, preparing for the Napster boom in 1999.
While it was becoming easier for music lovers to find their community, The Roots struggled to find an online community that they belonged to. They didn’t really fit into the commercial rap lane, and their sound aligned more with jazz, soul, and live instrumentation. So what website, what blog, what forum could the legendary Roots crew align themselves with in 1998?
The real answer? Not a single one.
While it was Questlove that sparked the conversation of building a website for The Roots, it was Angela Nissel, recent graduate of the University of Pennsylvania who later became the writer and executive producer for the hit TV show Scrubs, that suggested that they create message boards on the website for connection, discussion, and debate (1). An idea that left the greatest impact for many musicians to come.
Since this was a time where anybody and everybody felt like they needed and/or wanted a website, domains were being taken left and right. Of course, theroots.com was already taken, so the group had to get a bit more creative when coming up with their domain name.
The Roots are from Philadelphia, Pennsylvania and consistently pay homage to the city of brotherly love through their work (i.e. their 1996 album called “Illadelph Halflife”). The website was another opportunity to do so.
A popular term in Philly slang is “Ok, Player!”, similar to today’s AAVE saying “I see you!” or “Playa playa from the Himalayas”, a popular line from the 1992 sitcom Martin. So, to pay homage to the city and have true representation, Questlove and Angela Nissel settled on okayplayer.com.
On February 23rd 1999, Questlove and Angela published okayplayer.com, the same day that The Roots published their 3rd studio album Things Fall Apart. This album won a Grammy for Best Rap Performance by a Duo/Group (You Got Me) and was nominated for Best Rap Album in 2000.
Again in 1999, D’Angelo was preparing to release his second studio album Voodoo. And since D’Angelo is a Soulquarian (a collective that consists of Questlove, J Dilla, D’Angelo, Erykah Badu, Bilal, Yasiin Bey, Common, and Q-Tip), the Okayplayer community received something special. A few months before the album was released, Questlove posted a track-by-track breakdown of the album on the website, something that had not been done before (2). This gave fans something to look forward to and speculate about on the forums leading up to the release of the album. At the time of publishing, the album was not yet finalized, meaning there were some songs that were left off the album but had a breakdown from Questlove. That song was a feature from Lauryn Hill and produced by J Dilla (2).
And while this was going on, Okayplayer made another major move, The Okayplayer tour (3). A blog/forum site with a tour? Unheard of.
This tour had The Roots headlining with supporting acts like Rah Digga, Common, Talib Kweli, Black Eyed Peas, Yasiin Bey (Mos Def), Bahamadia, and more (4). It ran through October and November of 2000 with 40+ stops. The tour was wildly successful with several sold out dates across the United States.
The tour ended at the end of November in 2000, and on January 1st 2001 D’Angelo’s sophomore album Voodoo was released. Boom. Back to back impact on the music community yet only two years of existence.
While these are all big moments for pre-established artists, Okayplayer was also a place where music lovers were able to turn into musicians.
Nicolay discovered Okayplayer through the liner notes of his favorite albums, Voodoo and Like Water For Chocolate by Common, and made a connection with Phonte through the forums. Phonte and Nicolay both resided in different countries when they first connected, and with similar music interests, they began collaborating on original music by sending digital files to one another back and fourth over the internet, resulting in their duo name being The Foreign Exchange (5).
Kelly “K-Fresh” Frazier, posting under the name RenaissanceSoul, was known for keeping a running discography of J Dilla records on the website. He now has a podcast called Fresh Is The Word. User Desus Nice (½ of Desus & Mero) made appearances on the OkayPlayer forums, sharing stories with an intense skill for writing paired with entertainment (6).
And while Okayplayer is a space of community and discourse, there was also room for constructive criticism. Whether it was a discussion about the change in Q-Tip’s style or questioning Common’s work, there was always a space for healthy discourse to occur (7).
Since February 23rd 1999, Okayplayer has been making non stop milestones and expansions to the website that benefits their core audience and artists that they’ve inspired over the years. In 2004, Questlove launched OkayPlayer records which opened the doors to artists all over the world (8). In 2013, OkayAfrica was launched. In 2024, OkayFuture Labs was launched as an educational resource on hip-hop production, offering exclusive beat packs, virtual instruments, sample packs, and vinyl records. In that same year, Okayplayer NYC launched a local culture, music, and nightlife vertical of Okayplayer, covering the best NYC Hip hop nights, live concerts and neighborhood nights.
Over 27 years, Okayplayer has consistently left its mark in the world of music and journalism. The platform not only informs and educates but it also creates safe spaces for those exploring unfamiliar terrain. There is so much more ahead.
Citations:
1 Dan Charnas, Dilla Time: The Life and Afterlife of J Dilla, the Hip-Hop Producer Who Reinvented Rhythm (New York: MCD, 2022), 183.nm
2 Charnas, Dilla Time, 188.
3 Charnas, Dilla Time, 198.
4 Grouchy Greg Watkins, “Okayplayer Tour Kicks Off,” AllHipHop, April 2004, https://allhiphop.com/news/okay-player-tour-kicks-off/
5 Charnas, Dilla Time, 238.
6 Charnas, Dilla Time, 238.
7 Charnas, Dilla Time, 189.
8 Gail Mitchell, “The Roots Launch Okayplayer Records,” Billboard, January 26, 2004, accessed article