It’s almost as if renowned drummer Ahmir “Questlove” Thompson (of The Roots fame) and decorated television writer Angela Nissel could feel the pulse of the times; moving their musical collective Okayplayer to the World Wide Web in 1999 changed the landscape of the internet. Evolving from a blog centered around The Roots to becoming an irreplaceable online community, Okayplayer (or OKP, for short) was the online center for fans of neo-soul, underground rap and everything in that stratosphere to bond, talk to their favorite artists, build friendships and create together. On Okayplayer’s 25th anniversary, we’re looking back at just how impactful the site has been.
Rap music in 1999 into the early 2000s has been unfairly viewed as warring factions, as mainstream rap and their underground counterparts found success at the same time. When Eminem, Nelly, DMX and Jay-Z were etching their names in the record books, Yasiin bey (fka Mos Def), Common and The Roots were creating timeless music of their own. Of course, there were also artists, like the inimitable OutKast, who existed at such a large scale that they fit into both worlds. Even though Okayplayer was more attuned to rap that was off of the beaten path, there was room for fans of the biggest commercial stars there. OKP wasn’t only a home for rap; the website was instrumental in the then-burgeoning Neo Soul movement.
D’Angelo’s Voodoo dropped in 2000, as did Erykah’s Mama’s Gun, and both were huge on OKP. The musical sensibilities of these artists, both of which are mired in funk, the blues and vulnerability within their lyrics, directly aligned with those of your typical Okayplayer member. Both albums are Neo Soul monuments, and helped elevate a musical genre that was soaring with no signs of slowdown. Lauryn Hill and Maxwell were two of the genre’s earliest superstars, with Alicia Keys coming along in 2001 and taking the world by storm.
Okayplayer’s first five years required dedication, resilience and belief in the community. The site and message board went on to become the stuff of legends, and it all started with Questlove and Angela not only taking a chance on themselves, but believing in the power of the early internet.
By 2004, rap’s relationship with the internet started to become more intertwined. The web was turning into a breeding ground for learning more about rap scenes worldwide, along with being a place to trade music. As the internet surged, so did underground rap, allowing artists who were burgeoning stars in niche scenes to stretch further than anyone could have imagined. Acts like MF DOOM, J Dilla, Slum Village, Justus League, and more surely benefitted from the internet, and OkayPlayer was one of the vehicles for that. OKP was starting to hit its stride now, and the timing could not have been more perfect.
Some household names made noise from 2004-2008, one continuing with their previous momentum, and the other breaking out as a superstar rapper and producer. The Roots dropped The Tipping Point, Game Theory, and Rising Down in those 5 years, continuing to evolve their sound. Out in the Midwest, Chicago’s own Kanye West released his debut album, College Dropout, Late Registration, Graduation, and 808s & Heartbreak, four great albums that formed the core of his career.
Okayplayer also took a step into the real world in 2008, the year of the first-ever Roots Picnic. The Philly music festival not only served to showcase The Roots and other talented acts like J*Davey, Santigold, and Gnarls Barkley; it also allowed OKP message board members to meet up in one place. The online community was now tied to a yearly event that would only grow larger. These five years were a great time in music, as new talent popped up left and right, with a solid amount of them standing the test of time.
In the five years of 2009 to 2013, hip-hop was going through a changing of the guards. The power of social media and platforms like YouTube was becoming evident, with the lowered barrier of entry allowing a lot of young upstarts to break through. A new vision of west coast rap was taking hold as rap stalwarts turned global Top Dawg Entertainment, and the talented troublemakers known as Odd Future began to take off. There were also solo acts that carved their own niche in the rap game: acts like Drake, Chance The Rapper, Wiz Khalifa, Curren$y, Kid Cudi, A$AP Rocky and more. The blog era encapsulated a variety of styles and sounds, and the artists of that time are still inspiring artists now.
Top Dawg Entertainment, the California record label, fully burst onto the scene in 2012 when Kendrick Lamar dropped a classic in good kid, m.A.A.d city. This began their run as the lyrical rap label that everyone else was chasing, buoyed by the talents of the aforementioned Lamar, ScHoolboy Q, Ab-Soul and Jay Rock. All four rappers brought something different to the table, and captured the attention of hip-hop at large.
At the same time, Odd Future, also from Cali, were a group of wild teens and adolescents making shock-value rap. Behind the crazy videos and graphic, horror-core adjacent lyrics, there was raw talent, whether it was from the crew's de-facto leader Tyler, The Creator, Earl Sweatshirt or any of OF’s many members and affiliates. Both TDE and Odd Future would produce one-of-one R&B/pop stars, with TDE being the home of SZA, a clear superstar, while Odd Future was the ever-mysterious Frank Ocean’s first taste of widespread popularity.
Chance The Rapper’s offbeat, jazz, gospel, and R&B-tinged rap turned him into a star and media darling quickly, as there was simply no one like him. By the time the Chicago rapper dropped his game-changing mixtape Acid Rap in 2013, he was everywhere, a standout artist amongst a sea of look-alikes. He existed in an era where artists felt comfortable being themselves, no matter what kind of music they made.
Of course, OkayPlayer’s favorite group, The Roots, were still hard at work. In 2010 and 2011, the band would release How I Got Over and Undun, respectively. Both albums would be well received as The Roots sound continued to twist and change with the times. Even as rap and music at large went to new places around them, The Roots remained true to themselves and marched to the beat of their own drum.
This was also a major time for commercial rap, as some of the genre’s biggest stars made their mark. Young Money, Lil Wayne’s rap crew that featured a budding Drake and Nicki Minaj, had two Billboard Hot 100 hits in “Every Girl” and “BedRock.” Jay-Z and Alicia Keys’s “Empire State Of Mind” was the number one song in the country for five weeks that same year. Kanye West would go on to drop what is widely considered his magnum opus, My Beautiful Dark Twisted Fantasy, in 2010, just two months after Pittsburgh newcomer Wiz Khalifa would score his first No. 1 hit with “Black And Yellow.” If there was any time that was perfect to make a name for yourself in rap, it was then, where veterans and brand new names found new ways to rise higher.
In the world of music, 2014-2018 was a fun time. The upstarts of recent years, like Kendrick Lamar and J. Cole were turning into superstars and Atlanta hip-hop was moving into a new era of dominance, thanks to Migos, Future, Young Thug, and more. Drake had the most dominant career stretch, Donald Glover spread his wings as a multi-hyphenate and Rihanna, Beyonce, and SZA took over the charts. Rap veterans like Jay-Z and Roc Marciano reinvented themselves and The Roots continued rolling. On top of that, rap crews like the A$AP Yams and A$AP Rocky-helmed A$AP Mob, the Pro Era, Flatbush Zombies, and The Underachievers link-up Beast Coast, and Vic Mensa’s SAVEMONEY (which also included Chance The Rapper) rose to prominence.
Hempstead, Long Island native Roc Marciano, and Brooklyn’s own Jay-Z both found themselves between 2014 and 2018. Roc had already put the streets on notice after his 2010 album Marcberg, and even more so with Reloaded in 2012. But his stretch from 2017 into 2018 where he dropped Rosebudd's Revenge, its sequel, RR2: The Bitter Dose and Behold a Dark Horse showed the world that he is a special talent and an inarguable pioneer of street rap. With the dark minimalist beats, and the conversational flow woven with clever turns of phrase and wisdom; he is simply the best at this often-copied style. Jay-Z, long a rapper who was more than happy to rap about the spoils of his success, began to look back on his past with a different eye when he dropped 4:44 in 2017. An album about his infidelity within his marriage, the birth of his daughter, racism, and wishing he made better decisions in his youth was a coming of age moment for him, a far cry from the same man who made “Big Pimpin.” Jay revealing so much about himself was a curveball at the time, and 4:44 became a great moment in the later stage of his career.
Rap’s ecosystem is truly something to behold, as so many different sects of the genre were blowing up in these five years. Kendrick Lamar was already a media darling by 2014, but his release of To Pimp A Butterfly in 2015 and Damn in 2017 took him to another stratosphere. J. Cole was in a similar position, releasing his most-acclaimed album, 2014 Forest Hills Drive, and later, KOD in 2018. In Georgia, Migos were stacking up hits and dropped a game changer in Culture, Future released DS2 and was fully into his star turn, Young Thug was turning his potential into real success and Donald Glover was making his presence felt through TV (Atlanta), rap (“This Is America”) and funk (Awaken My Love). Drake, already a superstar, started to run away with the lead in this era, dropping No. 1 projects (Views, More Life, Scorpion, etc.) and multiple diamond singles.
This period was also major for the ladies, as Rihanna dropped Anti in 2016, Beyonce released Lemonade the same year and SZA dropped the career-defining Ctrl in 2017. All three of these singers are superstars in their own right, releasing music that has stood the test of time. They all coexisted, with each of them showing love to the other; it was also a clear turning point for all three acts. Rihanna hasn’t put out an album since Anti, Beyonce hit another gear with her releases after Lemonade and SZA turned into an arena-filling songstress off the strength of Ctrl.
Of course, the heart of OKP, The Roots crew, had an album in 2014, titled ...And Then You Shoot Your Cousin. The band hasn’t released an album since, but are on television nightly as the house band for The Tonight Show Starring Jimmy Fallon, along with appearing at The Roots Picnic every year. OkayPlayer lives on, and so do The Roots.