After an accumulation of entertainment industry propaganda and having to face the unfortunate reality that his race sketches were being laughed at for the wrong reasons, a distraught Dave Chappelle relieved himself from the spotlight in 2003 to pursue a much-needed hiatus. After a brief stint in Cape Town, South Africa enjoying life where no one knew or cared who he was, Dave returned home ridded by the stress of his Comedy Central debacle as the Bigfoot of comedy. Having been a ghost for over a decade, we have only been blessed with but a handful of rare appearances in recent years from arguably the funniest man alive. Until now.

“Technically I never quit, I’m 7 years late for work.”

Upon his return, Dave wasted no time getting back to his roots with the help of Questlove and the gang, putting together a hip hop Justice League (much like the one at his famous block party in 2005) and a full piece orchestra to perform with him at Radio City Hall. During his week of stand-up in New York City, Dave blessed his fans with performances by Erykah Badu, The Roots, Busta Rhymes, Kanye West, Black Star, and Nas who delivered the entirety of his seminal classic Illmatic.

“Comedians and musicians are like this [interlocks hands]: every comic wants to be a musician and every musician thinks they’re funny…It’s a very strange relationship we have…Mos Def: funny guy. Jamie Foxx: good singer and piano player…I’m mediocre at both, but I’ve managed to talk my way into a fortune.”

Having understood the connection and importance of bridging the two worlds of comedy and hip hop, Chappelle has always made a strong effort to provide an outlet for such collaboration. It was Dave Chappelle who gave Kanye West his first TV appearance and took his block party to the influential Bed-Stuy neighborhood of Brooklyn. Whether it was by incorporating rap legends in his infamous sketches or ending episodes of Chappelle’s Show with live performances from some of the most influential hip hop acts of the time, he gave them a platform to show the world their true colors, unhitched from industry pressure — what Chappelle despised the most.

But Chappelle does more than just promote hip hop: he strives to have it presented in the light it deserves. With so many negative connotations strapped to its back, the genre continues to be weighed down by those who don’t understand its subtext and importance.

During his documentary Dave Chappelle’s Block Party, Chappelle and his crew interview a corky Caucasian couple at the beginning of the film about their take on rap music, during which the wife noted, “I don’t like rap music because rap music composes a lot of foul language for children… I don’t even think it’s proper for adults to be using that type of language, either.” After a day of uplifting music stemming from the souls of each hip hop artist invited, Chappelle cuts the interview back in at the at the end of the film as a simple juxtaposition to prove how wrong people often are about a genre so constantly misconstrued.

“The more you say with it, the less airtime you get — guys like Dead Prez say it all…‘The white house is the rock house, Uncle Sam is the motherfuckin’ pusha man/what I gotta do to make sure you understand?’ You know they don’t wanna hear that on the radio, but you hear it in the barbershop all the time.”

Whether it was on his show or in one of his sponsored concerts, Chappelle always made sure his acts reflected the best hip hop had to offer: musically, lyrically, intellectually, soulfully. Chappelle lived by the mantra that the message less-heard was the most important. Through the dual outlets of comedy and music, he took it upon himself to shepherd these ideas to the public in a way that was both accessible and hilarious.