Mos Def & Dave Chappelle Did The Original Carpool Karaoke (Video)

For 25 groundbreaking episodes in the two official seasons Chappelle’s Show, viewers could lean back, laugh, learn, and maybe even cringe every so often. The program was about comedy, but it was hardly an escape. Instead, Dave Chappelle and his cast confronted real life issues with a humorous approach. Racism, poverty, addiction, and so many other facets of society were explored in sketch comedy, monologues, and a stack of memorable characters.

In addition to that, Chappelle’s Show was a musical oasis. At a time when Rap music and Hip-Hop seemed like two entirely different things, Dave put his friends and influences on TV. The program put Kanye West, Killer Mike, Slum Village, Freeway, De La Soul, Talib Kweli, and CeeLo in a major placement to get message music heard. Chappelle brought Mos Def and Kweli together, at request. He would later assemble The Fugees. Moreover, these performances never stuck to the formula of just the hits. It could be whatever, however—curated for an audience that valued different things than the mainstream.

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The first guest Chappelle ever had on his Comedy Central program was Mos Def. Yasiin Bey (as he is now known) made three different appearances on the show’s stage (as did ‘Ye and ‘Lib). He was the first musical guest, back in season 1, episode 2. Even when he was starting to become a Rap enigma, Mos loved transmitting with his friend (and appeared as an player too).

In his solo performance, mighty Mos rides shotty and performed “Close Edge” from The New Danger more than a year before it would release. Dave drives, and nods along with a focus, entranced with his friend spitting the illness, reworking some classic Grandmaster Flash & The Furious 5 on the chorus. The car moves through New York City at a time in both men’s careers that Heads seemingly can’t have back.

Just peep some of the Mos Def brilliance that rolls off the tongue.

Flood your city with the black ink flow / And my crew ain’t scared to let them things go / So, stop with the nonsense, ‘like he conscious’ / I’m just awake dog, I’m doing great, dog / I don’t play games so I don’t playa hate y’all / Get it straight or get the f**k up out my face, dog / I’m like the second plane that made the tower’s face off / That s**t that let you know it’s really not a game, dog / Your grind and my grind ain’t the same, dog / I’m the catalogue, you the same song.

Before “woke” was the slang, Yasiin knew what he was. Two years after 9/11, he courageously used the event to drive in emphasis on his poetry.

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#BonusBeat: The album version, which would be the second single, officially:

This song is produced by Minnesota.