Dave Chappelle has made a career out of making people laugh—and think. He has that same ability when crossing over into music. Over the years, Chappelle has made guest appearances on a variety of songs. The three outlined below are more recent endeavors by three different rappers delivering distinct messages, with Chappelle elevating those meanings through the art of spoken word.
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1. “Parasail” by Travis Scott
This dreamy track is not one you’d expect to hear on a rapper’s album. In addition to rapper Yung Lean, comedian Dave Chappelle also makes an appearance on the deep cut, “Parasail,” off Scott’s 2023 album, Utopia. Chappelle’s signature smoky voice welcomes listeners in as he opens the song by reprising the phrase, “I fall, I get up,” three times over before affirming, “I stand tall.”
Scott then intriguingly layers his disoriented voice over a subtle jazz-leaning melody until Chappelle’s voice comes back in at the end, I forgive myself/I choose to feel good/I choose to feel free/I will fight for everything I love, forever/And I will love everything that I fight for, forever, he encourages listeners.
“Parasail” marked a pivotal moment in the comedian’s career, as it’s the first time he’s appeared on the Billboard Hot 100. Following the album’s July 28 release, “Parasail” reached No. 53 on the genre expansive chart.
2. “Story” by Dave Chappelle (Big Sean)
Big Sean’s 2020 album, Detroit 2, blends music with the art of storytelling. The rapper exemplifies this by having Dave Chappelle deliver a spoken word monologue in the middle of the album titled “Story.” For nearly three minutes, the comedian tells one of his favorite stories of being in the city of Detroit where Big Sean was raised. “One of the reasons that Detroit is my favorite market is because audiences in Detroit, for a comedian, I find them to be particularly challenging,” he says over a gentle piano melody.
He goes on to share a memory of when he met an older man backstage at one of his shows, along with famous Detroit rapper Danny Brown. He and Brown smoked a mysterious substance that led to Chappelle bombing onstage. But when he got back to his dressing room, he received an encouraging speech from the older man who happened to be Big Sean’s father.
“He gave me a pep talk that only a dad could give and it made me feel wonderful,” Chappelle recalled. “Shout out to you Big Sean, shout out to Detroit, I’ll never stop loving your city and I’ll never stop loving you, bro.”
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3. “Run” by Killer Mike ft. Young Thug
Rapper Killer Mike makes a bold statement with the intro of his song “Run” from his 2023 album, Michael. The song opens with a monologue by Dave Chappelle, who encourages the rapper to keep moving forward in life at all costs. For just over a minute, Chappelle’s commanding voice gives listeners into Black history, comapring being a Black man in America to being a soldier in the Normandy landings during World War II.
You’re just as heroic as those people that stormed the beach/So what’s your excuse? I’m not good enough, I did something wrong, I’m not perfect/Nobody asked anyone to be perfect/You’re just asking people to be honest, Chappelle advises calmly over a booming melody led by a horn section.
The intro was inspired by a similar monologue that Chapelle gave to Killer Mike backstage at one of the comedian’s shows when he encouraged him to run for governor of his state. “Then he gives me a speech that has me beaming afterward,” Killer Mike recalls to Complex. “Not that I wanted to run for office, but it helped me to have a greater understanding of what I represent for many in the culture—a truth-seeker, a truth-teller, and firmly on the side of the people. I was honored by that.”
Photo by Brian Stukes/WireImage
