Chance The Rapper Goes Undercover As Lyft Driver To Raise Money For Chicago Schools

STUDIO CITY (CBSLA) — Even if you're a Grammy Award-winning rapper, sometimes you have to get a side gig.

That's what Chicago-based artist and philanthropist Chance the Rapper had to do, but it was, in reality, all for a good cause. The ride-hailing service Lyft on Monday posted a video of Chance picking up riders throughout the day, making small talk in the car, as one does. He even tries — and fails — to spit a freestyle as his Lyft alter-ego John.

WARNING: The following video contains strong language:

Undercover Lyft with Chance the Rapper by Lyft on YouTube

"What kind of music do you listen to?" the rapper, wearing a beanie and sunglasses in the most basic of disguises, asks his passengers. The getup worked, since several of them said Chance was one of their favorites.

"Chance the Rapper.[...] Oh, Kendrick [Lamar], also one of my favorites," says one woman.

"Kendrick is really good. Is he better than Chance, though? That's the real question," Chance comes back.

"It's real cool that, like, his mom is supportive, and he married the love of his life," she continues, maybe evading the question.

"I bet Chance has a good mom. He's probably getting married, too," the rapper says bolstering his own family man bona fides. "I'm not a super-fan, but I know he's got a good-looking woman, think he's about to get married to her."

The jig is up eventually, and Chance confesses, revealing his signature "3" baseball cap in Lyft-brand pink.

It's a story those riders will probably tell for a long time, the result of a partnership to raise money for Chicago Public Schools between Lyft and Social Works, an organization whose stated goal it is "to empower the youth through the arts, education and civic engagement."

The app allows riders to have part of their ride fees go to a charity of their choice.

It's just the latest in "Chano's" brief history of philanthropy and social entrepreneurship in Chicago. Earlier this month, Chance announced he was donating $1 million to help Chicagoans connect with mental health agencies. Back in July, he performed for free at the 50th Anniversary of the Special Olympics, which originated in Chicago.

However, Chance's work has not always been about niceties. He has been an outspoken critic of Chicago Mayor and former Obama Chief of Staff Rahm Emanuel, who famously walked out of a city council meeting when Chance openly criticized the city's plan to build a new, nearly $100-million police academy as the city faces massive public school closures.

He demanded Emanuel's resignation in a batch of songs released this summer, in which he also announced he was buying the local news site Chicagoist. Emanuel has since said he will not be seeking reelection as mayor. The Chicago Sun Times said Monday that, to the disappointed of many of his fans, Chance would not be running for mayor, but that he "is looking to add some juice to the race."

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