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Hidden cameras show Chance picked up passengers while wearing a knit cap and sunglasses to disguise his appearance. They chatted about the city, life and music, and cracked jokes until they reached their destination.
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That's when Chance swapped the beanie for his signature 3 cap and took off the sunglasses, shocking his riders as they found out who they'd been talking to the whole time.
Desiree Hemphill-Davis was one of those riders. When she opted in to "round-up-and-donate" in her Lyft app a year ago, she never thought it would lead to what has become the "ride of her life."
"A lot of my friends, I think, are going to see the video and say, 'There's no way you could not have known,' but I definitely did not," Hemphill-Davis said.
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A few weeks ago, Hemphill-Davis got into a Lyft and was introduced to a driver named "John."
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"Just talking about what it was like growing up in Chicago and our shared experiences, hopes and dreams, that sort of thing. Then we started talking about local music," Hemphill-Davis said.
Little did she know, "John the Driver" was actually Chance the Rapper.
"He takes off his hat and says, 'Well I'm Chance the Rapper' and I just kind of lose it at that exact moment," Hemphill-Davis said, laughing.
Lyft's "round-up-and-donate" feature rounds up fares to the nearest dollar and donates the difference to a charity of the rider's choice. Last year, Lyft teamed up with Chance's nonprofit, SocialWorks, and featured The New Chance Fund in its "round-up-and-donate" feature.
"People can round-up-and-donate and then give back to CPS through our new Chance Fund," said Essence Smith, of Social Works.
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SocialWorks donates money for arts education to Chicago schools in need. The New Chance Fund, which SocialWorks launched at the beginning of the 2017-2018 school year, will help 20 CPS schools give kids better access to enrichment programs during the school day.
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Hemphill-Davis was one of the riders who opted in to donate to Social Works.
"It was just a simple way to donate to Chicago Public Schools. It was something I wanted to do because I'm a product of Chicago Public Schools," Hemphill-Davis said.
Lyft officials said on average, each rider donates a few dollars each month. Since the partnership between Lyft and Social Works began, the nonprofit has raised more than $100,000 for CPS students and programs.
Click here for more information about Round Up and Donate.
Click here for more information about The New Chance Fund.
Click here for more information about SocialWorks Chi.