Chance the Rapper is the coolest. He recently went undercover as a Lyft driver in Chicago. He did it all to raise awareness about the need to donate to Chicago Public Schools' arts programs.
He, also, is rumored to possibly be running for Mayor of Chicago. A press release has been sent out and it says there will be a press conference with Chance the Rapper regarding the Mayoral election.
Here is video of his time as a Lyft driver.