February 24, 1997
In his first Oprah Show appearance, Chris didn't get top billing. Instead, Oprah first interviewed Li'l Penny, the popular pint-size puppet—voiced by Chris—who appeared in NBA star Anfernee "Penny" Hardaway's Nike commercials.
When Chris finally did get his proper introduction, he delivered some of the outrageous jokes that earned his second album, Roll with the New, a Grammy in 1998. "Do people owe you money and still have the nerve to buy clothes around you? Like, 'Hey, look what I just picked up?'" he said. "Did you see my money while you were down there?"