Jennifer Aniston, Jerry Springer, Al Green

Late Show with David Letterman – Season 5

Amongst the festivities of ""Chicago Night"": Jerry Springer's bouncers stand on opposite sides of the stage; The Man Not on Fire appears in an ad for Gold Coast Drugs; the Top Ten home office is temporarily moved to nearby Schaumberg, Illinois; local blues singer (and frequent guest) Taj Mahal presents the Top Ten; Bob Borden goes on a frantic pursuit through the Windy City attempting to get an interview with Oprah.