Elle MacPherson, Vince Vaughn, Jewel

Late Show with David Letterman – Season 4

Remote on the 14th Floor: Late Show staffers Eric Stangel, Matt Roberts, Bob Borden, Rodney Munoz, Christian Breheney, and Eric Kaplan relate their Prom Nightmares while eating in the coffee room, with dramatizations that include Rupert Jee and Richard Simmons.