- David Letterman (Self - Host)
- Paul Shaffer (Self -Musical Director)
- Alan Kalter (Self - Announcer (voice))
Episode: Lennox Lewis, Dr. Bertrand Piccard & Brian Jones
Air Date: 1999-04-07
Throughout the night, local teens with learner's permits parallel park on 53rd Street. At the end of the show, Dave attempts parallel parking and nearly embarrasses himself.