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Watch Late Show with David Letterman Season 5 Episode 100 online — it may be available on legal streaming platforms such as YouTube, Netflix, Prime Video, Hulu, Disney+, and others.

Late Show with David Letterman: Almost halfway into the show, Dave suddenly leaves and gets into a cab that drives to Mexico, then San Francisco. Dave then boats across the Pacific, stops in Japan and sweeps the ice during an Olympic Curling competition in Nagano. Also in Nagano, Dorothy stumbles upon Bob Dole, while Biff searches for celebrity look-alikes.