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Late Show with David Letterman Season 7 Episode 89

Paul Schaffer, Drew Barrymore, Ray Romano

Backstage, Day 6: In the cold opening, Paul tries to hit on Drew Barrymore. Amongst the clips: Drew flashing Dave on his 48th birthday; Drew and Dave getting married one month after said clip; ten beautiful women present the Top Ten (see Show #0543); Ray Romano singing ""Silent Night"" as his kids beat each other up.

Feb. 14, 2000