I just saw an episode of "The Larry Sanders Show" that IMDB tells me was from 15 Sep 1993. The guest stars were Elizabeth Ashley, Gene Siskel, Warren Zevon, and John Ritter. These are not old people, but ten years later, three of the four (all except the oldest) are dead. Two of them died 8 and 4 days before the 10th anniversary of the original airing of the episode.