8. Rupert Jee
In 1993, the co-owner of Hello Deli on 53rd Street learned that his new neighbor would be interviewing him as part of a get-to-know-you segment for the show. "I was so frightened about being on television, I was just hoping that they would forget about me," Rupert Jee later recalled thinking. No such luck: He soon became a staple of the show, and an example of the somewhat warmer, more amiable vibe that the Late Show had over Letterman's Late Night tenure. The host's favorite trick was to have Jee do remotes in disguise while he gave him instructions on what to say to strangers via walkie-talkie. But the best bits were simply Dave shooting the breeze with the shy, personable man, encouraging him to take a lot of unsolicited business advice. (For the record, installing the Slurpee machine was a great idea; giving out free hot chocolate in the winter, less so.) During his final appearance, Jee even got his own Top 10 list — a fitting way for the Hello Deli proprietor to say goodbye.