20. Dave Chappelle
When Dave Chappelle appeared as himself on “The Larry Sanders Show,” he’d recently come off his own project, aptly named, “The Dave Chappelle Project.” This was before Chappelle was in the movie “Half Baked,” and long before his famous “Chappelle’s Show.” “The Dave Chappelle Project,” parodied in the episode where he appeared, only aired one time; the pilot. Chappelle walked from that project when producers suggested his show needed more white people. We know who won that battle in the long run.
19. Ellen Degeneres
When Ellen appeared on the show, she was not yet out about her sexuality. Fans will remember that Degeneres was one of the first openly lesbian performers at a time when most actors lived with their sexuality as a secret or a mystery. On the episode of “The Larry Sanders Show,” Shandling’s character intends to out her, but he’s not sure if she’s actually lesbian. Comedy ensues. Degeneres is so big today, one only need to know her first name, Ellen.