Has anyone ever found the interview where Conan supposedly upset Eartha Kitt? There are some instances (notably the Ireland segment with the kids) where he talks about it being unpleaseant interviewing her.
This would have been from some time between 1998 and 2002, probably on the earlier end. There was a female guest (who I believe was an actor) that was on late night. She talked about how a Dr. Seuss book was based on her. There also might have been references to Star Trek. All that I remember is that it was hilarious. Conan made a joke about how the book was creepy and the actress was almost in tears from laughing so much. It was classic Conan and really made me like him as a comedian.
I just remembered he also made a joke about editing the interview to make the person who was being interviewing look crazy.
Edit: My best bet for the book is “Daisy-Head Mayzie” because I remember a girl on the cover. The timeline also makes sense.