One of the most relaxed moments of the whole segment is when Letterman suggests that he will hang out with Pekar after the show and eat the donuts that Pekar brought with him to the taping.
There was a clear turning point during his appearance on the July 31, 1987 show, when he appeared wearing a shirt that read, “On Strike Against NBC.” Around this time, he started using his appearances to talk out against General Electric, which owned NBC, and he seems more visibly annoyed by Letterman’s usual questions. When Letterman asks him how Cleveland is doing, Pekar scoffs that it is a “stupid question” and he knows it. He also calls talk show entertainment “simple-minded bulls—.”
When they come back from a commercial break, Pekar jumps right into GE, and Letterman calls his behavior “very bad manners” and tries to shut it down with jokes.
Things took a really dark turn during the August 31, 1988 appearance. Letterman loses his patience entirely, saying that Harvey was wrong in what he was saying and repeating that his show was “not the place” for this discussion.
