Troy, while I agree with you that Letterman ultimately won over the Late Show 's studio audience , the dominant emotion in the crowd (and on my couch) was confusion. The strangest thing about Dave's confession was that in his repetition of the phrase "creepy things," he left it entirely unclear whether he actually believed that he had done any "creepy things." The segment — coming as it did after a monologue packed with bad skunk jokes — was so unexpected and internally incoherent that it was impossible to tell what was supposed to be a laugh line and what wasn't. The crowd, understandably addled by the tragicomic proceedings, perceived Letterman's use of "creepy things" as a running gag, and Dave didn't make any attempt to tamp down the laughter. Yet by the end of the segment, he was asking why everyone was guffawing.
Does Letterman think he committed a serious transgression? The main reason it was hard to tell whether he was taking it seriously — and whether we should take it seriously — is that he stayed mum about how many of his female staffers he'd slept with and when the affairs had taken place. When the Late Show host said that the admission was embarrassing and that he needed to protect his family, the implication was that it was a big deal. When he followed that up with a crack about how it was more embarrassing for the women, it seemed like he was popping a balloon he'd just spent 10 minutes inflating.