- Harsher in Hindsight: In a case of History Repeats, NBC underwent another battle over the next host of the Tonight Show between Leno and Conan O'Brien (which inspired a sequel book by Carter The War for Late Night).
- Moral Event Horizon: Leno is forced to choose between keeping The Tonight Show or parting with Helen Kushnick, a long-time ally from his early stand-up days. When he tries to get her to back down for both their sakes, she explodes in a rage and accidentally reveals she was responsible for an ad campaign to push Carson to retire. Because Leno swore to Carson - his beloved Father figure - that he had nothing to do with that, he realized Kushnick made him lie to Carson, which immediately ends any friendship he had with her.Leno (seeing Kushnick is trying to smash a framed picture of the two of them): What? You want this broken?! (grabs it from her and smashes it with full fury) IT'S BROKEN! (walks away)
- Questionable Casting: Zig-zagged for the made-for-TV movie. While some roles were cast nicely (John Michael Higgins as David Letterman was spot on, and Kathy Bates played a great Helen Kushnick), Daniel Roebuck wasn’t exactly Jay Leno’s mirror imagenote , and the same goes for Rich Little as Johnny Carson (though Little had long been acclaimed for his vocal impression of Carson, which is probably why he was chosen).
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