History YMMV / TheLateShowWithDavidLetterman

* SeinfeldIsUnfunny: Letterman is undoubtedly one of the most influential figures in American comedy over the last three decades, and as [[http://www.huffingtonpost.com/noah-mallin/david-letterman-invented_b_5093509.html this article]] points out, he pioneered a lot of the ideas and attitudes that now saturate the Web. But because his influence is everywhere (not to mention SeasonalRot) he seems really passe these days. His early NBC shows come off a bit dry and awkward, and his peak period (the last few years at NBC and the first few at CBS) isn't easily available (though there's a fair amount of varying-quality Website/{{YouTube}} video).

* FunnyAneurysmMoment: [[https://en.wikipedia.org/wiki/Timothy_Treadwell Timothy Treadwell]] was once interviewed, and Letterman jokingly asked if he thought the bears would eat him one day. Treadwell would be mauled and eaten by a rogue grizzly. This scene was included in the theatrical cut of ''Film/GrizzlyMan'', but was left out of the DVD release.

* SeinfeldIsUnfunny: Letterman is undoubtedly the most influential figure in American comedy over the last three decades, and as [[http://www.huffingtonpost.com/noah-mallin/david-letterman-invented_b_5093509.html this article]] points out, he pioneered a lot of the ideas and attitudes that now saturate the Web. But because his influence is everywhere (not to mention SeasonalRot) he seems really passe these days. His early NBC shows come off a bit dry and awkward, and his peak period (the last few years at NBC and the first few at CBS) isn't easily available (though there's a fair amount of varying-quality Website/{{YouTube}} video).

* FunnyAneurysmMoment:
** When Margaret Ray committed suicide in 1998, Dave's older jokes about "that woman who keeps breaking into my house" turned into this.

** Zig-zagging between this and HilariousInHindsight, in February 2000, shortly after Dave had open heart surgery, Creator/RobinWilliams showed up wearing surgical scrubs and poked fun at the surgery. In 2009, Robin had open heart surgery himself, [[GallowsHumor and he poked fun at his, too]].

** Creator/CobieSmulders's appearances on the show were this after her character on ''Series/HowIMetYourMother'', Robin, was revealed to have made a song in the past about a secret crush she had, which in the end was revealed to be Dave's bandleader Paul Shaffer (who, like Smulders and her character, is {{Canad|aEh}}ian).
** Creator/JoaquinPhoenix's bizarre 2009 interview with Dave became this after ''Film/{{Joker|2019}}'', which sees him in an even thornier interview on a late-night talk show.

* FridgeBrilliance: Paul and the CBS Orchestra playing Music/LLCoolJ's "Hey Lover" as entrance music for [=supermodel=] [[Creator/ElleMacPherson Elle [=MacPherson=]]].[[note]]"L-L"/"Elle"[[/note]]
* FunnyAneurysmMoment: When Margaret Ray committed suicide in 1998, Dave's older jokes about "that woman who keeps breaking into my house" turned into this.

** Creator/JoaquinPhoenix's bizarre 2009 interview with Dave became this after ''Film/Joker2019'', which sees him in an even thornier interview on a late-night talk show.

* SugarWiki/HeartwarmingMoments: Letterman was a huge supporter of Conan O'Brien and, despite having acrimoniously left NBC, did everything he could to help Conan succeed as the host of ''Late Night''. He would even send over the ''Late Show'''s reserve audience to fill the seats in the early days when Conan was trying to find his footing and was so unpopular that no one would even accept a free ticket.
** For Letterman's final week on the show, he personally selected all of his guests--mostly old friends like Bill Murray who had appeared on the show many times. But for one show, he decided to have a particularly special person as the guest: Paul Shaffer himself, who left the orchestra and sat down for an interview with Dave. It's a perfect encapsulation of the men's friendship, and shows just how much Dave appreciated Paul for sticking with him for decades.
** Dave's annual Christmas tradition of having Darlene Love sing "Christmas (Baby Please Come Home)." He always gushed about her whenever she came on, and though the song's key lowered over the years as Love aged, she never stopped appearing. Similarly, Stephen Colbert announced that he ''wouldn't'' have Love sing the song during his tenure out of respect for Dave's own legacy.