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David Letterman era:

  • "Funny Aneurysm" Moment: In Don Rickles' first appearance on the show in 1983, Rickles, while musing about death, made a joke about how he estimated around 40 cars would show up at his own funeral when he died, while for Letterman's he figured "one wagon and the black kid" — referring to Hiram Bullock, then the guitarist for the in-house World's Most Dangerous Band. Unfortunately, while Letterman is still alive as of 2020, Hiram Bullock is not — he passed away from cancer in 2008, and Letterman paid tribute to him on The Late Show.
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Seth Meyers era:

  • Crosses the Line Twice: Dips into it now and then.
    Seth: That's right, the election is tomorrow, and Roy Moore is already setting up for his victory celebration! [Picture of Chuck E Cheese's]
  • Growing the Beard: Viewers were immediately struck by how visibly uncomfortable Seth was with things like stand-up monologues and sketches. Once the show began to become a news-centric program with an increasingly political take on things and Seth began performing exclusively from behind his desk (with the studio redesigned as a result), his run garnered more acclaim, particularly for his "A Closer Look" segments which were seen as honest, simple breakdowns that got to the meat of an issue, especially in the tumultuous 2016 election and ensuing presidency.
  • They Wasted a Perfectly Good Plot: Some viewers were surprised that Trump was not mentioned at all when Seth had "El Chapo" (played by Horatio Sanz) on the show in January 2016, considering the unconfirmed threats El Chapo had made against Trump and the meme narrative of their beef.
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