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9
Late Night Hosts (that I've seen) ranked

1. David Letterman (NBC era)
2. Johnny Carson
3. Conan O'Brien
4. Jay Leno
5. Tom Snyder
6. Sammy Maudlin
7. The guy with the robot sidekick
8. Any random Carson guest host
...
999. Stephen Colbert
I'd have to put Carson above Letterman. Johnny was faster and could get into quip exchanges with funny guests when Letterman would just have been laughing along with the audience. Letterman was a bit more in tune with the younger generations, though. But either of them could run circles around pretty much any of the other hosts I've ever seen. Conan was the only one funny enough to shine their shoes, in my opinion.

It's bewildering to anyone who saw Carson, Letterman, or O'Brien in their heyday to see the modern hosts like Colbert or Kimmel and try to understand what the fuck they're watching.
I concede my love of young Letterman probably relates to my youth at the time, which made Carson harder to relate to. In particular he would have these cringe old Hollywood guests on, doddering hags and codgers, whose films (at that time) I had never seen.

But yeah, those three were orders of magnitude more talented than political affirmative action garbage like Colbert and Kimmel.

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