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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

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21
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.
What distinguished Letterman from Carson was the element of chaos. Carson was too professional and powerful for anyone to truly defy him in his arena. Letterman was a bit of a goof, so people felt freer to mess with him.

Thus for me it was a much more interesting show. I don't think any actress ever flashed Johnny on the show. Not even sure anyone climbed on top of his desk.
one thing about Craig Ferguson
(the guy w/ the robot sidekick)
is that he had quite the knack for having
flirty interviews w/ sexy actresses
there's a number of this type of interview on youtube...

beyond that he also was a pretty good LNH
was glad to see he made your List

and yes Colbert can fuck right off !