I was a big fan of Letterman long ago too, before moving to Conan. He jumped the shark already in 2016 when he had Trump on and acted friendly then ambushed him to tell him his ties are made in Cambodia. It was down hill from there. He also started to reveal himself to be a huge degenerate around that time.
I think Letterman is one of the GOAT, since I grew up on him, and think Leno sucks.
He's number 2 on my list after Ferguson.
The sheer fact Letterman can say "managed media" in that clip with a straight face, tells you just how good he is at comedy and that he still got it.
I was a big fan of Letterman long ago too, before moving to Conan. He jumped the shark already in 2016 when he had Trump on and acted friendly then ambushed him to tell him his ties are made in Cambodia. It was down hill from there. He also started to reveal himself to be a huge degenerate around that time.
he is 100% don't meet your heroes type.