Headlines was pretty cool back in the day. I think when they did it on a permanent night, Monday's or something, was the only time I ever watched The Tonight Show (other than Conan's final meltdown week) enough to be considered "regular watching." (And I had no cable in my room so it was like watch that bit, watch Night Court re-run on some other channel, watch Conan bits, back to reruns/infomercials.) This was like during the dial-up/early DSL days so you had plenty of down time waiting for all the garbage like Quake sounds to load because the UT/TF/DoD server was trash.
And I'm always a sucker for Jaywalking type segments. Of which there are plenty to find on YouTube these days.
The only interview segments I can ever remember are like Norm Macdonald or whoever not giving a shit on Conan. And even for the bits only stuff like Conan going to a toy store and fucking around or whatever.
I probably have spent more hours watching The Larry Sanders Show than these inferior and higher rated competitors. Can even watch reruns of entire episodes of that.