Have a watch of this, and we’ll talk afterwards.
First of all, that Hotdog bit is great, and I want to see much more of that argument.
Let’s try and pin down when this episode aired.
The sets of shows we see are Grace Under Fire, The Larry Sanders Show (which itself wandered onto Seinfeld‘s set), Cybill, Roseanne, and of course Seinfeld.
Of those, Cybill was the last one to debut, in 1995. And The Late Show is clearly coming from Los Angeles. You’d think this would be easy to Google, but I seem to be coming up blank.
It appears to be a call back to this bit they did on Late Night in 93.
My guess is that this is from the May Sweeps in 1996 But what do I know? Maybe you do.