Norm’s fake late gift to Conan for The Tonight Show, given after Conan was leaving, is a great example of his sort of expectation-bending humor.
His appearances on The View are legendary examples of his ability to be uncontrolled and play the dumbest guy in the room at the same time while actually being the sharpest. His intentional subversion played off as uninformed is a seemingly one of a kind talent. There are videos of interviews where he describes some of the background to things he did on the show.
“Not everything has a point” just gets me. It’s amazing how the hosts just want to jump from talking point to talking point and just refuse to let the guest actually talk, which Norm really plays off of.
And lastly, the moth joke remains a shining example of his anti-jokes.
His monologues at roasts, awards shows, and the correspondents dinner were examples of not being afraid of anything.
The other part about Norm that I'm not sure everyone knew was how compassionate and well read he was. This came out on his podcast frequently. Not only could he deliver a multi-layered joke on the fly but could casually pull references to art & literature.
I always appreciated his reverence toward his guests. Even during Jim Carrey's infamous and awkward flame-out on his show, he was never fazed or allowed it to affect his conduct towards his guests. Unless he had extra special reverence for them, in which case he might give them a harder time.
He's the only celebrity loss I can remember being brought to tears over. An absolute legend.
(If outside the US, you'll need a VPN.)
He would've won top prize on Millionaire but backed off before answering the last question from nerves.
What a legend
What's extra funny about that is that one of his The View appearances (linked above) was the day of or soon before his Millionaire appearance. One of the hosts said something along the lines of "you think he's dumb here, just wait until his appearance on Millionaire", and of course they all cackle at that. Then he goes and gives a great performance.