Why Letterman is the real King

Because he does "irony" and eviscerating self-mockery better than anyone ever has:

Cold open: We see Dave sitting with our old friend Jude . Dave attempts to make conversation.
Dave: "Big plans for the 4th?"
Jude: "No."
Dave: "I was thinking maybe you might want to come over and we could grill up some burgers."
Jude: (beat) "We're not friends. I don't like you. You use money and fame to bully those around you. You're actually the most unlikable person it's ever been my misfortune to know."
Dave: (beat) "If you don't want to do burgers, we could maybe go see a movie."

And, of course, he does this: