O'Brien illustrated this idea through the lineage of late-night comedy: Jack Benny was the greatest of his generation. Johnny Carson wanted to be Jack Benny but wasn't, and his failure to become his hero made him the funniest person of the next generation. David Letterman wanted to be Carson and wasn't. O'Brien's generation wanted to be Letterman and missed that mark in a thousand different ways. The point, he said, was that deviating from the expected path — even painfully — can become the catalyst for profound reinvention.