1. Letterman's First Show After 9/11 (September 17, 2001)
Before the terrorist attacks on Washington and New York on September 11, 2001, we didn't think of Letterman as any sort of national spokesman. (He's too irreverent, too self-effacing, to take such a role seriously.) That changed six days after 9/11 when Dave returned to his show, still clearly stricken by what had happened. ("I remember not wanting to go back, not feeling ready to go back, but knowing we had to go back," Letterman said in 2012.) That first show remains one of his finest hours, precisely because he's struggling to find words for a tragedy that none of us could quite fathom at that moment. And yet, his extemporaneous comments captured the national mood in all its grief and bruised resolve.
Visibly trying to maintain his composure, Dave talks about dead firemen and policemen, the madness of religious zealotry, and the struggle to be courageous in the face of uncertain times. And then, he tells a beautiful story about Choteau, Montana — the same small town where he and his wife Regina would get married eight years later — that was going through a crippling economic downturn but still raised money for New York. "If that doesn't tell you everything you need to know about the spirit of the United States, then I can't help you, I'm sorry," Dave said. The night transcended great television. For a guy who tends to diminish his own achievements, Letterman delivered a broadcast the country needed.