Letterman's new Netflix show opens with a clip of that final interview - which seems appropriate since Obama is the first guest on Letterman's new show. This element of chance, serendipity, I wonder if you feel that?
But the first hour of "My Next Guest" - Letterman has planned five more monthly episodes - is a frustrating exercise in talking a lot but, ultimately, saying very little.
The interview, which was about an hour long, debuts on Netflix on Friday.
This arises in connection with a filmed segment in which Letterman walks with Rep. John Lewis (D-Ga.) over the Edmund Pettus bridge in Selma, Ala., where Lewis was severely beaten in 1965 for leading a civil rights march.
My Next Guest Needs No Introduction, featuring Letterman's Obama interview, is now streaming on Netflix.
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"I have a story about Malia that I've not told anyone", Letterman tells Obama, who has his eyebrows raised in suspicion.
Letterman didn't mind the quip, either.
Addressing Letterman, Obama said, "Don't you say to yourself, 'boy, am I lucky?' I'm always surprised when I see people who have been successful and they are absolutely convinced it's because they're so smart".
Letterman, whose snow-white achievement beard has grown to Biblical proportions, shapes the episode as a love letter to the former President and his family, each member of whom he speaks of with admiration and delight. And they would just go, and they were communicating entirely through social media and we essentially built what ended up being the most effective political campaign probably in modern political history.
He is comfortable with all the talk-show shorthand: when he mentions that he and Michelle had taken a trip to the British Virgin Islands, a few enthusiastic members of the audiences hoot, and Obama gestures out in a knowing way, gently mocking that enthusiasm.
"It only had like four parts or something", Obama said. As Letterman asked Lewis how big of a setback he thinks we're enduring, a photo of the deadly "Unite the Right" rally in Charlottesville, Virginia appeared on screen-but Letterman never directly referenced it.
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"It is a major setback to the hopes, the dreams and aspirations of a people".
"Mr. President, this is what I'm struggling with at this point in my life: I have been nothing but lucky".
"Why wasn't I in Alabama?" he asks. Why wasn't I aware? On traditional televised talk series, the interviews are shorter and more promotional: politicians looking for exposure with a certain audience; actors promoting movies or, more recently, defending themselves against allegations of unsavory conduct; and, occasionally, authors hawking a book.
A brief press release from the Netflix publicity department described each episode of "My Next Guest..." as "centered around one extraordinary figure whom Dave finds fascinating".
George Clooney will be Letterman's next subject.
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He just gets it done. "I wasn't part of it a year ago , but I'm super excited to be back out there with the team", he said. That means converting third downs, eating up the play clock and running the ball down the throat of the Patriots' defense.