David Letterman Thinks He Stayed on Television Too Long, Reveals What He'd Ask Trump Today

The “My Next Guest Needs No Introduction” star shares the moment he thought he might go to prison forever, and his most rebellious act in Ellen’s “Burning Questions.”

Ellen DeGeneres was thrilled to have David Letterman as her guest on Thursday, but the former late-night host admitted he was incredibly uncomfortable in the guest’s seat after 30 years behind the desk.

Nevertheless, he proved an amiable and charming guest. He also proved that he’s learned a lot in the four years since he stepped away from CBS’s "Late Show" and reflected on his life. One of the first things he learned after stepping back and taking stock was that he’d simply stayed on the air way too long.

Ellen tried to argue with him. "That’s not true," she said, but he shut her down immediately.

"Yes it is true, and I’ll tell you what happened," David said. "It turns out nobody had the guts to fire me. And I should have left like ten years ago. You want to make sure you have some energy to direct toward other things."

He went on to praise Ellen’s ability to do her talk show and all the other things that are important to her, like her charity work. He said he was just way too concerned with himself, "looking at the telescope through the wrong end."

Now, though, David has found the time to give back through Habitat for Humanity, even as he has a new talk show on Netflix, "My Next Guest Needs No Introduction." He teased Ellen’s audience that he had scored her as a guest for its upcoming second season.

It was through Habitat for Humanity that Ellen was able to convince David to play her favorite game, "Burning Questions," by bribing him with $1,000 toward the charity for every honest answer he gives.

"Now let me ask you about this; am I going to look stupid?" David asked her about the game.

"If it goes right, yes. That is our intention."

Resigned, David said softly, "Alright."

To his credit, though, David actually came across as very forthright, humble and honest. He spoke about his first love and a fatherly connection he had toward his first employer when he bagged groceries in high school. He also revealed his most rebellious moment as a teenager, and something truly disgusting that he loves and everyone else hates.

Seriously, David Letterman makes sandwiches that are so gross, we can’t even bring ourselves to write it here. You’ll just have to watch through the end of the above video and see if you can avoid making the same grossed out face Ellen does.

She also asked him what he might like to ask President Trump if he had the opportunity to interview him again. "I knew President Trump," David said seriously. "I’m disappointed in his administration."

After a few moments of thought, he finally answered. "I would say to him, Don, why are you such a putz?"

Elsewhere in the show, David confessed to the moment he thought might be the end of his career. And it all started innocently enough when one of Ellen’s executive producers used to work for him and they would toss a baseball back and forth.

"Mary was on one corner, I was on the other corner, and one got away from me and it went up and over and through the window of the 14th floor of the 30 Rock building," David said. "And down below was 6th Avenue and the sidewalk."

Mary, who was on set producing Ellen’s show, reminded him that people were looking up. "People were looking up because shards of glass had rained down on the Avenue of Americas," David recalled. "And I see a guy down there and I hear, ‘Hey look, it’s Dave Letterman,’ and I thought, oh, I’m spending the rest of my life in prison."

Perhaps even more remarkably, absolutely no one was injured from either the baseball or the broken glass. And perhaps someone out there has one hell of a souvenir and they think it’s just a baseball they found on the street.

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