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“It’s so nice to be around famous people again,” Letterman joked after he thanked DeGeneres for having him on the show.
The legendary late night host shared that on the way to the daytime talk show’s taping, he was stopped next to a bus that takes tourists to celebrity homes. “I think, ‘This is gonna be great. I’ll roll down the window, because I used to be a celebrity, and I’ll start screaming at these people,'” he said.
Unfortunately for Letterman, he did not receive the response he expected. “There’s no glint of recognition,” he said. “They have no idea who I am.”
Letterman admitted that he was uncomfortable being the guest of the show as opposed to the host. “I used to do what you do, and now I’m doing what other people do,” he said.
He updated viewers on how his 15-year-old son, Harry, is. While he shared that his son’s voice used to be so high-pitched that he sounded like a member of an “Austrian’s boy choir,” it has dropped many octaves.
Letterman added that Harry has no interest in spending time with him and cited his “behavior” as the problem.
While Harry told his father not to talk about him during the show, that didn’t stop Letterman from telling a story about taking a trip to Easter Island for an assignment when he was in fourth grade.
Letterman shared that a drunk man was at a restaurant on the island. “My son is horrified,” he recalled. The drunk man scared Harry so much that he got up and ran back to their hotel room.
About one month after the trip, Harry’s teacher called to tell Letterman that his son’s paper about the trip mentioned that the drunk man chased him out of the restaurant. When he told the teacher that was true, she responded, “Oh OK, ’cause that’s all he really mentioned in the paper.”
Letterman’s appearance also served as a reunion with former Late Show producer Mary Connelly, who currently serves as an executive producer on Ellen.
He shared a story that began with him and Connelly playing catch inside 30 Rockefeller Plaza in New York City. “We’re trying to get that thwack — just that perfect thwack you get when the ball hits the pocket,” he explained.
The ball “got away” from Letterman and broke through a window on the 14th floor and landed outside on 6th Avenue. He admitted that his first thought was, “How many are dead?”
“So I go over to where the window is, and I’m just kind of hiding and looking down there, and there wasn’t really any commotion,” he said, though Connelly said that people outside were looking up at the window. “Shards of glass had rained down on the Avenue of the Americas.”
When he heard one pedestrian announce that he saw Letterman, he thought, “I’m spending the rest of my life in prison.”
Letterman said they soon fixed the problem by covering the windows with Lexan glass, which he said was “bulletproof.”
While Letterman currently hosts the Netflix series My Next Guest Needs No Introduction, he said that he overstayed his welcome as a television host.
“Here’s the mistake I made: I stayed on television way too long,” he said. “It turns out that nobody had the guts to fire me, and I should’ve left 10 years ago. You want to make sure you have some energy to direct toward other things.”
He admitted that he had to pick up other hobbies when he left The Late Show. “There’s more to life than ‘So tell me about your pet beaver,'” Letterman said. He added that his current work with Habitat for Humanity now keeps him busy when he’s not filming the Netflix show.
Letterman’s appearance concluded with a game of “Burning Questions.”
During the segment, Letterman revealed who his first crush was, the most rebellious thing he did as a teenager, his favorite body part to look at in the mirror and a lie that he recently told.
He also disclosed that his favorite non-show-business job was working at the Atlas Supermarket, where he and his friends regularly stole beer. Letterman then admitted the one thing that drives his family crazy is that he is always trying to get his son to dance, even though he is not a good dancer.
DeGeneres then asked Letterman what he would ask Donald Trump in an interview.
“I’m disappointed in his administration,” he began. “I would say to him, ‘Don, why are you such a putz?'”
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William Jackson Harper
Friends: The Reunion