Dave Letterman Worried His ‘Late Night’ Shenanigans Might Have Killed Someone

“Honest to God, it was the worst day of my television life,” David Letterman told Ellen DeGeneres back in 2019, as reported by Last Night On. “And maybe the worst day of my life.”

Good gravy, Dave, what happened? A Top Ten list that only went to seven? Larry “Bud” Melman got run over by the D train? An intern outing a Letterman affair on national television? 

Somehow it was worse than all that. Letterman was horsing around with his producer, Mary, both wearing baseball mitts and whipping hardballs around the office. “Mary can bring it, there’s no question about that,” remembered the comic. “And we’re trying to get that thwack, just that perfect thwack you get when the ball hits the pocket.”

Producer Mary was in one corner of the office and Letterman was on the other, heaving the ball back and forth as fast and hard as they could. Then “one got away from me,” explained Letterman. “It went up and over and through the window of the 14th floor of the 30 Rock building. And down below was Sixth Avenue — and the sidewalk.”

Letterman’s horrified reaction? “Well, you know,” he said. “How many are dead?”

The line got a laugh but Letterman wasn’t joking. A regulation baseball dropped from 14 stories up could do some serious damage to a passerby’s skull. A baseball that was thrown as hard as Letterman could? Not to mention the falling fragments of razor-sharp glass? 2019 Letterman looked ashen as he remembered the scene. “I’m stunned,” he told DeGeneres. “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 to speak of.”

Mary, now working as one of Ellen’s producers, corrected him. “Well,” she said, “people were looking up.”

“People were looking up because shards of glass had rained down on the Avenue of the Americas,” Letterman said.  

One of those people supposedly looked up and pointed. “Hey, look, there’s Dave Letterman!” 

That sealed it for the Late Night host. “I go, ‘Oh! I’m spending the rest of my life in prison.’”

The fact that Letterman was telling the story on a talk show years later lets you know that, thankfully, no one was maimed by the plummeting objects. “It’s a miracle no one got hurt,” DeGeneres marveled, remembering one of her own experiences on Letterman’s old show when she whacked a golf ball from the roof of one Manhattan building onto another. “That also could have gone badly,” she realized.

That was different, said Letterman, because “that would’ve been on you.”

Each situation resulted in zero casualties, and Letterman appeared grateful that good luck had intervened. He asked DeGeneres what she would do if she was in a similar situation. She didn’t quite know how to respond: “Back up slowly?” she stammered. 

“No, no, no,” Letterman said, speaking from experience. “You send an intern down there.”