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With over 6,000 episodes of late night talk shows behind him, David Letterman has enjoyed a TV career that few others rival. But when talking about the worst day of his life in television, Letterman doesn't bring up any of those on-air interviews or stupid pet tricks or impromptu visits to Rupert Jee's Hello Deli. Instead, he said it involved a game of catch that went frighteningly awry.
Not the answer most fans would expect, no doubt, but that's how David Letterman said it himself when appearing on The Ellen Show, even going so far as to say it may have been the worst day of his life in general. Speaking about current Ellen Show producer Mary Connelly, who also worked with Letterman during his years on NBC's Late Night, the talk show icon said the two were throwing baseballs to each other around the office when things nearly got lethal.
Mary was on one corner and 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. And down below was Sixth Avenue and the sidewalk. And you know, well, ‘How many are dead?’ I’m stunned, and so I go over to where the window is, and I’m just kind of hiding and looking down there. . . . People were looking up because shards of glass had rained down on the Avenue of Americas! I could see a guy down there, and I can hear him say, ‘Hey look, it’s Dave Letterman.’ And I go, ‘Oh, I’m spending the rest of my life in prison.’
Though he was laughing about it today and could tell the story with a smile on his face, it was pretty clear that this memory still has a way of haunting David Letterman when he thinks about it too hard. By all means, that falling baseball could have caused all manner of potentially deadly disasters. It could have smooshed someone's skull in, it could have caused traffic accidents, it could have destroyed someone's vehicle or business, and so on.
It'd be one thing if Late Night was being produced inside a high-rise building somewhere in the middle of the boonies, where the chances of striking someone hover around nil. But in New York City, in Manhattan, down Sixth Ave? As Ellen DeGeneres put it, it's something of a miracle that no one was reported injured due to that snafu. Letterman himself certainly couldn't explain how fortunate everyone was.
For this to be up there with the worst moments in his entire life, David Letterman must have truly sunken to the depths of human misery in those minutes after that baseball flew out of 30 Rockefeller Plaza that day, especially when he realized he'd been recognized. Not that any authorities would have failed to connect the baseball with the broken 14th-floor window, but still.
The point is, had the wind been a little stronger or lighter that day, some form of tragedy could have struck, and fans might never have witnessed Letterman's rise to glory at CBS' The Late Show. Fortunately, everyone survived and lived to tell the harrowing tale, and the Late Night team apparently made sure no such incident would happen again from the 14th floor. Here's what else Letterman told Ellen DeGeneres.
Mary wanted me to mention that, right after that, we had the windows covered with Lexan glass, the stuff you see at hockey games. It’s bulletproof. We had all of the windows covered with that. Problem solved.
DeGeneres laughed and mentioned that the problem could have also been solved by the Late Night peeps not throwing baseballs around like that, which Letterman also laughed at sheepishly. Not long before, DeGeneres pointed out that when she'd appeared as one of his guests in the past, Letterman had her hitting golf balls from one rooftop to another. When she admitted that those incidents could just as easily have easily gone wrong, Letterman jokingly said she would have been the one to take the blame there.
So there you have it. For all the late night talk show wars and final episodes and awkward interviews that he's experienced in the past 36 years or so of his TV career, even the death of his mother, David Letterman's worst moment involved a missed baseball that could have easily caused calamitous tragedies.
For now, though, he'll again be getting paid to interview popular celebrities for his Netflix series My Next Guest Needs No Introduction with David Letterman, which will return for Season 2 at some point in 2019. Fun fact: Letterman revealed during the interview that Ellen DeGeneres will be one of his featured guests in the second season.