As David Letterman prepared to exit the late-night air in 2015 after 33 years behind the desk, EW asked his Late Night successor, Conan O’Brien, if he would be interested in writing a tribute to his hero. O’Brien wrote an insightful, moving salute to the revolutionary host, and readers weren’t the only ones who found it touching — apparently so did Letterman himself.
Letterman’s Late Show successor, Stephen Colbert, welcomed O’Brien to his show on Friday night — as O’Brien was promoting his week of broadcasts at the Apollo Theater next month — and asked him about the essay. O’Brien then unspooled a marvelous, hilarious tale about how Letterman sent him a gift at the studio lot, and it was so massive that the truck it was delivered on was having trouble getting through the gate. No, it wasn’t a vintage Porsche, as O’Brien speculated, but two cowboys in chaps unloaded an actual horse from the truck.
“Look at the expression on my face,” O’Brien said after Colbert showed a photo of him atop the horse. “That’s a man who doesn’t know what to do with a horse. Turns out, I look into it, you’ve got to feed them, you’ve got to board them, you’ve got to treat them humanely. Everyone I tell says, ‘It’s from David Letterman!’ Oh, and guess what the horse’s name is? Dave!”
After finally finding a place to board it, O’Brien decided he should try to learn how to ride the animal. “I go out to the place where I’m spending a lot of money to ride it,” he said. “I go to get on it, and they say, ‘I wouldn’t get on that horse if I were you.’ I say, Why not?’ And they say, ‘That horse is crazy.'” Turns out, the horse had thrown two people off of it, and the stable wanted him to get a letter from “an expensive horse lawyer” that will indemnify him in case the horse injures anybody.
O’Brien kept the horse for two years, with costs mounting, before his wife found a highly creative and comforting solution to the problem, which can you find out by watching the video above.