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Kicking off day two of the show’s “Brooklyn Week,” the retired talk show veteran of more than 30 years was greeted with a standing ovation from the audience, and joked right off the bat that “it was just good to get out of the house” and to “see famous people again.”
He explained that when he was “either fired, or retired,” (a running gag throughout his appearance) he wanted to spread the love to all the late-night talk show hosts — “even Jimmy Fallon,” he joked — by sending them gifts. As Conan O’Brien revealed on The Late Show with Stephen Colbert on Friday, he sent O’Brien a horse.
He explained the thought behind the unique gift. “The idea will be that he’ll have the horse and the horse will take a dump on the show and it will be hilarious,” he said. “So two or three days later I realize that things have gone terribly wrong,” Letterman said, explaining that he received a “lovely” letter from O’Brien saying that his wife loves the horse and will keep it. “So now I’m screwed because I was counting on him returning the horse and I would get my money back,” the former host joked.
He said he ultimately forgot the incident until O’Brien’s Late Show appearance the other day. Poking fun at O’Brien’s demeanor during the show, Letterman joked, “Now it’s like he’s losing his mind.” He continued, “From what I infer, Conan will not shut up about the horse, and something happened and the horse went crazy, maybe from being around Conan all day.”
Letterman said his ultimate takeaway is that “no good deed goes unpunished.” To which Kimmel suggests, “When in doubt, an Edible Arrangement is a good gift.”
During his Late Show appearance, O’Brien admitted that he originally believed his gift would be something much more manageable. Knowing that Letterman is notorious for being a “car guy,” O’Brien assumed that his gift could involve a vehicle. “I’m thinking he’s giving me a vintage Porsche. My mind went there. This is amazing. I’m going to have to get the crazy leather gloves,” the Conan host recalled.
After seeing he received a horse as a gift, O’Brien also found it surprising to learn the horse’s name was Dave. “The horse’s real name is Dave. He searched all over the world for a horse named Dave. Narcissism maybe?”
When O’Brien decided to embrace the gift and begin horseriding lessons, he learned the horse is “crazy.”
“Not kidding. This is 100 percent true,” O’Brien told Colbert. “They said, ‘That horse is so crazy, it’s thrown two people who have tried to ride it. If that horse is going to stay here, you have to get a legal letter drawn up by a lawyer… an expensive horse lawyer, they will indemnify you in case the horse injures anybody.’”
After realizing how “draining” his gift was and how it “cost a fortune,” O’Brien and his wife found that they could donate the horse to an Equine Massage Center, which could be considered a “Four Seasons for a horse.”
“If I was the horse, I would be suspicious thinking, ‘They’re tenderizing me.’ But no, the horse is in heaven,” O’Brien assured, adding that the horse has even fallen in love with another horse named “Charlie Rose.”
After that stressful period, O’Brien said he learned more about the late-night host than he originally knew. “I learned that Dave is a genius, but he’s an evil genius. He knew exactly what he was doing.”
On Kimmel, Letterman also talked about his new Netflix talk show. He wouldn’t divulge details — including if the show will have a studio audience or what the title will be — but did say, “We’re looking for interesting guests,” and threw Howard Stern’s name into the mix as a possibility.
The former host also poked fun at himself and his long beard, saying that the logline for tonight’s episode will read “tonight Jimmy talks to an aging vagrant.” He also reminisced on his television days. When asked if he misses it, he replied, “Some parts … no I don’t. I miss wearing makeup.”
Now that he’s retired, he said he feels like a different person. “The great struggle in life is to be better each and every day. And if you take a look around the horizon of humanity, my god, is there anything we can do, big or small, to make the life of just one person a little bit better?” he said.
On Monday night’s show, Kimmel kicked off “Brooklyn Week,” paying homage to the town in which he was born by broadcasting live from the Brooklyn Academy of Music.
To make the week more special, Kimmel enlisted help from Paul Shaffer, the former Late Show musical director and “kick at David Letterman’s side” for 33 years. In his opening monologue on Tuesday, Kimmel joked that Shaffer was the reason Letterman agreed to do the show on Tuesday. “We kidnapped Paul and said ‘you’d better show up,'” Kimmel said.
Lexy Perez contributed to this report.
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