Trump has a long history with the retired late-night host, and was frequently a guest of Letterman’s going back to the 1980s.
The pair’s relationship was more amicable back then.
As Letterman put it in his most recent interview, “Nobody took him seriously, and people loved him when he would come on the show. I would make fun of his hair, I would call him a slumlord, I would make fun of his ties. And he could take a punch like nothing. He was the perfect guest.”
Trump’s most famous — and possibly most damaging — appearance on the show was probably in 2012, when Letterman grilled him over the outsourcing of his clothing line. Trump admitted he didn’t know where the clothes — sold at Macy’s — were made, offering “someplace” as a location before Letterman revealed the shirts and ties were made in Bangladesh and China.
The interview was repurposed by Hillary Clinton’s campaign in an ad that blasted Trump for the outsourcing. “I was pleased,” Letterman told the Times of the ad. “I felt like I still have a small voice in this. I thought it was good.”
In another interview from 2008, Trump discussed flipping a house to Russian “fertilizer king” Dmitry Rybolovlev. His evolving politics are interesting to watch; at one point he earns applause from the studio audience for criticizing the government’s military spending while “cities like New Orleans are dying.”
In another interview from 2010, Letterman asks Trump what he “fixed” about the Miss America pageant. “I made the heels higher and the bathing suits smaller,” Trump said.
“With this kind of genius, we have nothing to worry about,” Letterman responded dryly. “Everything is going to be fine.”