Five of David Letterman’s Best Late Night Donald Trump Takedowns

Each time Donald Trump appeared on a late night show during his presidential campaign he often left unscathed. Stephen Colbert made a wholehearted attempt to corner Trump during a one-on-one interview in 2015, but the (alleged) billionaire dodged the host’s inquiry for an apology and surprisingly aced a pop quiz that asked if he could accurately remember his own quotes. A year later, the lone Republican candidate’s appearance on The Tonight Show caused then-ratings juggernaut Jimmy Fallon to endure massive backlash for a hair tussling incident that still seems to linger in viewers’ minds.

Trump’s talk show appearances throughout his campaign made me wish one television legend ware still working.

Nobody could tear down a guest with an inflated ego like David Letterman (see him calling Bill O’Reilly a “goon” or referring to Madonna’s hairstyle as a “swim cap”). Interviewees were often intimidated by the notion that Letterman would not throw them softballs. He wouldn’t go easy on them. If he didn’t like you, it was clear.

Trump has proven himself as a highly sensitive, thin-skinned individual (based on almost every tweet he has written since 2009). But he also has the strange ability to evade shame; where Howard Dean is solely remembered for one ill-advised yell, Trump can make thousands of inflammatory remarks and move on as if nothing happened.

In combing through the numerous times Letterman mocked Trump on both Late Night and the Late Show, it seems he came the closest to tearing down the mogul’s ego.

Letterman retired in May 2015, a month prior to Trump announcing his presidential run. But the 69-year-old has stepped out of retirement sporadically to speak out against Trump, recently discussing the Fallon incident. “I don’t want to criticize Jimmy Fallon, but I can only tell you what I would have done in that situation: I would have gone to work on Trump. But the thing about it is, you don’t have to concoct a complicated satirical premise to joke about Donald Trump.”

What would he have said to Trump? “I would have said something like, ‘Hey, nice to see you. Now, let me ask you: What gives you the right to make fun of a human who is less fortunate, physically, than you are?’ And maybe that’s where it would have ended,” Letterman said. “Because I don’t know anything about politics. I don’t know anything about trade agreements. I don’t know anything about China devaluing the yuan. But if you see somebody who’s not behaving like any other human you’ve known, that means something. They need an appointment with a psychiatrist. They need a diagnosis and they need a prescription.”

Letterman likely would not have been more than a small obstacle in Trump’s bid for the White House, but, in his own words, he “would have gone to work” on him. Trump’s previous appearances with Letterman prove that to be true. Here are five of the most memorable:

5. “You act like you’re running for something.”

When Trump appeared on Late Night 30 years ago, Letterman was incessantly inquisitive about the businessman’s financial standings. When asked what “kind of a hit” would cause Trump to “take a drink,” he said, “Hopefully, David, I wouldn’t be in a position where I’d have to take that kind of thing.” Letterman then told Trump to relax because he wasn’t running for anything. Trump is then asked by Letterman if he would run for president at some point. Trump said he doubts he would.

Another interesting quote from the interview:

Letterman: “It seems to me you are dying to get to some public platform to superimpose those feelings upon the American awareness.” Trump: “I would like to have the feelings known and let somebody else do it.”

4. Trump’s 2000 presidential run

When Trump announced his presidential candidacy in 1999, Letterman and his writers were quick to compile a list of the “Top 10 Donald Trump Campaign Slogans,” which included “He’ll give this country the same attention he gives his flimsy, poorly-constructed apartment buildings” and “Because he really needs to boost his self-esteem.”

3. “He’s just a dope.”

In 2012, Letterman said Trump’s then-criticism of Barack Obama was racist. Trump then demanded the host apologize. So Letterman went on air and addressed the issue.

“Donald Trump would come out and we would make fun of him. And he’d laugh. And we could say things about his hair…and he’d always be in his dopey red tie.” Letterman explained he called Trump a racist after Trump was insulting Obama: “I flat out called him a racist. Well, he didn’t think that was funny. So maybe it’s that he’s not a racist, maybe he’s just a guy that periodically says stupid things to get people’s attention. We could live with that because we have that in common.”

2. “This was the first time you were struck by lightning?”

Letterman showed a not-so flattering photo of Trump’s hair gone awry while in Scotland. “We got to do some wind-tunnel work on your hair,” Letterman told Trump.

Another interesting quote from this interview that seems relevant today is when Trump says, “I like to blank out negative thoughts.”

1. “The ties are made in China.”

This is the most famous incident between the two. It didn’t make much of a story when it first aired, but once Trump ran for president, Hillary Clinton was quick to highlight Trump’s contradictions.

Trump went on the show to warn Americans about China’s growing power and to promote his line of ties. Letterman asked Trump where the ties were made. Trump said he didn’t know.

Letterman is then told by someone offscreen that the ties were made in China. “The ties are made in China,” Letterman said, looking at Trump. Trump, clearly nervous, raises his eyebrows, grins, shakes his head, scrambling to defend himself.

“I’ll tell you…and you know what, David, in all fairness, I’ve been very open about that, and not all of them by the way, but I’ve been very open about that, are you okay?” Trump said while Letterman moved in his chair. “The chair is made in China.”

Some more highlights:

“I know it’s not a hairpiece, but I have no idea what it is…Sitting up close to it, it looks like the same kind of thing they did out of Mount Rushmore.”

An interesting dialogue between the two when Trump wanted Obama to be more transparent with his past:

Letterman: “Why do we want to see President Obama’s college record?” Trump: “Transparency. Does that make sense to anybody?” Letterman: “What does that mean, transparency?” Trump: “It means there’s so many hidden things that we just don’t know about out president.”

In this 2015 interview, Trump spoke with Letterman about healthcare and claimed that Obamacare was going to have a “devastating effect on the economy” in 2016. “I don’t know enough about it to say that’s not true,” Letterman said, “but I think that’s not true.” He later asked Trump if he needs “a permit for that hair.”

Five of David Letterman’s Best Late Night Donald Trump […]