David Letterman called Trump a 'joke of a wealthy guy' during Late Night interviews

David Letterman is one of the most outspoken comedians in late-night history. He always shared his thoughts, regardless of whether they were popular or controversial. He even went on air to talk about his own cheating scandal.

It should then come as no surprise that Letterman had strong feelings about Donald Trump. The former host of Late Night with David Letterman and Late Show with David Letterman interviewed Trump several times over the years, and he admitted that he was not terribly impressed with what he saw/heard.

David Letterman enjoyed mocking Trump on air

Letterman discussed his Trump experiences during a 2017 interview with Vulture. He felt that Trump was an essential piece of New York culture in the 80s and 90s, but not in a manner that was flattering:

"He was a joke of a wealthy guy. We didn’t take him seriously. He’d sit down, and I would just start making fun of him... He was big and doughy, and you could beat him up."

The legendary talk show host conceded that Donald Trump was a good sport, and the audience seemed to enjoy jokes being made at his expense. The customer, as they say, is always right, and Letterman was keenly aware of this dynamic. "He never had any response," Letterman recalled. "He seemed to have a good time, and the audience loved it, and that was Donald Trump."

Letterman repeatedly targeted Trump's hair

One of the most intriguing revelations in the Vulture interview, however, came about when David Letterman relayed a comment he heard from a PR manager. The manager told him that Trump would never consider running for president. "He was just monkeying around for the publicity," Letterman was told. This obviously proved to be false.

Letterman has voiced his stern opposition to Donald Trump as a politician, but he also took the chance to throw a few jokes his way during this 2017 discussion. The thing he couldn't seem to get over was Trump's hair. "I mean, we elected a guy with that hair," he quipped. "Why don’t we investigate that?"

Letterman is currently hosting My Next Guess Needs No Introduction on Netflix.