In a new interview with New York Magazine, David Letterman repeatedly criticizes President Trump on everything from his hair to his difficult relationship with the truth. Letterman also talked ...

Donald Trump appeared on David Letterman's show more than 30 times. The television legend now is reconsidering that legacy.

Although Donald Trump was a frequent guest on David Letterman‘s “The Late Show,” the now-retired entertainer does not have very nice things to say about the presidential candidate now. In an ...

While promoting his Netflix series, David Letterman recalls dozens of times Donald Trump appeared on the Indianapolis native's late night talk shows ...

David Letterman used to enjoy having Donald Trump on his show, back when he was just the 'boob of New York.' He's less fond of who Trump has become, a 'soulless bastard.' ...

In Letterman’s history as a talk show host, he invited Trump on his show over 30 times, where the two were very friendly with one another despite often discussing political issues.

Letterman said he ultimately thinks people need to stop focusing on every single thing Trump tweets and focus on the bigger picture. "Let's instead find ways to rebuild what is rational," he said.

David Letterman is calling Donald Trump’s presidency an “experiment” that “didn’t work,” saying the commander in chief should step down.

Now the host of Netflix's "My Next Guest Needs No Introduction," Letterman also predicts Trump will lose in a big way this week.

If David Letterman were to interview Donald Trump, he wouldn’t tussle the president’s hair. Speaking with New York magazine for a wide-ranging interview, the former Late Show host addressed ...

It's been almost two years since David Letterman delivered his last sign-off for the Late Show. But in the current political climate, it's hard not to wonder what sort of whip-smart, pointed ...