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

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 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 ...

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 ...

Thanks to Donald Trump, David Letterman has come out of retirement. Less than two months after he left CBS' The Late Show, Letterman appeared onstage in San Antonio, Texas, Friday with Steve ...

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.

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.

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 ...