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 ...

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

It’s safe to say Donald Trump does not have a supporter in late-night legend David Letterman. In an interview with The New York Times, Letterman first reminisced—almost fondly—about what ...

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.' ...

Old footage of the president defending convicted rapist Mike Tyson has resurfaced as speculation mounts that he may pardon ...

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

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.

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

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.

Former late night host David Letterman emerged long enough from his self-imposed retirement to tackle the most-talked about topic in politics and pop culture -- Trump.

Retired late night kingpin David Letterman has a new gig on Netflix, poised to host a half dozen talk shows for the online giant — this after a previous 33-year run on NBC and CBS which yielded ...