Remembering David Letterman’s Most Awkward Interviews

05.20.15 4 years ago

CBS/Worldwide Pants

In the litany of things we’re going to miss about David Letterman, pretty high up on the list sits his legendary interviews. With a conversational style that could be politely described as acerbic, he’s frequently rubbed his guests the wrong way (Cher famously called him an “asshole” to his face, on his show). Often confused for being mean-spirited, Letterman’s interviews don’t contain the same amount of star-struck awe and pandering that often passes as a conversation in a lot of celebrity interviews.

It’s not just his strident tone that can make his interviews awkward at times. Every now and then, his guests just come across as weird, belligerent, and even downright hostile. This, of course, makes for some fantastic television.

As we watch Dave on our TV screens for the last time tonight, let’s take a look at some of the interviews that made both Late Night and The Late Show must-see viewing.

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