Remembering David Letterman’s Most Awkward Interviews

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.

Andy Kaufman — Late Night — July 28, 1982

In a lot of ways, Andy Kaufman was perfect for the world of professional wrestling. His act hinged on his audience never really knowing where the performance ended and reality began. In the early 1980s, part of his act consisted of him wrestling women, playing himself up as a chauvinist heel and declaring he was the “Inter-gender Champion of the World.” Eventually, he took his act to the wrestling hotbed of Memphis and drew the attention of hometown hero, Jerry “The King” Lawler.

The two eventually had a match against each other, which drew a lot of mainstream press coverage due to Kaufman’s role on the hit TV show Taxi. Lawler won the match with a piledriver, apparently injuring Kaufman’s neck in the process. The two would later appear on Late Night, with Dave as a sort of mediator, to settle their differences. Instead, the two got into an insult fight which then turned physical once Lawler viciously slapped the taste out of Kaufman’s mouth. On television.

Anyone who has seen Man on the Moon knows that the whole thing was, to use wrestling parlance, a “work.” Lawler and Kaufman were actually good friends behind the scenes and planned the whole scenario out. But it seems that nobody bothered to tell Dave.

Paris Hilton — The Late Show — Sept. 30, 2007

If you haven’t seen hotel heiress Paris Hilton in the news lately, well, first, consider yourself lucky. If there was ever a Babe Ruth of the “famous for being famous” crowd, it was Paris Hilton. Nowadays, she’s… apparently a DJ? Really? Anyway, before that she got famous because she was in a sex tape (yeah, thanks for starting that trend, miss) but, after that? Aw yeah! She was famous for goin’ to ja-ail! Woot! Thug life princess, y’all!

Hilton was sentenced to 45 days in jail for violating her probation, stemming from her previous arrest for the crime of being Paris Hilton in public (or a DUI, or something). Following her sentence, she made the rounds attempting to rehabilitate her public image by visiting children in Rwanda (no, seriously) and appearing on talk shows to promote her  new perfume. But all Dave wanted to do was talk about her time in custody and have a drink.

Madonna — The Late Show — March 31, 1994

For our younger readers, Madonna wasn’t always the weird lady who put her leg up on a table to get you to sign up for her music service. Or the weird lady who kissed Drake. Or the lady who, despite the fact that she’s a pop music icon, gave a sincere attempt at stand-up comedy on national TV that wasn’t terrible.

No, for a good while, she was OMG THIS WOMAN WANTS TO RUIN OUR CHILDREN AND DESTROY AMERICA MADONNA BLARRRGH. Which perfectly played on a lot of late night monologues, Dave’s included. So, when Madonna showed up on The Late Show on March 31st in 1994, the “Material Girl” (how much do you think she hates being called that by now?) wasn’t about to let Dave control the conversation and gave an interview that caused a stir with the media for weeks afterwards.

Dave kind of knew that an entertaining clusterf*ck was happening and ran with it.

Joaquin Phoenix — The Late Show — Feb. 11, 2009

After great performances in Gladiator and Signs, Joaquin Phoenix had apparently decided to ditch the movie star life and become a hip hop musician.

It turns out that it was all a ruse and part of a secret project/”documentary” he was filming with Casey Affleck that eventually became the film I’m Still Here. Both Affleck and Phoenix were looking to make a film that was a commentary on “unscripted” reality TV, and he went onto The Late Show in order to promote the film and build upon his “character.” Once the film was released and the jig was up, Phoenix returned to the show and explained exactly what the hell it was he was doing… and then later had some more fun with Dave.

Farrah Fawcett — The Late Show — June 5, 1997

It’s a little hard to write this segment on Farrah Fawcett, considering she died after a publicly fought battle with cancer in 2009. Still, before that, she held strong and starred in The Apostle with Robert Duvall and even posed for Playboy magazine in 1997. That still doesn’t change the fact that…. what in the hell was going on here?

Fawcett wasn’t the first intoxicated (or, at the very least, presumably intoxicated) celebrity to show up on The Late Show. But she certainly drew attention to herself more than most.

Crispin Glover — Late Night — July 28, 1987

Crispin Glover became — as he mentions in the video above — a “movie star” in Back to the Future, playing George McFly. We’re not sure if what he was going for in this interview with Dave was serious or just a put on but it is a sight to see. He’d go on to star with Keanu Reeves in The River’s Edge but, let’s be honest — he was a hamster pretending to be a squirrel until he played Andy Warhol in The Doors.

In this clip from Late Night, it wasn’t so much Glover’s weirdness that stands out but the fact that he wanted to show Dave that he could karate kick over his head .

In retrospect, this was actually a stunt. Glover showed up in character as “Rubin” from the yet-to-be-released film Rubin and Ed. Glover wanted this to be an “Andy Kaufman-like” prank.

Honorable Mention: Harvey Pekar

These interviews are all great displays of awkwardness, but in the above Late Night clip, Letterman and his guest, American Splendor writer Harvey Pekar, rise to someplace else. There is no veneer of politeness when Dave tells Pekar to “Shut the f*ck up. Shut up” in an effort to slow his lengthy rant about GE, NBC and Letterman’s corporate bosses. In the end, though, the only thing that could distract Pekar was an offer to play some nighttime softball. As always, even when in the midst of chaos, David Letterman knew how to find the funny.