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Great Moments in David Letterman interviews

We all know now that Feb. 11 was a blur for Joaquin Phoenix, and Feb. 12 turned out to be a blurry cold/flu vision for me, but who will look at this Friday the 13th and find it blurry? Spoiler alert: Probably you. That said, the Phoenix interview on The Late Show with David Letterman got me thinking about Letterman's many great and infamous moments over the years. There are a few people who look upon their Letterman spots as times to shine, whether it be for good (Bill Murray, Martin Short, Bruce Willis) or those who use him for their own evil self-purposes (Bill O'Reilly, Howard Stern, Paris Hilton). And then there are those who, well, just sort of take over the show, whether they meant to or not. This blog post is devoted to those celebs who took Letterman by surprise before Joaquin Phoenix.

The nine greatest moments in David Letterman interviews, after the jump.


1) Farah Fawcett. Let's start with Fawcett, because Letterman name-checked her near the end of his chat with Phoenix. She appeared on the show in 1997 to promote her Playboy pictorial and a new DVD that also showed how well she had aged. Only problem was, she couldn't make any sense out of anything.

2) Andy Kaufman. When people talk about hoaxes, this is the first thing that comes to mind, as Kaufman brought his "feud" with professional wrestler Jerry Lawler into network late-night TV. This is re-created as part of the Kaufman biopic, Man on the Moon. It really seems as though Dave has no idea what's going on here.

3) Madonna. I remember hearing about this one for more than a 24-hour blog cycle, as people talked about all of the profanity Madonna uttered, and how awkward it all got for Dave. Although watching it again now, it almost seems as though he started it with his intro. Don't you think?

4) Courtney Love. Oh, how she tried to duplicate the funny surprise that Drew Barrymore presented for Letterman's birthday, except everything goes terribly wrong. She wants to blame it all on the FCC, but really, the blame is on her.

5) Harvey Pekar. This was from his final appearance. Letterman banned him after this final conflict.

6) Cher. It's 1986, and she explains she has not been on the program because she hates Letterman. No, wait. She likes him, but merely thinks he is an a-hole. Talk about awkward. It does get better, though.

7) Crispin Glover. This is the other totally weird performance that Letterman could not figure out at the time, and he cited Glover first (and then Cher) as his most frequently asked guest during his NBC era.

8) Richard Simmons. This is from what could be his final appearance, as Dave and the crew apparently decided they had had enough of his antics and wanted to punk him once and for all.

9) Michael Richards. The only thing weirder than Michael Richards freaking out at a heckler in Los Angeles was his haphazard apology to Letterman, via satellite, with Jerry Seinfeld on the set. Who said this was a good idea, again?

Sean L. McCarthy

Editor and publisher since 2007, when he was named New York's Funniest Reporter. Former newspaper reporter at the New York Daily News, Boston Herald and smaller dailies and community papers across America. Loves comedy so much he founded this site.

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20 thoughts on “Great Moments in David Letterman interviews

  1. These are some good choices for this topic. But not all.
    The Fawcett thing, I think was legit. Something was wrong with her.
    Glover has always been that screwy, but I don’t think Letterman knew he was going to be quite that disruptive that day.
    The Richards thing is another deal entirely. There was not lose of control opf the interview, but it was odd to have him on during the Seinfield segment, and I like everybody else, thought it was a joke at first.
    Richard Simmons is not being banned, no way. They may have messed with him, but the staff always knows that’s how it will be when he comes on, and they play that up.
    Kaufmen and Lawler was the worst choice. It made for a wild TV segment, but it was staged from the first moment. Everything Kaufman did was “a happening”, or fake. Even Lawler was always in on these acts, as we have learned.

  2. Don’t know how you can include the Courtney Love appearance without including the original Drew Barrymore appearnce that inspired it. The genuine shock on Dave’s face and Drew’s impish glee just made this one of the most hilarious talk show bits I have ever seen

  3. Don’t know how you can overlook the night Julia Roberts was so overtly flirtatious that she finally pressured Letterman into making out with her. (Not quite as hilarious as Stephen Colbert losing all control when Jane Fonda sat on his lap and nibbled his ear, but still pretty amusing and — yeah, I’ll say it — heartwarming.)

  4. This is a list of the biggest screwball moments when the show went off the rails, which is why Drew Barrymore’s birthday surprise is not on there but Courtney Love’s copycat disaster is. Same for Julia Roberts, I suppose.
    When Letterman was making the move to CBS, he spent one of his final NBC shows talking about the guests everyone always asked him about. Back then (1993), he said people wanted to know more about the Crispin Glover and Cher chats. I completely forgot about that Oliver Reed one, which also is quite odd, eh?
    The Kaufman-Lawler episode was so infamous it had to be included, especially since as many people argue, Letterman may have known as much about this incident beforehand as he did this week’s Joaquin Phoenix episode.

  5. Possible to comment without account?
    For me the most bizarre Letterman moment was Fred Williard’s appearance winter 1987-1988 promoting D.C. Follies with an apparent mix-up of the promo tape leading to the airing of a BDSM session of Williard and a dominatrix. Anybody remember this?

  6. a few more i think should be considered…
    how about with don king?
    king’s just going on and on and on about this and that. dave can’t break in to the torrent of words spewing out of king’s mouth.
    finally, finally, king stops long enough for dave to ask: “don, what’s the deal with the hair?”
    pandemonium…
    and then there’s the time nastassia kinski came out with some ludicrous hairstyle – just wierd. but dave couldn’t do anything with it…
    and then in the early nineties, after julia roberts hit it big – she had been on the show a few times before ‘pretty woman’ – it comes out that she had called dave to ask him to perhaps be her escort to a movie opening some time prior. as she describes it, turns out that she had called the show and asked mortie to ask dave. but at that time, she wasn’t that big so mortie didn’t pass along the message. and now that julia’s huge, dave’s looking at mortie like ‘wtf?!’
    this all comes out during the show (maybe not actually true) but it was great tv…
    i’ll never forget crispin glover but those are special moments for me…

  7. Nowhere near the level of any of these, but I remember Tia Carrere was Letterman and made a big “WOO! I’m ON DAVID LETTERMAN!” type gesture, and I always remember Daves utterly digusted face…
    The Gene Shallott (sp?) interview isn’t on Youtube either…

  8. Richard Simmons has been on once or twice more since the exploding steamer. The better interview–and the one that actually did get him “banned” for several years–was the Thanksgiving turkey episode where he climbed on Letterman’s desk and Letterman chased him off the stage with a fire extinguisher while hurling obscenities at him. The exploding steamer clip was his first visit back after several years.

  9. Richard Simmons has been on once or twice more since the exploding steamer. The better interview–and the one that actually did get him “banned” for several years–was the Thanksgiving turkey episode where he climbed on Letterman’s desk and Letterman chased him off the stage with a fire extinguisher while hurling obscenities at him. The exploding steamer clip was his first visit back after several years.

  10. Richard Simmons has been on once or twice more since the exploding steamer. The better interview–and the one that actually did get him “banned” for several years–was the Thanksgiving turkey episode where he climbed on Letterman’s desk and Letterman chased him off the stage with a fire extinguisher while hurling obscenities at him. The exploding steamer clip was his first visit back after several years.

  11. Richard Simmons has been on once or twice more since the exploding steamer. The better interview–and the one that actually did get him “banned” for several years–was the Thanksgiving turkey episode where he climbed on Letterman’s desk and Letterman chased him off the stage with a fire extinguisher while hurling obscenities at him. The exploding steamer clip was his first visit back after several years.

  12. You lumped in Howard Stern with O’Reilly and Paris Hilton? You clearly don’t know anything about comedy sir.
    Stern and Letterman have a great fondness and respect for one another. Stern is the most coveted guest on Letterman every year.

  13. Yeah, they’re all right on target. Poor Farah. We didn’t love her enough…
    Too bad he never had you & Bobby Pappas on as guests. One good “Sugarman” take & you probably would have had Dave rolling.

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