David Letterman may not be the greatest late night host ever (sorry, nobody’s ever going to top Craig Ferguson), but there’s one type of interaction in which Letterman absolutely shines: dealing with people he has no respect for. If Letterman thinks the guest isn’t worth his time (and he’ll let you know within the first thirty seconds), you’d be well advised to set the Tivo and microwave a bowl of popcorn, because shit is about to get hilariously awkward.
I used to think it was his becoming old, crotchety and possibly senile that gave rise to this bizarre streak of gut-busting faux pax, but the videos gathered below prove without a doubt that Letterman’s been a dismissive prick since the very beginning. Well played, sir.
The Guest: Simmons isn’t the kind of guy who demands a lot of respect to begin with. It’s like how in nature, animals sometimes display bright colors as a warning that they’re dangerous. But, you know, the opposite.
The Tipping Point: At the beginning, you can almost tell yourself Dave’s genuinely faking interest. Sure there’s some sort of dangling tray fouling up the segment, but he’s not about to let that ruffle him. Unfortunately Simmons use of the phrase “go-go kart” is an offense he apparently can’t let slide by without comment.
The Highlights:
The Guest: I think I summed up my thoughts on Bill O’Reilly fairly well by spending a week making a five-minute video of him being an irresponsible prick. Dave’s feelings are probably along the same lines, which meant this clip was destined for Youtube greatness.
The Tipping Point: After Dave spends a good thirty seconds thoughtfully articulating his fairly complex standpoint in response to Bill’s browbeating, emotionally provocative, sound bite of a question, Bill interrupts him to repeat the same question, but louder. It’s at this point you can see Dave realizing that they are no longer in the realm of reasoned debate, and responding accordingly.
The Highlights:
The Guest: As you may recall, Michael Richards went on an ethnically-themed tirade at a comedy club in the mid-00’s. In case watching the video of that wasn’t uncomfortable enough for you, here he is stammering out an awkward apology on national television.
The Tipping Point: This one’s not Dave acting disrespectful as much as the whole damned situation being as uncomfortable as a long car ride with the grandparent who’s “of a different era.” Still, the fact that Dave calls Richards out when he seems to blame the black guys in the audience because they “heckled him” lets you know he’s not a big Kramer fan.
The Highlights:
The Guest: On some level, Paris Hilton must be aware that society by and large considers her an imbecile. It’s what she’s built her empire on. That, and her weird half-closed left eye. So it’s in keeping with her nature that of all the nights she could have appeared on The Late Show, she chose the week after she was released from prison. Thanks to Dave, she’s not likely to make that mistake again.
The Tipping Point: Letterman clearly had this ambush planned from the very beginning. Basically the first words out of his mouth are “so…prison.” From about 0:50 on, it’s just a long tragic slide into a lecture from your Dad.
The Highlights:
The Guest: A lot more press was made by McCain’s failure to appear on The Late Show than when he actually did show up, but there’s not a lot more awkward than watching him trying to explain himself to several million swing voters while being openly mocked.
The Tipping Point: When McCain is forced to utter the three words that can kill a Presidential campaign—“I screwed up”—and Dave laughs the laugh of a man who just warped the course of American history with his stupid TV show and unwillingness to let anything go.
The Highlights:
The Guest: Harmony Korine is the heroin-chic avant garde writer/director who helped bring us Kids and Gummo, two mock-documentaries about how terrible stuff can be if you’re poor, HIV-positive, addicted to drugs, or just leading a miserable, fucked up life. I know what you’re thinking: laughs ahoy!
The Tipping Point: Dave’s description of Harmony as “pleasantly odd” doesn’t exactly set the bar very high, but when he sees the way Korine is dressed and asks if the “skate park was closed,” you know Dave’s officially shifted into crotchety old man mode and is fixin’ to drive us all the way to Awkwards-ville at eight miles an hour with the blinker on.
The Highlights:
The Guest: Robert Crumb collaborator and central character of the film American Splendor, Harvey Pekar here manages to somehow be uglier and more obnoxious than Paul Giamatti putting all of his considerable talents towards being ugly and obnoxious.
The Tipping Point: It’s pretty apparent from Harvey’s other appearances on the show that Letterman’s Producers booked him for the sole purpose of causing a TV train wreck that channel surfers would be forced to stop an ogle. So when Letterman literally bans Harvey from the show, he’s essentially saying “hosting my own show is not worth the ordeal of talking to this man for four minutes.”
The Highlights:
The Guest: Before cowgirl Madonna, Kaballah Madonna, and Guy Ritchie-ruining Madonna, there was filthy sex goddess Madonna. Here, she punishes Dave for making jokes about her promiscuity and unseemly nature by graphically detailing her sex life and cursing like a sailor.
The Tipping Point: Really, it’s Dave’s fault. He just had to push her. And after he spends the opening minute of the interview trying to get Madonna to kiss an audience member, she signals the beginning of his penance by calling him “a sick fuck.” From the look on Dave’s face, he knows things are only going to get worse from there.
The Highlights:
The Guest: Twenty years later, debate still rages in the lamer corners of the Internet as to whether this is footage of Crispin Glover, world’s best actor, or Crispin Glover, world’s highest man. Fake or real, it’s worth watching if only to see Paul Shaffer with slightly more hair.
The Tipping Point: Whatever tipping point preceded this display of drug-induced self-reproach and pale nerdy flexing happened long before the interview took place. My question is how they did a rehearsal interview without realizing the guy was on a mountain of angel dust big enough to have been the remains of a wildfire in heaven.
The Highlights:
When not collecting moments we’d rather forget, Michael is head writer for and co-founder of Those Aren’t Muskets!
This entry was posted on Monday, January 26th, 2009 at 8:00 am and is filed under Uncategorized. You can follow any responses to this entry through the RSS 2.0 feed. You can leave a response, or trackback from your own site.
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November 13th, 2009 at 3:06 am
FYI, when Madonna claims that “untrue rumors” is an oxymoron, she is using the term correctly, asserting that rumors are generally untrue, contrary to what the writer states (”Madonna calls ‘untrue rumor’ an oxymoron which implies that she believes all rumors to be true”). An oxymoron is a claim of redundancy, meaning the two words have the same meaning, she is stating the opposite of what the writer claims.
November 12th, 2009 at 9:36 am
He may also be high, but the outfit and the personality are a character from the movie Rubin and Ed, where Crispin Glover helps a used car salesman bury his dead cat.
October 1st, 2009 at 2:38 pm
Haven’t actually read the list yet, too busy being embarrasingly happy that someone else recognize the genius that is Craig Ferguson =)
August 30th, 2009 at 4:36 am
Kudos for mentioning Craig Ferguson!!
Also great article!
August 27th, 2009 at 11:22 pm
I spent so much time watching the entire Madonna segment I don’t remember anything previous, but the Crispin segment was clearly just a staged thing. No less funny for that, since most of these seem to be staged while still hilarious.
August 10th, 2009 at 7:17 am
You should extend this list to 10 and add the Joaquin Phoenix interview.
August 3rd, 2009 at 7:40 am
Craig Ferguson, number 1 ? You gotta be kidding! I can’t even watch him. Johnny Carson will ALWAYS be number 1, followed by Letterman and Leno.
July 5th, 2009 at 5:16 am
Dave may be a dick, but he’s the funniest dicks I can think of. I’m not saying I think about dicks or anything. Certainly not while I watch a 60+ year-old tell jokes. I never think of dicks. Ever.
I’m not gay.
July 4th, 2009 at 11:23 am
[...] are now the 34th most popular awkward anything on the web, right behind Cracked.com’s list of David Letterman’s most awkward moments. I am so filled with joy right now that I’m literally peeing tears. Or, whatever it is that [...]
June 8th, 2009 at 11:55 pm
That’s an interesting article. I just wondered if you could tell me where to find more info on this topic ?
June 5th, 2009 at 11:08 am
I think Harmony took at least 10 bong hits before coming on.
May 31st, 2009 at 1:08 am
Awwwww no Andy Kaufman
May 26th, 2009 at 5:48 pm
Thanks for a lovely site, I am very impressed
May 5th, 2009 at 2:25 am
Crispin Glover was actualy doing that interview in character from his upcoming movie Rubin and Ed hilariously that film wasn’t released until 1991 so most people forgot about this interview and chalked it up to him being the craziest fucking guy on the planet.
April 25th, 2009 at 5:44 am
DECLARATION ESSENCE by Cartier
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March 15th, 2009 at 1:58 am
I think it should be apparent to everyone that Harmony Korine is really, really high.
February 23rd, 2009 at 9:05 pm
heh my sentiments have been echoed many-a-time already. edit the post and add joaquin!
February 22nd, 2009 at 11:02 pm
Harvey Pekar, truly madly, deeply, a First Class Turd!
February 22nd, 2009 at 4:56 pm
Ya true. The joaquin interview definitely needs to be added to this list.
February 22nd, 2009 at 12:15 pm
Too bad this article came out only a couple weeks before Letterman’s hilariously awkward interview with “Joaquin Phoenix”
February 21st, 2009 at 2:49 am
So there’s been four count’em FOUR ripoffs of this exact article in just the past week.
http://www.popeater.com/television/article/best-moments-david-letterman/341452
http://tv.yahoo.com/blog/david-lettermans-top-ten-most-insane-interview-moments–130
http://www.time.com/time/specials/packages/0,28757,1879231,00.html
And oddly enough, none of the new clips they added to try to hide the fact that they’re ripping this off, are anywhere near as funny as the stuff here. Although Joaquin Phoenix’s interview comes very very close and would have made a wonderful tenth addition to this article.
February 20th, 2009 at 12:41 pm
I just wanted to thank you for giving Craig Ferguson the love he deserves. I adore him and his stand up routine for the NY comedy festival it was one of the funniest hour 1/2’s of my life. Dave is great, but Craig is my not-so-secret older man crush (I am in my mid twenties) and it makes me happy when people prefer him to Conan.
February 19th, 2009 at 7:47 pm
Okay, in the Harmony Korine bit the best part by far is, “This, by the way, is why they invented child-proof caps.”
February 19th, 2009 at 4:19 pm
The Letterman/Hilton clip was taken down. Here’s another one: http://www.youtube.com/watch?v=HdpO57nz3Rc
February 17th, 2009 at 1:27 pm
Harmony is playing Dave here not the other way around, wake up
February 16th, 2009 at 12:33 pm
Dude, it’s no secret that Letterman is a curmudgeon. Is it his fault if Joaquin Phoenix is dressed like Rick Rubin, or Crispin Glover is baked out of his mind? No, of course not. You’re missing the whole point of Dave’s show. Would you like to sit there and watch a Charlie Rose-like show every single night? Is Dave supposed to escort a fucking guest out the second something awkward happens? No. If you hate Letterman so much, watch Leno give the cookie-cutter interviews that a blind monkey could give. If the guests don’t want to get ripped by Dave, they shouldn’t be crazy, stoned a-holes to begin with.
February 15th, 2009 at 11:31 pm
Letterman is a boring assclown
February 15th, 2009 at 5:44 pm
Man, the followup interview two years later for Crispin Glover is just as bad. . . He clearly doesn’t want to talk about trying to do some kind of karate kick. . . it’s pretty funny. Especially when Dave says, “When you get your own show, you can set the agenda.”
February 15th, 2009 at 2:49 pm
Another lazy author copying from cracked:
http://www.popeater.com/television/article/best-moments-david-letterman/341452
Don’t tell DOB. Remember what he did to the Mexicans?
February 15th, 2009 at 7:16 am
Everybody’s doing the Swaim!! another top ten letterman list:
http://tv.yahoo.com/blog/david-lettermans-top-ten-most-insane-interview-moments–130
February 14th, 2009 at 11:10 pm
I almost forgot Farah Fawcett. Dave was none too kind that night. And he made reference to it during the Joaquin Phoenix interview. He apologized to her
February 14th, 2009 at 11:08 pm
Go look at his interview with Natasha Kinski and tell me it does not belong in a top 9 or 10. And don’t forget Shirley McLaine. Those deserve to be on the list.
February 14th, 2009 at 6:02 pm
agree, kudos to the originator. Farking Time magazine rip-off.
February 14th, 2009 at 3:38 pm
damn everybody found out about the time article before i did
February 14th, 2009 at 11:19 am
I just read the Time article as well. Your article was better.
http://www.time.com/time/specials/packages/0,28757,1879231,00.html
February 14th, 2009 at 9:03 am
Hey Swaim, Time is totally ripping you off:
http://tinyurl.com/ch32ax
February 13th, 2009 at 10:45 pm
Man, what a dick.
February 13th, 2009 at 10:22 pm
And then there was whatever-the-hell Phoenix. WOW! What a waste of air time, and then Dave aced it by saying he owed Farah Fawcett an apology. Yeah, her and everybody that endured that 6 weeks in ten minutes.
February 13th, 2009 at 5:36 pm
[...] as “Nancy Grace” and “The View,” has compiled what they claim as “Letterman’s 9 Most Hilariously Awkward Moments.” (Tip of the hat to [...]
February 13th, 2009 at 4:14 pm
All are great, but I’d also include the Mr T/Wrestlemania interview from the mid ’80s. Truly a classic!
February 13th, 2009 at 2:09 pm
You left out the Drew Barrymore dancing on the desk, flashing Dave segment! Come on now…
February 13th, 2009 at 12:40 pm
@ Rufus
I’m not saying O’Reilly’s not an A-Hole, I’m just saying that I don’t agree with the assessment that Letterman was a hero here.
“Have someone try that on his own show and you’ll get the standard “Cut his mic!” from ‘tough-guy’ O’Reilly.”
I’ve seen O’Reilly’s show several times (thought not that often), and I’ve never seen him do that (I’m sure it’s happened, but I don’t think it’s “standard” as you try to make it sound). I think you’re thinking of Sean Hannity.
He actually is surprisingly civil to the guests I’ve seen him with (except Barney Frank, but he had it coming IMO). But, he does call them out when they try to avoid questions.
“But you are right - he doesn’t like people dancing around questions. That’s why he kept badgering Andrea Mackris with inappropriate sexual requests when she wouldn’t just hang up on his perverted ass.”
Emotional and off-topic. Again, I’m not saying he’s not a jerk personally. In fact, I’m quite sure I wouldn’t get along with him if I met him.
But as a commentator, he’s actually pretty fair (you don’t see that often because people only post clips where he gets worked up), the times I’ve watched it he often gives people the last word even if he disagrees with them.
February 13th, 2009 at 9:54 am
@ joe schmoe:
“he doesn’t take it when people dance around questions”
No, O’Reilly behaves like that because he’s just a bully. He’s on someone else’s show, and acts like an asshole because that’s his schtick.
Have someone try that on his own show and you’ll get the standard “Cut his mic!” from ‘tough-guy’ O’Reilly.
But you are right - he doesn’t like people dancing around questions. That’s why he kept badgering Andrea Mackris with inappropriate sexual requests when she wouldn’t just hang up on his perverted ass.
February 12th, 2009 at 6:22 pm
“After Dave spends a good thirty seconds thoughtfully articulating his fairly complex standpoint in response to Bill’s browbeating, emotionally provocative, sound bite of a question, Bill interrupts him to repeat the same question, but louder…”
You mean after Dave spent thirty seconds avoiding the question. It wasn’t a “complex standpoint”. He was explaining why he originally thought it might have been good to go into Iraq, and then later changed his mind (like all Americans apparently). But that’s not what the question was about. The question was “Do you want us to win in Iraq?”, i.e., given the fact we’re already there and the options are to bail out or stay the course. It was a simple question, and Dave’s only recourse at being called down was to try to look intellectually/morally superior with “it’s not easy for me because I’m thoughtful.”
That’s why O’Reilly repeated it, and then again even louder, because he doesn’t take it when people dance around questions.
February 12th, 2009 at 6:16 pm
It’s too bad this list was compiled before last night’s Joaquin Phoenix “interview.”
Dave: “We owe Farrah Fawcett an apology.”
Dave: “So, what can you tell me about your days with the Unabomber?”
Dave: “Joaquin, I’m sorry you couldn’t be here tonight.”
Ha ha… Letterman is the absolute best there is in these kinds of awkward situations.
February 12th, 2009 at 4:33 pm
Check out his Oliver Reed interview!
February 12th, 2009 at 3:35 pm
I came across this a couple of weeks ago. I just thought that you may want to consider addding Joaquin Phoenix’s appearance from last night (02/11/09) to the list - making it a “top ten” list.
February 12th, 2009 at 12:31 pm
funny vid, i will uploaded this to tall dating site—Tallmingle.com— to share with my best friends,especially the hot models.
February 12th, 2009 at 11:32 am
After last night’s show, you gotta give Joaquin an honorable mention!!
February 12th, 2009 at 8:00 am
Yep Jaoquin’s is the new number one.. That was the very definition of awkward.
February 12th, 2009 at 12:19 am
i just watched letterman tonight with Joaquin Phoenix, and i must say that was incredibly awkward. Jaoquin didn’t really say anything and Dave was being a total dick.
February 10th, 2009 at 9:04 am
[...] while we’re at it, Letterman’s 9 Most Awkward Moments from [...]
February 9th, 2009 at 9:53 pm
[...] Letterman’s 9 Most Hilariously Awkward Moments [...]
February 9th, 2009 at 5:45 pm
[...] 9 Most Hilariously Awkward Moments Letterman’s 9 Most Hilariously Awkward Moments | Cracked.com __________________ SOT - …. I dunno, i wasnt really paying [...]
February 9th, 2009 at 12:50 pm
Madonna is asolutely annoying. A hundred years of Kabballah won’t save her from the hellfire specially placed to punish her for this moronic interview alone.
February 9th, 2009 at 10:18 am
woo! go craig ferguson!
February 8th, 2009 at 10:06 pm
Cher?
February 8th, 2009 at 4:09 pm
An Elliott Smith reference garners a +1 Internets to you, sir.
February 8th, 2009 at 1:42 am
Man, I forget how funny Dave can be. I haven’t really watched him in years, but I remember watching some of these. Carson was great coming back from a bomb and Dave is great at riding the trainwecks. As much as I’ve loved Conan, I think he’ll lose what’s left of his edge for the earlier slot. I know Craig Ferguson is supposed to be great, but I’m not ready to be hurt again.
February 6th, 2009 at 4:43 pm
Where’s Billy Idol? Nastassja Kinski? How soon we forget…
http://www.youtube.com/watch?v=7jxsfsIwc38
February 5th, 2009 at 12:12 am
Kid trips out after trip to dentist: the REMIX! hilarious!!! I’ll have what he’s having…
http://www.tokillfor.com/view_video.php?viewkey=5690823d30d15269a980&page=1&viewtype=&category=rf
February 4th, 2009 at 9:58 pm
Two quotes from the commentary on the Crispin Glover appearance:
“Twenty years later, debate still rages….Fake or real….”
“My question is how they did a rehearsal interview without realizing the guy was on [drugs]….”
Seems to me that the question, if valid (talk show interviews are supposed to be spontaneous conversation, inconsistent with being rehearsed, but please note that I do say “IF”), is a compelling argument for “fake’!
February 4th, 2009 at 1:47 pm
[...] Letterman’s 9 Most Hilariously Awkward Moments [...]
February 4th, 2009 at 9:18 am
How is the Andy Kaufman - Jerry Lawler interview not on this list. It should be #1.
http://www.youtube.com/watch?v=11T_-k7ckrg
February 3rd, 2009 at 4:40 pm
[...] found this online yesterday. It’s all about interviews where Dave shines. When he has no respect for [...]
February 3rd, 2009 at 12:51 pm
The Oliver Reed interview needs to be on this list
http://ca.youtube.com/watch?v=f9aSFkSCyw8
February 3rd, 2009 at 3:17 am
His interview with Emma Thompson is amazing as well. He obviously has never seen a Harry Potter movie, nor gives a flying fuck about them. And when she tells him she’s still in high school, he has to take a just a second to let that sink in. Looks like I’m not the only one.
February 3rd, 2009 at 12:17 am
[...] would want to watch that. It’s simple. If Letterman goes after him like he has done with Paris Hilton, Harvey Pekar, Bill O’ Reilly or any other number of guests, it will be absolutely [...]
February 2nd, 2009 at 1:40 pm
If you can find it, try Letterman’s interview with a coked-out-of-her-mind Natasha Kinski. Beyond belief
February 1st, 2009 at 5:58 pm
You totally forgot the interview with Gillian Anderson when they kiss.
url:youtube.com/watch?v=b2Z8UvXjgG8
February 1st, 2009 at 4:57 pm
[...] Letterman
February 1st, 2009 at 12:58 pm
Man… I haven’t really watched late night talk shows like this in a while (unless Daily and Colbert count). I lost interest at an early age when Johnny left..
But damn, I should have kept watching Dave. I had no idea he was that f***ing hard core with his! He just doesn’t give a s#!t! Now he’s going to retire, and leave whichever Jay Leno’s taking his place. sigh.
January 31st, 2009 at 5:19 pm
One I will always remember is when he asked Bette Davis, on the show to discuss her autobiography, when she lost her virginity.
She just glared at him and said nothing for several seconds. If looks could kill. Only time I’ve seen Dave put in his place so soundly. I think he even blushed.
January 30th, 2009 at 7:00 pm
Stupendous article, Swaim. Hilarity.
January 30th, 2009 at 2:26 pm
[...] ** Check out the 9 Most Hilariously Awkward David Letterman Moments. [...]
January 30th, 2009 at 12:08 am
[...] Letterman’s 9 Most Hilariously Awkward Moments [...]
January 29th, 2009 at 10:49 pm
Sam Phillips, who owned Sun Records in the 50’s and famously sold Elvis Presley’s contract to RCA for a relatively small sum, was on the old Letterman NBC show. He was drunk and kept asking Dave when he was going to get his teeth fixed. He only lasted for one segment; after the commercial, he was gone. They showed him on camera later, passed out in the Green Room. It was great.
January 29th, 2009 at 9:19 pm
[...] Letterman’s 9 Most Hilariously Awkward Moments [...]
January 29th, 2009 at 9:06 pm
[...] Most awkward Letterman interviews. [...]
January 29th, 2009 at 5:19 pm
Oh, and I’d say don’t feed the trolls, but it seems they’ve resorted to cannibalism.
January 29th, 2009 at 5:13 pm
There’s another paris hilton interview that’s hilarious, too. Actually, I think there’s two more. Come to think, it’s just pretty funny whenever she opens her mouth, but Letterman shows no mercy. It’s like feeding a slightly droopy-eyed skanky baby to a lion.
January 29th, 2009 at 7:54 am
[...] Letterman’s 9 most hilariously awkward moments. [...]
January 29th, 2009 at 5:04 am
[...] Letterman´s 9 Most Awkward Moments (Cracked) [...]
January 28th, 2009 at 4:31 pm
Craig Ferguson’s shelf life expired and he became another creepy-aging-guy cliche when he got married and to a younger woman. And then kept driving the subject into the ground on air. So boring. Next.
January 28th, 2009 at 4:11 pm
Top 9???
The interview with a completely spaced out Farrah Fawcett is one of the greats.
January 28th, 2009 at 3:40 pm
why does every single website with a comment section have stupid ass fights?
Im starting to think youre all one asstard.
go outside. STFU
January 28th, 2009 at 10:17 am
“And yes, maybe we don’t have anyone to enforce the rules but it’s sort of implied isn’t it?”
In where, the Cracked.com bylaws? Gee, I must have lost my copy. I’ll go look for them right now. Maybe you can find me the place where it says no one’s allowed to say anything not strictly pertaining to the article.
“There’s also quite innapropriate things, such as politics on a humour website, couldn’t you be a little more respectful to people who don’t want to hear your views?”
No. No one asked whether I wanted to hear their political views before airing them. I merely replied to another comment. I’m pretty tired of arrogant Liberals thinking they’re the only ones allowed to make political comments wherever they like.
January 28th, 2009 at 10:09 am
“And I always think it’s hilarious to poke at people with absolutely no knowledge of what they’re talking about ”
Me too… which was why I replied to you in the first place.
January 28th, 2009 at 8:40 am
“I always think it’s hilarious when someone goes out of their way to make a post just to let me know they have nothing to add to the discussion. “Wow… everything you said is SOOOO wrong but I can’t be specific.” Okay, thanks a bunch.”
And I always think it’s hilarious to poke at people with absolutely no knowledge of what they’re talking about without making the effort of trying to explain them where they’re wrong, since that won’t do anything anyway.
Guess we both win!
January 28th, 2009 at 3:17 am
[...] David Letterman’s 9 most hilariously awkward interviews. [...]
January 28th, 2009 at 2:33 am
I got one sentence in and I logged in to inform Swaim, whether he was serious or not about this, that Craig Ferguson sucks. The only thing funny about his show is that…it’s still on. But even that’s only smirk-funny.
January 27th, 2009 at 11:37 pm
Harvey Pekar totally kicked Letterman’s ass. Letterman kept tyring to make him out to be a buffoon but Letterman himself ended up looking like a buffoon.
January 27th, 2009 at 11:29 pm
Whoah Crispin… You seemed so NORMAL……
January 27th, 2009 at 9:30 pm
How isn’t one of the highlights for Harmony Korine when Dave says “This, by the way, is why they invented child-proof-caps”? That was one of the best lines in that one.
January 27th, 2009 at 7:21 pm
I think one of the most awkward moments I ever witnessed was when Drew Barrymore flashed her boobs for him on his birthday. Mainly because he had just been saying how fatherly he felt towards her and had since the beginning. But it probably doesn’t fit this list because he wasn’t being a prick. But the look on his face that he held for a good long time was priceless.
January 27th, 2009 at 7:04 pm
I’m not saying anything more to you, you’re a troll who just wastes everyone’s time.
You’re just another whiny, arrogant, hateful human being who alines themselves as a ‘Conservative’ without proper respect for that term’s meaning or history.
January 27th, 2009 at 5:46 pm
You come here all the time, go completely off topic and start a pathetic political discussion that only ever pushes your own agenda.
And yes, maybe we don’t have anyone to enforce the rules but it’s sort of implied isn’t it? There’s also quite innapropriate things, such as politics on a humour website, couldn’t you be a little more respectful to people who don’t want to hear your views?
January 27th, 2009 at 5:41 pm
The DL bit where Andy Kaufman and Jerry Lawlor was just that: a bit. Letterman walks a fine line between ratings genius and ratings whore; for someone who has lasted in media as long as he has, i would be surprised if he has not been at least aware of whatever sensationalist spin of any segment in this article. He did still plug the book/newsletter/magazine of Harvey Pekar. If you are on the DL show you’re going to get noticed, and there is no such thing as “bad publicity”; Dave was just ahead of his time, or maybe even a trend-setter.
This article itself will introduce people to the guests that would never have heard of them otherwise.
January 27th, 2009 at 5:39 pm
“CavalierX, don’t say somebody else has nothing to add to a discussion that has no real place here in the first place.”
I wasn’t poking at Code for having nothing to say, but for going out of his way to make a comment just to SAY he had nothing to say. Honestly, if you’re going to bother to type, say something funny or interesting or at least pertinent to whatever discussion is taking place. And I’m not sure when we elected someone to make sure all discussions stay on topic, but I don’t remember who I voted for.
January 27th, 2009 at 5:32 pm
CavalierX, don’t say somebody else has nothing to add to a discussion that has no real place here in the first place.
Do you go to a political blog and spam the comments section with dick jokes?
January 27th, 2009 at 5:27 pm
“CavalierX is spouting more shit than FOX News entire toilet can handle.
There’s just so much wrong with that last post that I don’t even know where to begin laughing at him.”
I always think it’s hilarious when someone goes out of their way to make a post just to let me know they have nothing to add to the discussion. “Wow… everything you said is SOOOO wrong but I can’t be specific.” Okay, thanks a bunch.
January 27th, 2009 at 4:57 pm
What about the one when that guy spencer from the hills was on there.
I dont know much about the show the hills or spencer, and I think Dave nailed it on the head
He asked, “why are you famous or why are you on my show” . . . . etc
Hilarious
January 27th, 2009 at 3:42 pm
Come on! Who takes Crispin Glover seriously? Watch Rubin and Ed, you’ll fuckin see what I mean.
January 27th, 2009 at 3:25 pm
CavalierX is spouting more shit than FOX News entire toilet can handle.
There’s just so much wrong with that last post that I don’t even know where to begin laughing at him.
January 27th, 2009 at 2:51 pm
bill o reilly is a prick Fuck that dude.
January 27th, 2009 at 2:51 pm
“…Then she and Alanis Morisette will hang out in a ranch house and compose ill-informed songs about linguistic concepts.”
*insert sound of milk-spewing nose-snort here*
Epic win.
January 27th, 2009 at 1:16 pm
Most of these were pretty funny, but the segment with Harmony Korine had me in stitches.
January 27th, 2009 at 1:12 pm
[...] bill that will save us all. - How airline crews train for crashes. - Nine awkward Letterman moments. - This list of funny Super Bowl commercials is nothing without the housecat herders, but still [...]
January 27th, 2009 at 1:08 pm
Hi, Michael.
January 27th, 2009 at 12:37 pm
Hey CavalierX and Kodiak. Why don’t you two exchange phone numbers and give each other a call. You guys are giving me a headache. Enough with the trolling already. Please.
January 27th, 2009 at 12:33 pm
I like David Letterman.
January 27th, 2009 at 12:22 pm
The Crispin Glover interview is legendary. Crispin himself to this day won’t give a straight answer about his appearance that time (he has since been on Letterman, and a bit more relaxed). Regardless, he was appear “in character”–specifically the character of “Rubin” from his movie, “Rubin and Ed.” He wasn’t on drugs, contrary to popular belief.
January 27th, 2009 at 12:08 pm
Now how the hell did you all end up arguing about Iraq?
goddammit
anyway, great article as always Swaim!
January 27th, 2009 at 10:40 am
[...] 9 Most Hilariously Awkward Letterman Moments January 27, 2009 - 10:37 am By COED Staff • 9 Most Hilariously Awkward Letterman Moments [...]
January 27th, 2009 at 9:56 am
“I honestly can’t puzzle that one out.”
Yes, you can. It was perfectly clear. Try harder.
“Iraq was not allied to Afghanistan, and did not declare war on the US.”
We were not really at war with Afghanistan, but with the Taliban thugs controlling that country and the terrorists with whom they were allied… and of whom Saddam was a huge supporter. On the other hand, you seem to have forgotten that we were ALREADY at war with Iraq. That war was in a cease-fire condition since 1991, when Saddam agreed to turn over all his secret projects for destruction within 90 days. He never did. Hell, we never even knew about his bioweapons program until his own son-in-law defected in 1996 and turned over evidence that, yes, Saddam was still going at it. Even Saddam’s top people were absolutely convinced that there was a secret storehouse of illegal weapons, which was never found. However, we did find several secret labs — all recently cleansed of evidence — and lots of mustard and sarin shells, all buried and degraded. If there was something there, the CIA let it slip through their greasy fingers.
January 27th, 2009 at 8:46 am
Arguing on the internet…
…Running in the special olympics…
..still retarded…
…sigh.
January 27th, 2009 at 8:40 am
When I get back from work this evening, I’ll be happy to carry on with this off-topic trolling.
January 27th, 2009 at 8:39 am
I was happy to read that link. I was especially interested in the very first page of the PDF, in which all the cassi bellum were related to Iraq’s famous stockpiles of weapons of mass destruction. I think we all remember about the WMD’s. The mysterious, invisible, intangible WMD’s. Oh, they’re out thee somewhere. A friend of a friend saw a blurry video tape of an Iraqi WMD lumbering away through the thick forests of the Pacific Northwest.
January 27th, 2009 at 8:32 am
I know about the Lend-Lease, I know about our aid to the UK, USSR and french resisitance.
What I don’t know is what exactly you were trying to say earlier with your little analogy in which Pearl Harbor was 9/11, Japan was Afghanistan, and Germany was Iraq. I honestly can’t puzzle that one out. The many people who now oppose the invasion of Iraq are the same as those few who, decades ago, opposed the war against the Third Reich? Germany was allied to Japan, and declared war on the US independently. Iraq was not allied to Afghanistan, and did not declare war on the US.
January 27th, 2009 at 8:28 am
In the Simmons clip, the dangling tray is in fact an rigged explosive
device to screw with Mr Simmons.
That’s why he doesn’t know what it is and Letterman insists it be put in the proper position:
He’s being set up.
Believe me I know, though anyone can see what’s up if they think for a second.
That said, I know for a fact.
January 27th, 2009 at 8:24 am
“If I were president I’d hang the man who tried to kill my daddy, too.”
You seem not to realise that attempting to assassinate a former US President is considered an act of war by some, no matter who that President is. You also must have forgotten that that and all the other reasons for removing Saddam for power were clearly spelled out in the Authorisation for Use of Military Force Against Iraq. Guess you should try reading THAT sometime, too.
http://www.c-span.org/resources/pdf/hjres114.pdf
January 27th, 2009 at 8:21 am
“Nice try, Cavalier, but Hitler declared war on us. Read a book sometime, you know, instead of burning them.”
Was that supposed to be clever? Clearly you know nothing of history. Maybe You shoudl try reading a book sometime. Hitler only declared war on us because we were aiding England. We gave them 50 destroyers, escorted their convoys so the Germans couldn’t attack and enacted Lend-Lease so we could give them war materials for free.
January 27th, 2009 at 8:15 am
Nice try, Cavalier, but Hitler declared war on us. Read a book sometime, you know, instead of burning them.
As a side note: I’m not stupid enough to the think Iraq was invaded for the oil. Nor am I stupid enough beleive it was an act of heart-warming altruism. It’s been made quite clear that Bush started the Iraq War for his own personal reasons. If I were president I’d hang the man who tried to kill my daddy, too. Then again, maybe that’s why I should never become president.
January 27th, 2009 at 8:15 am
Oh, and 15 of the 19 9/11 hijackers were Saudis, not Afghani. Al-Qaeda wanted to use as many Saudis as possible for that attack in the hope that we’d just blindly declare war on Saudi Arabia. Two were from UAE, one was Egyptian and one was Lebanese.
January 27th, 2009 at 8:00 am
“David’s response was the correct one, in that he stated it wasn’t Iraqis who were responsible for the WTC bombings (the bombers were Afghani, whether or not Iraq had a hand in it is still not positive), so there was really no reason to go and mess with them.”
Believe it or not, there were people who said the same thing about the Germans in WWII. Hey, they weren’t responsible for Pearl Harbor (John Belushi jokes aside), why are we going after them? But the Germans were allied with the Japanese and poised to crush Europe while we were looking elsewhere, just as Saddam was supporting international terrorism and was poised to stir up a lot of trouble in the Middle East while we were occupied elsewhere. Bush’s biggest mistake there was letting the press play up the WMD angle (cause that was SCARY! and sells papers) and not making more out of Saddam’s history of terrorism support. His second biggest mistake was not exposing the massive UN corruption — France, Russia, Germany and China were all taking oil money from Saddam the whole time, as were his biggest supporters in the UK and USA.
January 27th, 2009 at 7:50 am
“I feel that way about “Do you want Obama to succeed?” for the most part. You can’t answer it without defining succeed, but you’re just supposed to say “Yes.””
Actually, I always answer that with the question, “Succeed at what?” Because I’ve never heard anyone ask whether I wanted any other President to succeed. What’s so special about this one that makes whether he will “succeed” a question?
January 27th, 2009 at 7:35 am
Number 6 is my favourite, before she changes the subject Letterman looks like he’s about to yell at her to hand over her car keys, credit cards and then go up to her room.
January 27th, 2009 at 7:18 am
Crispin was owning Dave in his own esoteric fashion. Letterman himself acknowledged it in Esquire magazine. It’s just some comic weirdness that most people won’t understand.
January 27th, 2009 at 6:37 am
No mention of the wonderfully cringe-worthy Mr. T interview. He has to count to 10 to stop himself from punching Dave.
January 27th, 2009 at 4:31 am
What about Courtney Love’s appearance? The look on Letterman’s face when she flashes him, (like he’s about to choke on his own vomit), comes only second to her sloppy, drunken rambling.
January 27th, 2009 at 2:21 am
Thesaurus says that “truth” is the opposite of “rumor”. Or “tell truth”.
““Do you want the US to win in Iraq?” is a question with about as much meaning as “Do you want to eat lunch in the carburetor?” You just can’t approach it in any sensible way.”
I feel that way about “Do you want Obama to succeed?” for the most part. You can’t answer it without defining succeed, but you’re just supposed to say “Yes.”
January 27th, 2009 at 2:12 am
Shadowspawn, none of the hijackers were from Afghanistan. Many of them trained there, but they were almost all from Saudi Arabia.
January 27th, 2009 at 2:08 am
If there’s one thing we’ve learned from this list (at least #5 and #6) it’s to never, ever spurn Dave.
He was pissed at McCain for ditching his show at the last minute, and raked him over the coals with it. He was pissed at Hilton for going to jail when she was supposed to do his show, and so he made the whole interview about jail. Seriously, do not fuck with Dave.
“Do you want the US to win in Iraq?” is a question with about as much meaning as “Do you want to eat lunch in the carburetor?” You just can’t approach it in any sensible way. And that’s why Dave’s response was so priceless.
January 27th, 2009 at 1:50 am
O’Reilly’s question was most certainly a question to either push the Republican view on the audience or to browbeat and/or completely ream Letterman for being a “Communist left-wing freak” (or whatever the Republicans call people who don’t agree with their world views). David’s response was the correct one, in that he stated it wasn’t Iraqis who were responsible for the WTC bombings (the bombers were Afghani, whether or not Iraq had a hand in it is still not positive), so there was really no reason to go and mess with them. Mind you, the Democrats aren’t exactly clean themselves (hell, look at Blagojevich)…no politician has gone a whole campaign without spouting bullshit out of every orifice.
This is probably the biggest reason I enjoy the comedy of The Capitol Steps: they don’t take one side of any political issue, they lampoon it all (even the Green Party and other independents).
January 27th, 2009 at 1:21 am
regarding ‘untrue’ or ‘unsure’ rumor…it is definitely not an oxymoron. It is actually the opposite in that the words are redundant. So it could be called pleonastic or tautological, but not an oxymoron.
January 27th, 2009 at 1:18 am
I’ve never watched the Glover clip through - he was in character it would seem. A very strange character. I agree that it might not belong on this particular list, but whatever; it’s all good.
January 27th, 2009 at 1:09 am
Loves me some Crispin Glover.
January 27th, 2009 at 1:03 am
Madonna ! wow, so FU****G hot …
Whatever yeah she’s kinda childish, but damn, she looks like alot of fun !
I though they had a somehow good war between them. Dave threw some good ones, but madonna was always there to reply, and in an unexpected way.
I guess she has just been there to bother people, she just wanted to get attention. She’s not the nice little girl… that’s what she does.
January 27th, 2009 at 12:50 am
Thought Madonna would be at the number one position for sure (and I say that as a fan). I had forgotten about Crispin Glover. Good calls on all of them.
January 27th, 2009 at 12:41 am
I forgot how much I hated Madonna. Thanks for the reminder.
January 27th, 2009 at 12:17 am
George McFly is way more badass than I ever thought.
“Dave, you are my density… HI-YA!”
Thank you for this, Swaim!
January 27th, 2009 at 12:16 am
As has been pointed out already, Crispin Glover was obviously in character, appearing as Rubin from the now cult classic RUBIN AND ED. Man, I love that movie. If there’s a more awkward road trip film out there, I challenge Michael Swaim to find it and several others like it and then arrange them in a convenient list for my enjoyment.
That Glover clip really shouldn’t be on this list though, no more than Borat’s or Pee Wee Herman’s appearance should be.
January 27th, 2009 at 12:12 am
Dammit, I wanted the petulant reprisal - now when I get here you leave.
Shit.
January 27th, 2009 at 12:11 am
That Michael Richards bit was actively painful. Yowch! Was he on something or was he DTing or what?
I saw the Simmons one at the time; he’s a great guest because you can mock him to his face and he doesn’t mind so long as you let him get in his spiel.
Wait a minute, disliking Bill O’Reilly doesn’t make you a leftist. Trust me. There are plenty of reasons to dislike him. I think the political stuff here is usually very funny - like the liveblog of the presidential debates. Swaim doesn’t seem obnoxiously opinionated to me, and he’s really funny.
In this case I rather thought O’Reilly had a point and Dave is missing some stuff, but he did get in a good zinger; give him that much.
January 27th, 2009 at 12:01 am
Paris deserved that grilling, she’s not fucking “strong” for going to jail for a month for deliberately driving drunk! All she had to say was admit she fucked up big time and it would’ve been fine but she had to prove what a stubborn moron she is…or maybe she didn’t even realise she was proving what everyone suspects of her.
There’s no way I felt sorry for her during this.
January 27th, 2009 at 12:01 am
Yeah, it’s hailing where I am and I’m stuck inside. Although now I’m going to play Fallout 3, so feel free to resume normal commenting activities without fear of petulant reprisal.
January 26th, 2009 at 11:34 pm
Also, Swaim is commenting a whole lot this article.
January 26th, 2009 at 11:32 pm
The word Whelp is looking for is “redundant”. Swaim is right, it’s not an oxymoron, but it’s definitely redundant.
January 26th, 2009 at 11:29 pm
[...] I now tivo the David Lettermen Show because of your article. [...]
January 26th, 2009 at 11:26 pm
How can you leave out his interviews with Shirley McClain and Cher??
January 26th, 2009 at 11:15 pm
And also, I saw the Glover clip a long time ago and really did think that he’d gotten his hands on some bad acid. I was unaware of this “Rubin” character. I’m kind of disappointed now.
January 26th, 2009 at 11:10 pm
B. O’R.: “Do you want us to win in Iraq?”
DL: “Well, whatever ‘win’ means, yes, of course I do, but-
B. O’R. : “Well then you obviously agree with me that Bush is a brilliant tactician and we should blindly follow wherever he leads and send more and more troops overseas to “win” this glorious, Christian war against terror”
The point I’m trying to make here is that O’Reilly’s question was a setup. He asked a question that he assumed Letterman could only respond to by saying “why yes, sir”, thus setting up the rest of the interview so that O’Reilly could use it to push his ideas onto an audience that doesn’t watch his show. Letterman foiled this plan by actually putting thought into his response to an obviously loaded question.
January 26th, 2009 at 11:10 pm
“Sure rumor” would indeed be an oxymoron (or carbojackass, if you’re counting in metrics); as Swaim gracefully stated, the presence of “antethical words put together” is about sufficient to sustain that claim.
The coinage “untrue rumor” is, alongside the aforementionned “unsure rumor”, actually, more of a truism, or tautology; though I wouldn’t be so sure about the first, given that ALL rumors aren’t false (I’m referring to Madonna’s hidden adoption agenda here).
January 26th, 2009 at 11:09 pm
The reason I tend to take the side of Dave over the guest is that that guest is on to take up part of the show and entertain the audience. In exchange, they get to promote themselves and their latest project. You can’t come with nothing to the table.
And yes, Madonna’s “cool” attitude is just so childish. “I’m swearing, see? Fuck! Take that, establishment! And why do I have to leave, why do we have to follow the rules?” You have to follow the rules because there are two other guests waiting to come out, woman, and you’re gonna take up their time!
January 26th, 2009 at 11:08 pm
How do you know it’s angel dust he’s high on? And also, what is angel dust?
January 26th, 2009 at 11:06 pm
It’s kinda weird, but Dave and Madonna actually seem to have some chemistry here. Highly amusing. I forgot how awesome both Madonna and Dave can be.
January 26th, 2009 at 11:04 pm
Ferguson’s OK, but he is entirely too amused by himself.
January 26th, 2009 at 11:03 pm
Not that Bill O’Reilly would lift a finger to save any flaming person. HEYO!
He hates gays.
January 26th, 2009 at 10:46 pm
@Swaim: I guess if the orphans are already flaming, then there’s no use in saving them. Either way, you pretty much proved my point.
January 26th, 2009 at 10:44 pm
Actually, that still wouldn’t be an oxymoron I don’t think. “Sure rumor” maybe, but that’s about it, since an oxymoron has to be antithetical words put together. Rumors are unsure, so “unsure rumor” doesn’t work. I think the best oxymoron with rumor would be “verified rumor.” Am I totally wrong? Language people?
January 26th, 2009 at 10:33 pm
Martok: “As a fellow Irishman, I know how easy it is for us to get hot under the collar.”
Hahahaha whatever. How lame. Bill O’Reilly isn’t irish, he is an american. My grandparents came from germany, I don’t go around calling myself german.
Using ancestry as an excuse to act certain ways is complete bullshit. Saying its ok to get hot under the collar because you’re “irish” is analogous to saying it’s ok for me to cannibalize and eat human feces because I am “german”
January 26th, 2009 at 10:31 pm
She actually said “unsure” rumour, not “untrue” rumour.
This could be considered an oxymoron, since a rumor is not “sure” (certain) in the first place…
January 26th, 2009 at 10:30 pm
Crispins tray had an antique collection of wax replicas of diseased eyes which used to be used by doctors before the interT00bs..
January 26th, 2009 at 10:22 pm
All of which I will publicly recant if Bill O’Reilly saves a bunch of flaming orphans. You have my word. Although to be honest, I’d still probably say something like “Well, he may be a doddering lunatic, but fuck me if he didn’t save those orphans. Good on ya, BIll.”
January 26th, 2009 at 10:21 pm
Robert Denby: That’s the silliest thing I’ve heard today. Try being more elusive sometime.
And since when is it a comedian’s job to be politically impartial? It’s strange to me that people continuously act like they’ve caught me hiding some terrible secret when I blatantly reveal my values all the damn time. Not that I would call myself “unbelievably biased;” noticing that Bill O’Reilly is a doddering lunatic doesn’t really take that much liberalism. More just sense organs attached to a functioning brain stem.
January 26th, 2009 at 10:06 pm
The Craig Ferguson line was a joke, you guys. Are you all so young that you never heard of Carson?!?
January 26th, 2009 at 10:04 pm
“Then she and Alanis Morisette will hang out in a ranch house and compose ill-informed songs about linguistic concepts.”
Unless there’s been some newer AM song that has your panties in a bundle, you must still be kvetching about “Ironic,” 14 years after the fact. I mean, at the time, pointing out that “Ironic” wasn’t very ironic was kind of cute for about fifteen seconds…the sort of disposable humor made famous by morning DJ’s. One of the definitions of “irony” is “when the intended meaning or outcome is different than the actual one.” For example, consider the following sentence: “Swaim tried to be funny with his cutting-edge humor, but ironically, he failed.”
January 26th, 2009 at 10:03 pm
I thought for sure Drew Barrymore would be on here for the flash thing.
January 26th, 2009 at 9:54 pm
Toroid and Martok: To Swaim’s credit, he never pretended to be impartial. With that out of the way, he’s still an unbelievably biased left-winger who’ll attack anyone he disagrees with no matter how desperate and childish it makes him look. O’Reilly could run into a burning orphanage and rescue every kid there, and guys like Swaim would just bitch about how he didn’t wipe his feet before entering.
January 26th, 2009 at 9:39 pm
[...] Top 9 Awkward Letterman Moments Monday, 26 January 2009 — Shawn You can find all nine ••by clicking here••. [...]
January 26th, 2009 at 9:31 pm
this is why swaim is my favorite writer on here.
January 26th, 2009 at 9:20 pm
I don’t think Dave actually hates most of these guests, Harvey Pekar being an obvious and understandable exception. I think he’s just bantering, trying out some different approaches, including insults that don’t go too far, and letting his guests do the same. I think he could tell that he was making good television, even when his guests are swearing like sailors — the main exception being the interview with Paris, which is a trainwreck. Dave seems to think that if he keeps talking about jail and asking stupid questions something funny will happen, but he’s mostly wrong. Paris actually comes across as having her act together more than David, who seems to be drowning. But wow, that was Madonna’s best look, wasn’t it?
January 26th, 2009 at 9:19 pm
i couldn’t watch some of these they were so awkward…the michael richards one was just brutal
January 26th, 2009 at 9:05 pm
Key point, Raging Toroid. That was a more thoughtful response than anything Dave said, and, for once, O”Reilly was actually calm, cool, and collected during that interview. Bill O’Reilly is Irish and a man of passion. As a fellow Irishman, I know how easy it is for us to get hot under the collar. Mr O’Reilly gets excited sometimes and carries a reputation for being a bully, especially from members of the overly liberal media who truly fear him because he is the most watched news program on cable television and attempts to present a more centrist view. And yes, I mean it when I say centrist. The man has just as many crazy conservatives accusing him of being too liberal as he has looney liberals accusing him of being too conservative. When not shouting he is logical and coherent. He obviously loves this country and wants it to succeed. Sure, he may be cashing in a little too much by being overly sensational at times, but doesn’t Letterman do that too?
On a side note, I also find it funny that when I confront people whom I meet that openly criticize Bill O’Reilly’s program they freely admit to me that they have never seen it.
January 26th, 2009 at 8:53 pm
I’m sure someone’s said it already, however…
Prepare for Neurosis:
It’s Elliott. 2 & 2.
I’m sorry, it had to be said. I’m done now.
January 26th, 2009 at 8:16 pm
I’m not sorry to say this, but I didn’t feel an inch of sympathy for paris hilton. Also, didn’t Marilyn Manson have a really awkward interview or two with mr. letterman.
January 26th, 2009 at 8:06 pm
So, I watch the O’Reilly clip to see how this guy is supposedly such a jerk… yeah really no evidence of that here.
He asked a simple question. And no it isn’t a “have you stopped beating your wife question.” If you asked me that question I would have no trouble answering it. Neither would Bill O’Reilly.
Dave’s problem is simply that he can’t give an honest answer that doesn’t make him look really bad. And his comeback is not clever. You could give that response to any question.
“Did you cheat on me?”
“Well … you see … blah, blah blah”
“Did you cheat on me? It’s a simple question.”
“Well, not for me, because I’m THOUGHTFUL.” (cue applause)
Dave could have said, “Yes, I want the US to win in Iraq, but I think it should be done differently” Or he even could have said, “Yes, I want the US to win but I don’t think it’s possible.”
The harsh reality is these people didn’t want the US to win, even if the alternative was genocide. Proof? Now that the US has won and the result has been a massive decrease in violence (both from war levels and from Saddam levels) do you see any celebration from these people.
I remember from American Splendor when Pekar’s wife/girlfriend looks in dismay at the Letterman show and says something like “people watch this?” I know how she feels.
January 26th, 2009 at 7:58 pm
Yet another fantastic article. Swaim, you do no wrong. Letterman and Ferguson rule late night television.
January 26th, 2009 at 7:48 pm
MAD TV: Gay gangsta FIGHT!
http://www.tokillfor.com/view_video.php?viewkey=f278cff8c64602c15f49&page=6&viewtype=&category=mr
January 26th, 2009 at 7:15 pm
I don’t think that the Michael Richards one was really funny because he really tried to apologize. I thought that was really unfair to him.
January 26th, 2009 at 7:15 pm
Hah! I actually understood the Alanis Morissette reference…
January 26th, 2009 at 7:04 pm
WTF??
where’s the clip of Jerry “The King” Lawley breaking Andy Kaufman’s pencil neck with a piledriver?
January 26th, 2009 at 7:00 pm
[...] David Letterman is awkward. [Cracked.com] [...]
January 26th, 2009 at 6:43 pm
I thought I was the only person in the world who appreciates Craig Ferguson.
January 26th, 2009 at 6:37 pm
Oh, and Glover? Definitely acting. Unlike the true wasted rhythms that Korine gives off, Glover’s come off like attempts at garnering laughs through aborted non-punchlines.
Fun, though.
January 26th, 2009 at 6:19 pm
“Put that on my list to do: “SMOKE SOME ENDO! PEE IN THE SHOWER! GET THOSE PANTIES CLEANED!”
I actually had always sort of felt Dave had kissed up the way Madonna accuses him of doing, but these are gold and give me a newfound appreciation for Dave.
January 26th, 2009 at 6:16 pm
Madonna thought she was being so cool and provocative - look at me, I’m cursing and making dirty jokes and calling Letterman some names! She looked foolish, and Dave stood his ground.
January 26th, 2009 at 5:36 pm
Crispin Glover is not high. He really is acting. If you study Andy Warhol or ever heard any of this interviews you would see a lot of similarities.
January 26th, 2009 at 5:17 pm
Lettermen is a great interviewer. Doesn’t let guests off the hook easily.
But Conan remains the best late-night host!
January 26th, 2009 at 5:09 pm
“I love you Paris!” “I love you too!” “Someone you met in jail?”
Letterman is a fucking genius. I’m so glad he went after Hilton in this. Very fun to watch.
January 26th, 2009 at 5:08 pm
No mention of Andy Kaufman? Aww… those were classics.
January 26th, 2009 at 5:06 pm
I’ve never seen this show before due to being in England. It seems like a laugh, but is this standard business for this guy, or are these just exceptional moments?
Also, Swaim, great article and all, but can you guys try to keep video articles short please? We don’t all have the time to watch a thousand hour-long videos just to understand a few jokes.
January 26th, 2009 at 4:56 pm
“I’ll buy you a parakeet!”
Where the hell did that come from? Is there some story behind Paris Hilton and parakeets?”
January 26th, 2009 at 4:28 pm
David Letterman has such a way with making people squirm in their seats, it almost makes the viewer uncomfortable. This was fantastic.
January 26th, 2009 at 4:24 pm
[...] Enjoy…or should that be cringe? Spread the Word: [...]
January 26th, 2009 at 4:23 pm
With the fucky wig I say Crispin Glover was doing his weird thing. Let’s face it, the guy’s the epitome of kooky.
January 26th, 2009 at 4:22 pm
When I saw the title, I immediately remembered one of the times Dave had an animal guy come on the show, and he brought out a baboon which had an enormous boner, and which got taken off the stage almost immediately. I’m assuming that this clip was left out solely because it doesn’t seem to be on YouTube.
January 26th, 2009 at 4:12 pm
Bill O’Reilly should really stop going on other people’s shows, everywhere he goes he gets his ass handed to him, or at the very least when he goes on shows like Letterman, The Daily Show or the Colbert Report, you know, the guys HE says are not prepared to be on TV. It really cracked me up when that video of him not being able to read the teleprompter came out, some time after he had being saying that Jon Stewart and Stephen Colbert didn’t know what to do on their shows because their teleprompters were empty as a result of the writers strike.
January 26th, 2009 at 4:06 pm
check out letterman’s interview with marilyn manson. it trumpsany other letternman interview for awkwardness
January 26th, 2009 at 3:54 pm
I’d just like to point out that Madonna is clearly high out of her fucking gourd. Honestly- look at how she giggles inappropriately, sways in the chair and leans over everything, and makes completely random subject changes (DON’T MAKE ME PLAY THE FOOL DAVE…do you want to touch my dress), not to mention the stoner speak (the ranting against money “You just kiss up to everybody man, you changed”) High as a fucking kite.
January 26th, 2009 at 3:52 pm
Oh man, I didn’t realize how witty and funny Letterman was until I saw this. The man is a genius. He always knows when to say the right thing. I envy that.
The only people who don’t like him are inbred hicks.
January 26th, 2009 at 3:50 pm
A good recent example is Letterman’s interviewing of Lauren Conrad of “The Hills:” “Did you ever think that maybe YOU’RE the problem?” The look on Lauren’s face is pretty amazing.
January 26th, 2009 at 3:49 pm
captain beefheart on letterman is pretty weird, they’re cutting the beaks off of pelicans in california.
January 26th, 2009 at 3:41 pm
Regarding Harmony Korine: His success in the total proof that there is a zionist conspiracy promoting the work of even the most talentless jews (also the same people who say the ultra disgustingly skinny Natalie Portman is hot).
And no, I’m not racist. But c’mon, if Richard Dreyfus wasn’t jew his career would have died after First Encounters along with Steven Spielberg’s.
January 26th, 2009 at 3:37 pm
Craig Ferguson is awesome, and I now love you for saying what you did about him.
January 26th, 2009 at 3:35 pm
Commenter Greene lost me when he referred to America as “Amerika”
WUTS RONG WIT JU AMERIKKKANZ!? 3RD WURLD POWAH
January 26th, 2009 at 3:20 pm
Wow, I can’t believe andy kaufman’s appearance didn’t win…..
or at least mentioned AT ALL.
you dissapointed me big time this time Cracked.com…..
January 26th, 2009 at 2:46 pm
I just LOVE the look of utter defeat on O’Riely’s face when letterman OWNED him. Maybe bill wouldnt be such a piece of shit if hed just go ahead and come out of the closet then learn to actually read something that isnt preceded by the phrase “republican bullet points.” After all there is no one at all in that party with any grasp on reality or the constitution.
January 26th, 2009 at 2:46 pm
An Elliot Smith reference! Finally! I feel like I’ve waited all my life for that…if Swaim starts talking about Sleetmute Nightmute and Joe Cotten in his next article my life will be complete.
January 26th, 2009 at 2:08 pm
How do people find Letterman funny? He’s a sardonic corporate yuppie who attempts to make fun of people that make less money than he does, then fails fantastically, yet people still laugh. What’s the matter with you, people of Amerika?
And Harmony is awe-inspiringly twitchy. Do drugs make people awesome? Is that why the government doesn’t like them?
January 26th, 2009 at 2:00 pm
You gotta love Paul’s band, though. The machine blows up, Richard Simmons scampers off in terror, and they immediately start in with the ‘add insult to injury’ jazz riff.
January 26th, 2009 at 1:41 pm
every other awkward moment on Letterman: EVERYTHING ELSE. the bastard’s not funny.
January 26th, 2009 at 1:36 pm
As soon as I saw this list, I knew what was gonna be #1. You have to hand it to Crispin, the man’s a genius . . . people are still falling for that routine.
Last time, kids: This is a CHARACTER he plays in a MOVIE called “Rubin & Ed”. It is NOT Crispin on drugs. You know, it is possible for someone to be eccentric entirely under their own power.
The things in the case are Victorian-era models of diseased eyes.
January 26th, 2009 at 1:30 pm
I love the angry Repugnicans that pop up the second one of “their own” gets laughed at.
McCain still lost, Palin is still a stupid cunt and O’Reilly still deserves a punch in the uterus.
Get over it.
January 26th, 2009 at 1:27 pm
This is an awesome list, but you totally lost me by saying Craig Ferguson is the best Late Night host. Are you serious? Even Leno is better than that fruitcake.
January 26th, 2009 at 1:12 pm
Classic uncomfortable was the Andy Dick interview after the Suddenly Susan actor died. Dick gave this ‘I’m out of rehab and turned my life around’ speil and Dave just sighed and looked at his desk.
See Swaim, we’re already giving you material for part 2. We’re helping.
January 26th, 2009 at 1:07 pm
I can’t believe you didn’t include the amazing Jane Pauley episode. The one where Letterman let the audience vote on everything. Pauley almost bolted when the audience voted her into a dentist’s chair for the interview, but when they voted to have her voice modified electronically to sound like she’d inhaled helium, she simply refused to say another word. It was a classic.
And of course, there were the times that Sandra Bernhardt and Dr. Ruth got Letterman so flustered and embarrassed that he literally walked off the stage.
January 26th, 2009 at 1:06 pm
I have a newfound respect for Letterman. Still, none of these compare to the interviews with Hunter S. Thompson on Conan O’Brien.
January 26th, 2009 at 12:20 pm
Oh, Dave. Your wit astounds me.
The only people I find considerably more obtuse than David Letterman are his audience members. And Jay Leno. And Dennis Miller. You can see where I’m going with this.
I sincerely hope Christian Bale is invited to be a guest on this show sometime in the very near future. And takes care of things.
January 26th, 2009 at 12:11 pm
I remember once when Dave made Richard Simmons put on jeans and a flannel shirt. He looked so sad.
January 26th, 2009 at 11:52 am
I’m saying first.
January 26th, 2009 at 11:50 am
It only takes 5 tranquilizers for me to find Dave funny.
January 26th, 2009 at 11:46 am
Is everyone here too young to remember Andy Kaufman? Yeah it was staged but that was a very awkward moment on Dave–getting hit in the face by a professional wrestler.
January 26th, 2009 at 11:45 am
I remember seeing an awkward moment on Late Night with Conan O’Brien, but it wasn’t awkward because he was a “dismissive prick,” it was awkward because all of the laughter in the studio died suddenly and without reason, all at once. Rachel Dratch (from SNL) was the guest, and I don’t even remember what was said, but everyone was laughing hysterically and then all of a sudden, dead silence. Conan yelled, “What happened??” immediately after, and if I remember correctly, Rachel responded with a weird screech of laughter.
January 26th, 2009 at 11:10 am
Oh, and yes, I believe much of the Letterman / Simmons relationship is staged, though I think they may irritate each other a little in real life. I think it’s more like the old Letterman / Charles Grodin interviews where they act like they hate each other.
I want to add that you have to appreciate Jerry Seinfeld’s willingness to help out Richards as best he can, even though he, like everyone else, realizes this was a terrible idea.
And finally, while the Madonna of this stage started losing me back in the day, I would like to hear her comments unedited. And I shall also add that the Vogue / Express Yourself era Madonna aroused me to no end.
January 26th, 2009 at 11:08 am
FAKE! The interview with Harmony is staged by locust overlords. You can clearly hear them chattering to each other in triumph at the 7:22 mark.
Earthlings must band together to destroy this Letter-MAN and save Harmony!
January 26th, 2009 at 11:07 am
hmm. this totally should have been done in swaim video form.
January 26th, 2009 at 11:06 am
Personally, I believe this attitude is partly the reason why I like Letterman. He can only tolerate so much celebrity bullshit. It’s also his main difference from Leno, who excels at happy, ass-kissing interviews. To some, this makes Dave look like some jerk and Jay your happy TV friend. I prefer Dave, a guy who seems to genuinely dislike his own show.
Now, while I’ve kind of gotten annoyed how obvious Dave’s dislike of Bush is, and that he’s undoubtedly a politically liberal kind of guy, I like that with O’Reilly, you can almost see him just get fed up and realize he just cannot get himself to deal with O’Reilly calmly and without any bias. And if I may again bring up the comparison, can you ever imagine Jay Leno in a million years arguing with a guest like this? Whether that’s a good thing or a bad thing is up to you.
January 26th, 2009 at 11:04 am
In 9 it’s an obvious joke, Simmons’ reaction to the steamer exploding is priceless, but staged.
In 1 Crispin is playing a character, and if people are so deluded to be convinced that it’s his actual nature, it just proves how great an actor he truly is =D
The Paris one is brutal though, I remember seeing it when it was on tv and having to eventually change the channel.
January 26th, 2009 at 11:00 am
Maybe because “Do you want us to win the war” is such a meaningless phrase to begin with, in that it is not as much a question as it is a leading statement in the vein of “When did you stop beating your wife?”.
January 26th, 2009 at 11:00 am
That wasn’t Crispin, it was Rubin Farr, Crispin’s Tony Clifton.
January 26th, 2009 at 10:59 am
I read somewhere that Crispin Glover’s case was full of Victorian-era gynecological models. Not kidding.
January 26th, 2009 at 10:58 am
This was some pretty funny stuff, I feel like I should start watching Letterman more just in the hopes of catching an interview like this. The only one of the people in question up there I actually kinda started to feel bad for though were Michael Richards (what he did has no excuse, but he seems genuinely upset and apologetic) and Paris Hilton (as Swaim said, defying everything my brain thinks is right).
January 26th, 2009 at 10:54 am
To find Letterman funny, you have to remember that he’s not a really a comedian, just a crotchety old man.
January 26th, 2009 at 10:49 am
honestly it’s no good if an interviewer just sits there and laughs at his guest
January 26th, 2009 at 10:48 am
I love Dave but he’s a real jerk in that Crispin Glover vid. Just trying to make the kid feel even more uncomfortable.
January 26th, 2009 at 10:46 am
So do you get a check directly from the DNC for this bs or what?
January 26th, 2009 at 10:38 am
Bill O’Reilly embodies every single thing that’s wrong with America: Self-righteous, deaf to solid reasoning and logic, willing to use kindergarten tactics in arguments and generally being too right-wing.
January 26th, 2009 at 10:21 am
“Maybe O’reilly wouldn’t have had to repeat the question if Letterman had actually given an answer.”
I laughed but not because you’re right.
January 26th, 2009 at 10:12 am
wow i rather watch maddona talking to letterman than to actually hear her sing. crispin glover was just hillarious
January 26th, 2009 at 10:09 am
i can’t believe you left out the farrah fawcett interview.
January 26th, 2009 at 10:05 am
#7. Michael Richards. i’ve said this ever since i heard about this whole deal. this is how i would have handled it.
“You see. It shocks you. But, what does it mean? What does Nigger mean? EVERY Race has it’s own, but not everyone is one. Hispanics. Lazy, border hoppers hanging around home depot, selling oranges. NOW, like I said, not everyone is one.
White people. Ours ranges from both sides of the money wheel. Poor, redneck trailer trash who live off of welfare and foodstamps, not bothering to even TRY to better themselves. Then you have the rich business executives who piss on the homeless and ruin peoples lives without even giving a fuck.
Black people. This ones a little hard because you have nigg-UHS, and Nigg-ERS. Your nigga is the guy who gives you ‘the hook up’. He’s there for you when you need him, and vice versa. He’s your bud, your friend, your homie, your ‘nigga’.
THEN theres nigger. Thats the person who can’t hold a job and then blames everyone else. He has 9 kids by 8 different women. Lives in a broke down house, drives a broke down car, but has $4,000 rims and a $2,000 sound system in it. And they LOVE talking during the movies……OR AT COMEDY CLUBS.
January 26th, 2009 at 9:57 am
(sorry, nobody’s ever going to top Craig Ferguson)
you just earned like 1000 points right there, swaim.
you cheeky monkey.
January 26th, 2009 at 9:49 am
I felt really kinda bad for Crispin Glover. I really don’t think he was high. I’ve known guys like him. He’s just ridiculousy nervous, and weird as hell.
January 26th, 2009 at 9:33 am
I think Letterman and Richard Simmons are friends but just play these parts with each other. It seems like Richard Simmons is on the show every few months, despite the fact he doesn’t really do anything noteworthy, and he and Letterman always do this schtick together. But that’s just me.
January 26th, 2009 at 9:31 am
Wow, that Harvey Pekar interview was almost uncomfortable to watch.
I swear, I know a guy EXACTLY like that.
January 26th, 2009 at 9:24 am
Maybe O’reilly wouldn’t have had to repeat the question if Letterman had actually given an answer. Maybe you missed that part…cause you’re “thoughtful”…
January 26th, 2009 at 9:08 am
I’m not saying first.
January 26th, 2009 at 9:04 am
Glover was playing a character from his then-upcoming movie Rubin and Ed.
January 26th, 2009 at 9:04 am
Like Mr. Farr, get it?
January 26th, 2009 at 8:51 am
What, no Marilyn Manson?