Wait Wait Don't Tell Me's greatest moment ever

YES. I laughed until my sides hurt.

I can’t remember who it was, but I think one of the celebrity guests volunteered to record the answering machine message when he didn’t get two out of three correct.

Yesterday’s show featured a call-in contestant who is a Microsoft software engineer who works on Word. I can’t believe they missed the chance to grill her about Clippy!

Oh, the Romney line was great! I was laughing so hard I was afraid people were going to be staring at me! I really should not listen to the show while driving!

I love the Clippy segment, and the time Paula cross-examined some Supreme Court justice on his robe. And then there was the time Carl was doing some story about I have no memory of what, and he broke into a little mouse voice…I had to pull over and stop it was so funny! I always listen at work on Sunday’s and am so looking forward to today’s show, but my boss is working with me today so I might have to listen later. I was really disappointed i couldn’t go to the taping they did here in Cleveland a few weeks back.

that was SCOTUS justice Stephen Breyer IIRC.

Ha! She was incredulous that he had to go buy his own robe.

Speaking of Paula being incredulous, her back-and-forth with food author Michael Pollan (“In Defense of Food,” etc.) about the merits of Ring Dings was seriously funny.

You’re all wrong. The single greatest moment in WWDTM history was one word from Paula Poundstone

It was during the “Not My Job Segment” featuring Tom Hanks (which is actually a pretty enjoyable listen in its entirety). You can listen to the whole segment here; the exchange I’m talking about starts around 11:30.

For background, this was not too long after Poundstone had a well-publicized run-in with the family court system in California. Her timing with that reply, and the deadpan, matter-of-fact way she delivers it is just genius. I particularly love the couple of millisecond pause while everyone processes the “joke,” followed by gales of laughter.

This week’s show was a standout for me-- Simon Amstell was hilarious.

…which is my second-favorite moment on WWDTM. I run hot and cold on her stand-up, but she’s got a pretty quick wit. When she works herself up into a frenzy of righteous indignation (or incredulity) she’s very, very funny.

I believe Penn Jillette did that - offered his own voice on the answering machine, or offered to enlist any of a number of celebrity buddies.

Call me naive or optimistic, but I’ve always assumed that even when the contestants lose, Carl still records his voice on their answering machines. :slight_smile:

funniest show ever. not just on radio!

Paula said something once about fruit being ripe for like two hours and how she had to get the kids up at 2 AM because the cantaloupe was ready to eat.

Last year, as I was sitting there watching yet another laugh-free episode of Saturday Night Live, I thought that I regularly laugh more at Wait, Wait, Car Talk or even Prairie Home Companion.

I think that might have been the Michael Pollan episode as well.

Damn, beaten to the punch! I, too, remember Penn doing that.

The couple of times that I’ve gotten to speak to Penn (and Teller) they’ve been a bit standoffish. Penn seems like a bit of an odd combination of really nice and complete jerk, simultaneously appearing to be highly pretentious and utterly without pretention . If he likes you, or even if he doesn’t know you, he can be extremely generous and friendly, but he won’t tone down his persona for anyone, nor will he pretend to be the least bit interested in you or in what you have to say if he isn’t. (Unless you’re Jerry Lewis, that is!)

For those who don’t know, here’s the Jerry Lewis thing:

[spoiler]On his podcast a few weeks ago, he told one of the best stories I’ve ever heard on the subject of hypocrisy, and challenged his listeners to come up with a more hypocritical tale. Some time ago he was standing in the hallway of some tv studio chatting with some fellow comedians, and the topic of Jerry Lewis came up. All the other comedians started talking about how much they admired Jerry Lewis, and how honored they’d been when they got a chance to meet him, and what an influence he’d had on their careers. Penn ripped them all a collective new one, saying that they were all suckered by his celebrity and reputation, that Lewis was mostly a hack, that he’d been good for a few minutes of a lengthy career and mostly due to Martin, etc. As he finishes saying this, and the rest of the comedians are meekly conceding that he might have a point, a door at the other end of the hallway opens and in walks Jerry Lewis! Without pausing for breath, Penn immediately and without any irony whatsoever starts falling over himself to tell Jerry the he’s his idol, that as a little kid he always wanted to grow up to be just like him, that he’s been a huge influence and that it’s such a huge honor to get to meet him . . . and then turns around and sees all the other comedians staring daggers at him.

Obviously, Penn told it much better than I did. For the rest of the show (and the next one) he kept asking his co-host Michael Goudeau hopefully whether any listeners had sent in a story that could top it, and seemed genuinely torqued that no one had and that his self-assessment as the most hypocritical douchebag in history stood unchallenged.[/spoiler]

I remember Penn & Teller on an iteration of Hollywood Squares some years ago. If you remember how that show worked, the host would ask the chosen celebrity a question, the celeb would answer, and then the contestant had to agree or disagree. For Penn (Teller mostly stayed out of it) it seemed to be a game of giving the wrong answer, and almost bullying the contestant into agreeing with him. He seemed to be challenging the players to look him in the eye and say “you’re full of shit”. (“I disagree” in HS-speak.)

Magicians are liars. (Penn may have been where I heard that.) Part of P&T’s act is to demystify what happens on stage, but it seems like he takes that lying attitude off stage on occasion. I can kind of see a point to it. Just because he’s on a stage inside a giant tic-tac-toe board doesn’t mean he knows what he’s talking about. Stand up for yourself and say what you mean. He might even appreciate being told he’s full of shit.

Pears.

It’s funny because it’s true.
Fucking pears.

The lightning round question about Amelia Earhart had me in stitches!