The Press Box - Ep. 100: 'Keepin' It 1600' With Jon Lovett

Episode Date: April 28, 2016

Jon and Dan are joined by Jon Lovett, a former speechwriter for President Obama, to discuss Trump’s triumph in the Northeast (6:00), the Cruz-Kasich alliance (8:00), the beginning of the "veepstakes" (16:00), Clinton's potential progressive VP options (22:00), the science of writing comedic speeches (28:00), and the best moments from Obama's White House Correspondents’ Dinner appearances (33:00). Learn more about your ad choices. Visit podcastchoices.com/adchoices

Welcome to Keepin at 1600. I'm John Favra. I'm Dan Pfeiffer. And today we have a very special guest. Mr. John Lovett is in the studio. Lovett was a speechwriter with me in the White House. I'm Dan. I hired him way back when. And more importantly, we're talking today about, we're going to ask him about the White House Correspondence Dinner, which is the dinner each year where President Obama goes and gives jokes to a bunch of Washington elite. It's a real useful, worthwhile event. I like it.

Hey guys, I'm on the podcast. There it is. There is. So we're going to be talking to love it soon about that. But first, we'll talk about the week in politics. And we're also, we should tell you all that we're taping this on a Tuesday before the primary. So, you know, we don't, we, we, it'll be a little delayed. You probably all listening to this on a Thursday.

Congrats to Hillary, though, on a decisive victory. So if all the polls are wrong and the demographic geniuses at 538 are wrong and Bernie Sanders and Tate Cruz have a great night, then this will just become the Dewey beats Truman of podcasts. It'll be great. I'll put this one in the archives. Okay. So what has happened this week so far? we have a um the the the ted cruise john casick alliance um where so basically what's happened is this is

sort of a a shoddy deal here um as as we've mentioned before in this podcast indiana is a critically important state uh i think if donald trump wins indiana it seems like no one will be able to stop him if ted cruise wins indiana you know there's there's a good possibility trump doesn't get to 1237 on June 7th, the day of the last primary. So Ted Cruz and John Kasich made a deal where John Kasich said he would not compete in Indiana. He would not have put resources into the state if Ted Cruz decided not to compete in Washington, no, in Oregon and New Mexico.

It's really, it's so funny that John Kasich making a deal to not compete somewhere. Like, that's a deal he made with the voters. Like, you know, oh, if you want to win Indiana, yeah, I guess I won't try. It gets worse than that because Indiana is winner, well, the winner of Indiana gets, I think, 20 delegates statewide or 37 delegates statewide. The rest of the 20 delegates are proportioned by which congressional district you win. So it makes sense for a case, like, you know, Cruz benefits a lot more from this deal because in New Mexico and Oregon, it's proportional the way the delegates. So it's not like, I don't think Kasek really wins from this deal. I don't know, Dan, what do you think about this?

I mean, the whole thing is ridiculous. But, you know, but like Kasek, Cruz was like, you take Oregon. Kasek isn't even, didn't even make the voter guide in Oregon because he couldn't get his shit together. So it's like, Kasek is not in the voter guide. You know what? That is a real disservice to his voter. That's a, that was easy. I mean, I don't know.

So Trump had a great response to this, as Trump often does, which is he framed this as the system is totally rigged. He said, when two candidates who have no path to victory get together to stop a candidate who is expanding the party by millions of voters, it is yet another example of everything that's wrong with Washington and our political system. That's actually, you know what's funny? You can start to see, like, like, he's like the Trump is learning. He's adapting. He's testing, he's like a raptor testing new parts of this. offense.

Because like, that was a little, that was a little worked over that sentence, you know? Yeah. A person who's not a moron helped him work on some part of that. So I skipped over a parentheses in that sentence. Oh, oh, no. When he said, a candidate who's expanding the party by millions of voters in parentheses, all of whom will drop out if I am not in the race. So he added, that's, there's his character.

There, you can't stop it. He can't help himself. Can you imagine the Donald Trump, Paul Manafort editing process now? He just hands him speeches and Trump just starts to. Don't you just assume the Trump editing process is like a scene from Madman where he just like dictates to some person typing. Yeah. He's just like who he calls the girl. That's right.

So Dan, do we think this helps or hurts Trump? I think it, I don't think it hurts. It certainly doesn't help John Kasich. So let's establish that back. I think he, this feeds right into Trump's overall message, which is clearly working. in a couple ways. One, when you see these polls, it's pretty clear voters believe a person who gets the most delegates in votes should get the nomination, which is a crazy idea. And then, and the other part is Ted Cruz, his appeal at the beginning of this process and throughout was he was not the establishment candidate.

And now he has basically adopted the establishment position. He's actually adopted a member of the establishment as part of his alliance here. Like a little brother. Yes. And so had they done this a month ago with actual resources from actual functioning super PACs, they have been able to keep Trump under 1237 by picking off some districts and places. Here, it seems like a little too late. And I'm not sure anyone really knew what they were doing.

The case that got asked about this earlier this week, and he refused to tell us supporters to vote for Cruz. Yeah. He can't bring himself to do it. And well, and Cruz this morning said that, and said the same thing. He's like,

well, people should still vote for me in those states. Well, I feel like this is something that was hatched between John Weaver, who is KSik's chief strategist and frequent star of the circus on showtime. And Cruz's campaign manager, Jeff, they, like, hatched it over beers and forgot to tell their candidates.

And Kasek generally feels like he's the last person to learn about everything his campaign does anyway. He's the last person to learn what America does. It's like they just wake him up for a nap to do the debates and let's put it back to bed. He's going to be the last person to find out he only won one state in this entire process. Speaking of which, Trump finally has a nickname for John Kasich, one for 38, Kaysen. That's brutal. A little on the nose.

It is so, it is so pathetic that these guys couldn't get their act together to do half a deal until late April. guys like where are these people been living it's it's unbelievable there it's so the I mean what what Trump got right is so someone someone did an interview with some with some voters about this deal and one woman was like I'm really disappointed in Ted Cruz that he partnered with the establishment on this and you know what I never did trust Ted which is just like I she must have been a Donald Trump plant but I thought that was a great quote. There are like 8 million Donald Trump plants.

The country is full of Donald Trump plants. That's what we've been discovering. I would like to see a poll that like just test the awareness of the term lying Ted. Because I bet it's incredibly high. So that, I think, go ahead. If you did a Roar Shark test and just like ask people like, what's the first thing that comes to anything of Ted Cruz? I bet lying Ted is near the top. Yeah, but that might have been true in like October of 2013.

Well, they might have just called up dishonest. wouldn't have had the clever nickname of Wy and Ted. With an apostrophe. It's a patchwa. So we will see if this, I mean, here's the truth about Indiana is it is not like, it is not like New York. It is not like Pennsylvania or Maryland or any of these states that Trump, you know, should be doing well, we'll have done well in after this week getting like over 50%.

The polls are relatively close. Trump is ahead in Indiana. but A, there hasn't been that much polling. B, it is a state that's not a perfect match for him. So Cruz is probably thinking if he can pick off a few percentage points here. I mean, in some of these states that don't seem as good for Donald Trump, Cruz usually underpoles what is eventual performances. Kasek does worse than the poll show, almost always.

Which is wondering if you can get negative numbers. Right. It could be a fairly close race in Indiana. And, you know, if Cruz eaks it out or comes close, he can then say, look, this deal helped me get there. Yeah, I don't really, other than becoming a member of the establishment, which seems like a real problem here, Ted Cruz, in the very specific vacuum of Indiana, if he could get one or two points and win that state, that's probably worth, you know, in the risk-benefit analysis, that's probably worth it for him. And are they sort of counting on the fact that this isn't about messaging or what reaches voters in terms of them hearing about the deal, but it's purely a calculus based on what happens when resources are moved around? You know, like, this isn't about anyway. It's a signal to the super PACs.

Right. But more specifically, it's not about voters knowing, oh, hey, cruising Kasek told me who to vote for in each of these states. I should listen to them. It's more the resources not being there will lead to more cruise support. Yeah, I think that's right. Right. Right. It's a message to John KSik Superpath, which has been hurting crews everywhere to stop doing that. Do they have Wi-Fi at the John KSik Superpack? Will they get wind of this? Just some guy in a basement.

He like, he like takes the tinfoil hat off me like, am I needed? Is it my time to shine? All right, we have high opinions of this deal I'm keeping it 1600 Let's move on to the Veep Stakes The Veeb Stakes are here It has happened, it's started The New York Times told us so Yeah, it's true

So there was a New York Times story That the VEP Stakes We're just using the word now You guys are just saying Unironically You're just saying Vip Stakes You just say it like What's new with the Veep Stakes

No Reject It says right here in my outline in Veep Steaks, so I'm just going to say it. We were going to say the vice presidential nominee selection process, but that seemed like a mouthful for the pot. Anyway, so there was a New York Times story that said Hillary Clinton has begun her search. And it talked all about, you know, what she's looking for in a vice president. And it started naming some names of possible candidates.

Two responses to this New York Times story. One from our old pal, David Axelrod, who said, said that it was a story leaked, you know, purposefully by the Clinton campaign to sort of start pushing Bernie Sanders out of the race, or at least let everyone know they're no longer worried about Bernie Sanders and they're moving on to the vice presidential search, aka the Veep Stakes. But, and then Jennifer Paul Mary, the communications director at the Clinton campaign tweeted, you know, as they always say in campaigns, those who those who don't know talk and those who know don't talk.

Did I paraphrase that right? Those who talk don't know, those who know don't talk, right? I think that's what I said, love it. Didn't he say it wrong? Dan, Dan, he said it wrong, right? I got to side with my fellow pod host, too. We'll find out. I don't care.

We'll learn on Twitter whether I got it wrong or not. He got it wrong. So, what do you think, Dan? I have to side with Paul Mary on this one over acts. I think having been in this spot on a campaign. Dan wants a job in the Clinton White House. That's right. Like all of the Bernie Bros in my timeline, I'm just hoping to get paid by the Clinton machine.

It took me about to figure that one out. I don't think, this is not a story you want. The Clinton campaign has been very careful, like, in there to not overplay their hand in saying it's over. Right. And they've been trying, part of this is like to build a bridge to get the Sanders supporters on board. And it's just like, what an annoying distraction to spend the next like four. days of your life debating whether you're actually picking, you know, like who's doing the vetting, you're picking DeVal Patrick, are you picking Julian Castro? Like, you know, that just seems like

it's not something you want. Now, I will say this, that when we ran in 08, because Barack Obama was on the scene, we didn't have this massive universe of former advisors and allies. Like basically every person in, like I believe, I don't think Patrick Healy, who's a good reporter, made it up. I think a lot of people who were purportedly close to the Clintons in some way, shape, or form talked about this at some cocktail party somewhere. Isn't the thing that it can both be true, both what Palmer said and what Akron said be true? Yeah, yeah. I think it's probably true that, well, first of all, if you do, if you go through the story, there's some quotes that are from campaign advisors who are unnamed, which means that that means people in the campaign did it. And then there's plenty, there's plenty of quotes from Democrats, Democratic allies,

close to the Clinton campaign, which literally could be any Democrat who lives in Washington, D.C. Yeah, I mean, that could be, I think the intern from, like, 2004. I talked to, I forgot. I talked to Healy. I'm in the story. So, like, the Clinton allies thing, I think is just fascinating because, like, it literally, you're right.

It could be anyone. Like, if you were to get on the metro in D.C., half people in your car would technically be Clinton allies in some way, shape, or form, or people who periodically advised the Clinton campaign, which is a don't. the one you get a lot, which is like, if you send an email to like Robbie Mook or Podesta, like you periodically advise the campaign, even if they don't respond. This story has Lady Linda Rothschild all over it. No, but I mean, yeah, don't you think, Dan, that it's possible that the campaign could have said,

all right, we want at least, it's, Patrick Kelly's doing a story on the vice president's research. Let's not participate too much, but it's not bad to have a headline out there that we're looking ahead to sort of send a signal to Bernie. And then the story just sort of got out of control because everyone's very time. I mean, it's one of these, it's like a prisoner's dilemma of source, which it starts. And so you're like, well, he's not writing the story. So we guess we better do something. And I am sympathetic to the Clinton people because they, you know, it's like in their view,

in the Obama campaign, we could like not talk and like literally in a way and no one would talk, right? That would just be it. They could find no one who was, there were no Obama advisors who did not work for us, right? And the Clinton campaign, it's like if Palmary or Pedestor or someone on the campaign doesn't say something. It's just like it's going to be a story filled with quotes from random deputy staff secretaries from the Clinton administration who are offering their thoughts on, you know, whether Tim Cain is a viable vice president or not.

Right. Like at a certain point, Healy had a list. And there was a question. And that list being accurate becomes a question they have to answer, right? Yeah. But the truth is, like, I would bet with the exception of maybe four people on that campaign, no one knows what that list is. There may be a list of people that they may think about, but like in 08, we basically had, you know, almost like it was such a tight process that 99% of the people had no idea what was true or not.

Yeah, including the speech writing operation, which had to write three different speeches for three different possible vice presidential candidates and go through that entire deal because no one would tell us who it was. Do you still have your Evan Buy VP nominee? speech written by Ben Rhodes. I think he had Evan Byrd and Adam Freakle had Tim Cain. I feel like you should post those on media or something. And then I forget, I wonder if I think I just did, I think I worked on Biden or someone else didn't. I don't know what was happening.

I think I was working on the convention speech. Yeah, way to like pull rank there. Yeah, well, I'm not going to, I wasn't going to write the Evan Buy speech. We should note for our, we should note for our listeners right now that, that Dan Pfeiffer used to work for Evan Buy back in the, that is a fact. That is a second. Take a good journey. We'll never know what it was like.

I believe he was quoted in the New York Times story too, wasn't he? Evan By was, yes. Yes. I mean, he's actually a pretty good source fist because he's been on the DP shortlist for like three consecutive presidential cycles. Always a bridesmaid. He might be the most vetted human being alive. What a time. So, no, it was a very, so yeah, it was a very closely held process in in 2008.

Dan, you were, I'm guessing you were probably part of it. Like, only in the sense that. I would, like, go into Pluff's office and I'd ask him questions, and he would just stare at me, and I'd have to interpret his stares as to whether things were true or not. David, blink once. It's like, yes, if Tim Kaine is actually an option, blink. And, you know, and at the end, I think, if I remember this correctly, we all knew some, like, group of, very small group of us outside of, like, Pluff, Axe, Pete Rouse, Bob Bauer,

knew that the list really was by Tim Kane and Biden were like the three eventualities. We were preparing rollout plans for and you were writing speeches for and all of that. And so it's like we weren't confirming that was the list, but we weren't waving people away. Yeah, we were, yeah, except we weren't waving away. And we were trying to, and it's always hard. Like you're in this tough position where people call them like, is this the list? And even if you deal with this in the Supreme Court thing too, which is you're hesitant to, you don't want like them to pick a person who's not on your list to write about because if that brings you like a bunch of political blowback, that would be damaging. But then also like months of scrutiny on the person who your choices like can limit the nominees eventual decision making process.

Oh right. If it becomes a big firestorm. And so in a way, we had like this is probably a bad thing to admit. But towards the end, when people were really zeroing it on the three, and the press coverage was getting crazy, this rumor started that Chet Edwards was on the list, the congressman from Texas, who was like the head of the Veterans Affairs Committee. And like, we were, Chet Edwards, yes. Our goal is Vice President Chet, like, who wouldn't want that? And like, we decided. quiet again for a while.

I'm not going to interrupt you again. Dan, I promise. I'm done. You have a specific section to this podcast that you can't wait until we get to. And am I? We did not. I'm not. Oh, sorry, you go.

All right. I'm going to hang up now. They, and so the press, someone reported that Chad Edwards might be on the list. And we just specifically did not deny that. And I remember like all this press flocking the, Texas to try to like stake out Shed Edwards to see if he was about to become our VP nominee and it was like a good

like look shiny object over here you guys look at that to give a little space because people like tracking the movements of our people and I remember Mark Amender former National Journal reporter now podcaster like would you

whatever that website that tracks plane tail numbers was tracking all the planes leaving Chicago and going to Indiana Delaware and Richmond to see if we could find any private planes going to pick up the VD They accidentally stumbled on a rendition. Meanwhile, Joe Biden took Amtrak right up to Springfield. No one saw the guy in aviators just sitting in quiet sitting in the quiet car.

So should we irresponsibly speculate about who it's going to be, Tim Cain? Yeah, absolutely. I think we should think about who, I think we should use for Hillary Trump and Cruz. Sorry Bernie Sanders and John Kasich. Yeah. Cruz is lucky we're doing it for him. Right. Who they should pick and who they probably will pick.

And so let's start with Hillary. Okay. Who do you think she will pick and who do you think she should pick? I'm going to go Tom Perez on both. A friend of the podcast. Give me a break. You're like morning Joe over here. You show up.

He loves you forever. We'll see after today if that's true. Love it. Yeah. Oh, he's talking about me. I thought he was talking about, I didn't realize he was talking about me. No, I also think, well, I was to Eric down in my head. I think Sherrod Brown's a good one, too.

I don't think Sherrod will do it. I don't think he wants to. But I think, I'm in the camp that she does need someone, or she should pick someone. I'm not going to say need. She should pick someone fairly progressive that will, you know, make the Bernie side of the party very happy. And that's Sherrod. That's Tom Perez.

That's Elizabeth Warren, though I still think that's pretty far-fetched. I love the Elizabeth Warren idea, though. I know. Dan, you had that. You talked about that last week. I did that. I fired off that trial balloon last week.

I think the problem with Elizabeth Warren and Sherrod Brown is Republican governors. But isn't it in Massachusetts, don't they go to a special election? They will go quickly. They will. So it would just. locally again.

Yeah. Right. I mean, we're going to go ahead. Probably won't lose that one twice, right? So, like, obviously because he was on our podcast, I think she should pick Time Perez. And I say that because he was on our podcast, but also he is a, he is a strong progressive. I think he would obviously, I think he's a good foil to her on the stump.

I think she will pick Tim Kate. I think that is like the decision-making process will everyone want to have their idea and it will boil down to the lowest common denominator. And I think Tim Kane is great. I think he'd be a very good vice president. He would have been a good choice for us. But it's sort of like- He was close.

Very close. I think he was right after Biden. Yeah, exactly. So he beat out Evan by. I mean, that's not, I guess that's not saying a ton. So why do you think that's a safer bet? Because it's, I think the mentality will be. I don't think it is extra safer bet.

I think conventional thinking will make you think it's a safer bet, which is like, here's a white male senator from a swing state and we don't lose the Senate seat if we went. Like, so that just seems like the old way of thinking. I think he's a pretty good, you know, he's fairly progressive. What you're saying is personified by the Clinton campaign. Well, not using a Senate seat is going to. It's a real thing. And there are a few elections where it's going to be more, it's going to be harder to know in advance how much. of an effect that would have.

You know, we just don't know right now what's going to happen with the Senate at all. It's just we have no idea with the ramifications of having one of these two oddballs at the top of the GOP ticket. Right. Okay, so that's Hillary. Cruz. I think Cruz should, I mean, Cruz should pick, like, the most likable human being alive, right? Like, if you could get, like, Steph Curry or Taylor Swift, that would be, like, the

ideal thing. He needs like the ultimate. I think he would end up. So because they're unavailable, Carly, yeah. Tom Hanks won't do it, right? Maybe. Who knows?

Pretending to Liza Cruz would be an Oscar-worthy performance. So the... It's like talking about volleyball. The more relatable volleyball than take this. The, I think he would end up with Kasek would be where it would go. Rubio would not do it. K-6 just seems like someone just told him to show up in Cleveland to accept the nomination. We're like, okay, that's fine.

Happy to be here. Why am I here? Let's get to Trump because this is the interesting one and probably more likely. I have no idea who it's so tough to have to match Trump with someone and to imagine someone running around with him, like trying to make the case for him. So I have three paths Trump could take. Okay. One is establishment, send a message to the party that, and the elected officials that you have a, like one of their own has made it. Which he has said he wants to do.

That's the, that's the hint that we've got from Trump. Right. So that's like Kasek, Cruz, I'm sorry, Kasek, Rubio, Christy. I don't think there's a chance Rubio does it. Kasek maybe he'll just be convinced. And Christy, I think, actually probably actively wants it, which is why he's. allowed himself to be just absolutely embarrassed for the last two months here. So that path, path one.

Path two is he could just go bad shit crazy, right? Typical Trump path. So that's like Sheriff Joe Arpaio, Sarah Palin, something like that. And then third would be. Corey Linowski. Right. And third would be outsider serious, which could be like, Carl Icon

I would bet I think the smartest play for Trump in that world would be like a military person like you know not that I know to have any other do it like Stanley McChrystal

or David Petraeus or some very serious person did Jim Van dey just call into this podcast? Yeah that's right we'll get to that in a second can we get their names

off the innovation party Jim Van de Hai we're talking about the editor of Politico who in the Wall Street Journal basically called for a military Hinta funded by Cheryl Sandberg and Mark Zuckerberg. We would tweet out this. We would tweet out this op-ed, but it's behind the paywall, and we don't want to make America

stupider. So it's, if you happen to have a Wall Street Journal subscription, don't read it. But I think, like, this is actually basically a plotline from the latest season of House of Cards, but it would be to find some disaffected military general who thinks Obama hasn't gone after ISIS enough, right? And that's like, and that would give people some faith that's like, oh, you know, there's someone, you know, it's like, it's like a more extreme version of Cheney to Bush. Yeah.

What about a, I think, what about a woman? Do we think Trump goes with a woman for, to match up with Hillary here? Like a, like a Joni Ernst or Nikki Haley. Nikki Haley. She seems like she wouldn't do it. Well, whether or not, no one's ever said no. That's true. It would be at first, but I mean, this may be the first person to just say absolutely

flat out no to, but, but, I mean, she would help him in every way that he's the worst. Chan Brewer. Jam Brewer. That would be amazing. Sending a real signal. Okay. What were you going to say, Dan? Do you have a pick on who you would think he should pick?

I mean, I think like a, what about Rudy Giuliani? Oh, interesting. I can't have him get a suit on. I mean, you know he wouldn't say no. That's right. He's well known. Well, what he'd say is 9-11. Wait, actually, can't they not be both from the same state?

Yeah, they can't. Oh, right. Trump would have to, like, change a citizenship to Florida or something. That's right. Or his registration of Florida. Right. Isn't that what Cheney did that, didn't he? Yeah, he had to fly back to Wyoming and secretly registered a vote.

You know who's just crazy enough to say yes? Jim Webb, Democrat, Jim Webb, who said he preferred Trump over Clinton. That's a superb idea. Then he's got the, like, look, Republican Democrat unity ticket. That's actually, I mean, it would be amazingly insane, but on paper, it's a pretty good idea. And then she picks Tim Kaine. what a weird thing the most boring vice president

debate in history the Jim Webb thing just made me nervous in my stomach let's move on to the White House Correspondence Dinner where we'll interview

our so far quiet guest John Lovett glad I'm going to finally have a chance of participate in this podcast so Lovett I've never really asked you many personal questions

in life because you're my next door neighbor How did you So one thing everyone should know about it is before he was a political speechwriter He actually dabbled in stand-up comedy Can you tell us how you? Contrary to his performance on this podcast, that is true How did you get into comedy?

When did this happen? I graduated from college and I moved to New York And I was thinking about being a lawyer And so I was paralegaling during the day as a temp And then because I was a temp, they didn't really have me do anything So I would like fill out my law school applications. And then at night I would go to open mics around New York and just try out doing stand-up.

And I ended up doing it a fair amount. Did people come? How many people were there? Well, so there was there anyone in the crowd? So the open mics are filled with all the people participating in the open mic. So that's a fun group. And then I also ended up doing a bunch of these bringer shows where they would let me have stage time if I convinced enough of my friends to go and pay the cover and buy two drinks each. and then I was sort of at the stage where I was still doing these bringer shows,

but I was running out of friends, and it was time for me to either decide, like, are you going to go on the street and hand out cards, you know, or are you going to just do the open mics, or are you going to give up? And I chose to give up. That's good. So when was the first time that you were writing, speech writing for a politician, and someone said, hey, we need jokes.

Is anyone funny? Can anyone write a joke? So I was a, like a junior press person for Senator John Corzine of New Jersey. and somebody reached out and said that Hillary Clinton was speaking at a roast for Barbara Walters. And I had just submitted a writing sample to become her junior speechwriter. And so it was this great thing that actually ended up putting me over the edge and getting me a job there. But in the meantime, it was a strange thing. I hadn't been hired.

I hadn't really heard that they were going to hire me. And they asked me to come write jokes. And so it became this incredibly important audition. and so it was me and a couple people in in Hillary land writing jokes for her to make fun of Barbara Walters. And she ended up skipping the roast. She couldn't make it for votes, but it got me the job. Oh, that's good. I'm trying to remember what.

Dan, do you have a question for John Levitt? So, so many questions. They don't want to ask me questions because they know me. We're going to try to stick it to yes, no here. So you have written and helped write comedy speeches for President Obama and for and for Hillary. Right. And what is the difference? What difference?

Like Obama is, I think, probably most of a grade more naturally and more natural comedian than Hillary. So what's the difference between writing for the two of them and how, how did, like, what's the path to make Hillary Clinton funny? That's a great question. I remember we did she, Hillary did the, then Senator Clinton did the like New York State correspondence dinner once. We went to Albany. We did this video. And actually, we should pull that video because Donald Trump is on that video saying he

wants to be president. And nobody's discovered it yet. Wow. But it's a, uh, find that video, people. It's, you should find that video. It's pretty, it's the, uh, we, we did it in like a day. So I'm not saying the production values are where I would have wanted them to be where anybody would want them be, but you make you.

But it was pretty funny. I think that the, look, I think the answer is always to not try to make the person seem like someone they're not. I think it's been really fun writing jokes for President Obama because he has this, he has this kind of great detached air about him. He's in on the joke. Right. And I think, I think with Hillary, she's a little bit more old-fashioned and a little bit

more of kind of an earnest nerdy joke teller. And so I think it's less about like kind of like commentary jokes and more sort of hard, old fashion, like monologue style jokes, I think works the best. Yeah, we sort of, we've learned that Obama does really well joking about sort of the circus of politics. Right. Because he doesn't like it. Right.

Right. And so those jokes. And jokes that you wouldn't think would work for a typical politician because they're not like set up punchline, but they're a little different, have worked for him. I think the best example of that, which we should tell the story is the 2011 correspondence dinner. Yeah, yeah, yeah. When we, uh, when he took down Donald Trump, apparently temporarily. Um, real fatal blow. Yeah, exactly. But what, lo, why don't you tell the whole story of that dinner? Because that's, that's, I think, all of our favorite, our favorite, uh, correspondent's dinner moment. Yeah. I mean, we, we,

so first of all, we had written a, a different, a dinner. speech, I believe, because we had done a whole lot of, it was before the birth certificate was actually released to the public. Right. We had worked on a whole speech. But we knew the birth thing was in the news. Yeah. So we were going to make a bunch, and we knew Trump was going to be there.

So we had this whole, a bunch of jokes we were going to tell about the birth or thing, about Trump, saying that, you know, the president wasn't from here. We had a lot of jokes like that. And then I remember you came over to our office and we're like. Dan, because Dan called me. Right. And I remember I was thinking, like, what are the, we, we, we set it out loud because it was so crazy and it was going to be such a problem. Like, could you imagine if today's the day they're going to release the real birth certificate?

Because then we'd have to rewrite this whole thing. And Dan, do you remember my reaction when you told me about this? You thought we were fucking crazy? No, I was also really pissed because I was like, are you, like, here was this big moment where the president was going to have his long-form birth certificate flown out to D.C. so we could present it before the nation at a press conference. And Dan was like, you know, I should tell you that this is happening because it might affect the dinner. And I was just like, are you fucking kidding me? This is the worst.

We have to rewrite these jokes. Dan's like, okay, there's bigger things at stake here. This is like a summary of all of our conversations of real world news where you got super upset, not because of like, whatever the big problem was, but because it affected the speechwriting process. Yes, that was it. I had one thing in mind. So then we had, I think there was a Wednesday, wasn't it? And so we had two or three days to rewrite the speech and to rewrite any parts of it that were related to the birth or stuff and Trump.

And I think it actually ended up making it better because it really forced us to take what we had and make it work. And I think we had the vague idea for that Simba video. And then we decided like, let's make that the intro. Let's have him come out. So did the Lion King video. Oh, no, no. That's when we had the I'm a real American. Yeah, the whole Kogan song.

And then we were trying to figure out what we were going to do about Trump. And I think it was, I think I talked to Jud Appetow about it. And then, and that was like, that was, we just talked for like half an hour just sort of writing down ideas and jokes. And it ended up being, Judges sort of ranting about how ridiculous it is that people take Donald Trump seriously that led to this great joke about, uh, celebrity apprentice. Yeah, celebrity apprentice. Which was. And, but the reason that. that joke was interesting is because I remember you got off the phone with Judd and you were like,

all right, it was a very long, like, six-minute riff on Donald Trump and the Celebrity Apprentice. And it was like, you know, oh, I'm actually going to have it here because I'm going to read it because it's just, it's one of my favorite. For example, no seriously, just recently in an episode of Celebrity Apprentice at the Steakhouse, the men's cooking team did not impress the judges from Omaha Steaks. And there was a lot of blame to go around. But you, Mr. Trump, recognized that the real problem was like, lack of leadership. And so ultimately, you didn't blame Lil John or Meatloaf, you fired Gary

Busey. And these are the kind of decisions that would keep me up at night. Well handled, sir, well handled. Was it funny that for that joke to happen, there was like, I'd say a solid 45 minutes to an hour where I'm just reading through the synopsis for episode after episode of Celebrity of Frontis, which was a dark moment. I remember I saw that and I said to you, like, I don't know if Obama can do this because it's such a non-traditional joke. It goes on for a whole paragraph like this. And we brought it to him and he was so happy. Yeah.

And he did right on the spot, he started delivering the joke to us. And it was so funny. It was so funny. In the practice session. He says Gary, Gary Busey. Gary Busey. The, but yeah, and it actually changed the way we did those speeches. It's changed that speech and it changed, I think, the way we think about them

overall we've kind of ever since been more willing to give him much more subtle jokes that are better on performance actually is that the is that the same year with the Mitch McConnell joke is that that was that was that was a couple years later but that was the same idea which is there every every John I were talking about because we were reading through the the old speeches and just going through them first of all we make the same CNN joke every year and I don't think we should stop and I don't think and and and you get ready guys um but um but um We, every year we managed to get in one or two jokes. That's not even a joke that's just Obama yelling at the press in a funny way.

Or yelling about somebody. And the one about Mitch McConnell was people are always telling me, why don't you get a drink with Mitch McConnell? Why don't I get a drink with Mitch McConnell? Why don't you get a drink with Mitch McConnell? I'm just yelling at people. But the press soon realized they were like, that wasn't a joke.

That was just him being angry. Well, it spawned like several more ring down columns about Obama's unwillingness to play the Washington game. Right. And didn't, didn't Mitch McConnell take a picture with he had a beer and he gave Obama a glass of red wine. Yeah, it was pretty well played, I thought, on his part. That's good. Yeah, I mean, if you believe in those kinds of, you know, gender heteronormative drink choice norms. I thought he invited him to drink some bourbon in Kentucky.

Yeah, but the photo had a glass of wine. Because Obama is in a feat. liberal, which, you know, fair enough. There are, reading through the old dinners, though, there are certain jokes that repeat themselves, like the color of John Vayner's skin. Right. We had a couple of years. And then we did two years in a row.

We did jokes about Michael Steele in the Heazy. And then he did it again the next year. And the president ad-libbed in line me. Like, I do this every year. He goes, it's okay. It still works. He ad-lubs very well up there. He just kind of like, he doesn't ad lib entire jokes, but he throws an aside at the end of the punchline when he knows that it's going well.

Yeah, I mean, I don't like it when he adjusts the wording on the fly. Like we did, like somebody did make a choice here about how to phrase these jokes exactly. You know, you don't have to stick to the script. You won the votes, but let's sort of remember that. That person is on this podcast. It was me. You leave the country. We'll do the jokes, right?

I think for, I think there are a couple things on this. One, it'd be, you know, I, what I think is interesting. that we learned the first year working on this speech was it's a White House Correspondence Dinner. It's theoretically a political dinner. It's theoretically filled with politicians. But jokes that are very insider politics tend not to work because like 50% of the room is celebrities to reduce the year because Republicans have told him to go and it'd be a cool way to get pressed.

Right. There was a, I think it was either the first year or the second year. We did a bunch of jokes about Politico. Yeah. And it was really gratifying because a sizable portion of the. audience did not get it at all because they don't read or know about Politico. Right. But it was really fun for us.

It was great. Sometimes we just write for ourselves. It sometimes we'd be the joke that killed and literally like the gap, the big bang theory was just like, what are you talking about? Right. But we did get to watch the political. I was at the political table night here and the look of pain on their face was gratified to me personally.

So thumbs up. And that was the last time you were invited to the Politico table. That's right. I think also it would be interesting for you guys to talk. about the process for writing the speech and the roles that people inside and outside the White House play in it. Love it as the joke writer-in-chief, do you want to walk through that process? Well, yeah, what do we do?

So we start... All flattery here on keeping 1600. This is not what it's like, you know, I don't really listen to this podcast, in part because I get exposed to the podcast in real life on a basically daily basis, but it's not usually this nice. So we start by gathering jokes. Well, actually, no, we first have a conversation. It's whoever's going to be involved in the speech.

Me, John, Aksarod, Dan, you're part of that. Tommy Vitor's a part of that. Cody Keenan's a part of that. When David Litt joined the White House, he became part of that. And we start brainstorming joke areas, video ideas, just very, very 30,000 feet. And then we start writing jokes. And we reach out to comedy writers. is we reach out to political people that consider them something funny, some of which do that correctly,

other which just want to participate and everybody gets a turn. But we start collecting as many jokes as we can. And it's interesting, you know, a lot of people want to help. And every year a different, you know, it's through the grapevine, a different famous comedian or celebrity or joke writer will kick in their jokes. and even the best people struggle to find the right tone for this. I think that like the really, really funny writers who are not of politics, they write a bunch of great jokes,

but they're not appropriate. And then I think a lot of the political people that submit write a bunch of appropriate jokes, only a couple of which are funny, which is fine. Everybody writes a bunch of, you know, it's all about writing far more jokes than you could ever need. But then we end up collecting hundreds of jokes,

hundreds of jokes by the time the whole process is over. And you're whittling that list down and you end up with a list that I think has somewhere between two and three times as many jokes as you'll need. Meanwhile, at the same time, you've narrowed down any audiovisual stuff you want to do, whether you're going to be a video or a slideshow or some other thing that requires some advanced work. And then you basically get those two things to the president. We sent him a long list of the jokes we're going to use and a couple of. couple ideas where we're at with the video, and he'll go through and say, I like this, I don't

like this. President Obama usually, he'll cross out a couple that he's like, nice try, guys. That's not happening. Usually because we have failed to recognize that this isn't the most important thing he's going to do. And probably the correspondent center shouldn't be something that puts like peace talks at risk. Well, interesting, interesting story there is the year of the Trump fiasco. It was the day of the dinner. So it was Saturday and Lovett and I

and David Axford were supposed to meet with the president one last time to go over the jokes. And we get to the Oval Office. We're standing outside and the door's closed and his personal secretary at the time Katie Johnson said

you know he's on the phone with the general in Afghanistan you're going to have to wait we have to push the meeting back and we're just like oh my God we're going to get to the hill. Don't you understand? It's the day of the dinner. We don't have time to make changes. We have to do a walkthrough. This is unbelievable.

So finally, we, he lets us in. Well, no, but wait, before we get let in, we're standing out there and there's a very serious man from the National Security Council who's there because he's in charge of making sure the calls are kind of sort of doing the logistics for the president speaking to a general. And he has a very serious look on it. Like he's focused on something. And we say, oh, this is the perfect person to show our videos to. And so we make Katie pull up on her computer. The Lion King. The Lion King thing and I think a couple other things. And we start showing this very serious person our comedy. And he's not really laughing. And so we just sort of chalked it up to his bad mood.

So then the president lets us in and he's like, hey guys, you know, all the jokes are great. He's smiling. He's happy. Tossing a football around. Yeah. He's like, all the jokes are great. He goes, there's one punchline where you're talking about. You're revealing that action.

the Republican candidates in 20thel also have, you know, non-American roots. Wait, so the joke was, we had a joke that, you know, Tim Palentis run into some problems with the base because they found out about his real name, Tim Osama bin Palenti, right? I would say it was a B-plus joke. It was fine. It wasn't a string of them. You guys, Michelle Bachman is from Canada. We did, like, a whole bunch of them.

So, President's like, I would just use someone different than Osama there because I think it's been played out. I think it's an old joke. Everyone talks about bin Laden. Like, who cares, you know? He's like, I would use some other bad dude out there. Like, try, try Hosni. Hossi.

And then we were like, that's not funny. That's not as funny. I mean, but we were so relieved that he didn't have very many changes to the rest of the speech. In hindsight, because he was focused on something else. And that's something else we later learned was the general that he was on the phone with was General McRaven. And he was talking about the order he had just given to kill Osama bin Laden. Catherine Kill us on a lot. And he didn't want to joke about it at the dinner.

And the other thing is, if you remember, the president asked us to add... God bless our troops. Keep our troops. And to a section on the troops in the serious part of the end of the dinner. And it was like, okay, you know, for some reason, he sort of wants to do that this year. He's done it before. You know, it's not a strange thing, but it wasn't necessary strictly. That was our favorite story.

Love it. Do you have a favorite joke from all the years? Oh my, that is a, do I have a favorite joke? You know, I am still, I love when we get the opening right. I love when we land on like the perfect joke that just kicks off him speaking that's like confident and very simple. Like I still like one, I think it was one of the first jokes we ever that he did, maybe the first joke he did, which was on Barack Obama. Most of you covered me. All of you voted for me.

And it just set the tone, it set the tone for how he was going to be at these dinners. I love that joke. I'm trying to think of others. That was one of my favorites, too. Dan, do you have a, do you have a favorite one? The one I will always love is the Celebrity Apprentice joke. That is the favorite. I watched that speech again in preparation, in my rigorous preparation for this podcast every week.

And when you watch that and like the way president took down Trump and then you like turn off the, you put, you know, So I watched the video when you watch the news. You're like, holy shit, that guy is about to be the Republican nominee. It's a pretty amazing thing to imagine. One other joke I really liked was when he was talking about how it was either the first or second time at the second term. And he said, you have to admit I'm not the strapping young Muslim socialist I used to be. I was really happy with that. You know what I just saw that I really liked is I'm also hard at work on plans for the Obama Library.

And some have suggested that we put it in my birthplace, but I'd rather keep it in the United States. is a typical joke, but then he goes, did anybody not see that joke coming? Show of him, only Gallup, maybe Dick Morris. Right. Because it was right after the 2012 election when everyone called it right. That's right. That's right.

I also like the one from, I guess that was last year when I don't have it in front of me, but it was like some people have a bucket list. I have something that rhymes with bucket list. Oh yeah, the bucket list was good too. It's great. It's great. Some good times. All right.

That is all the time that we have for today. Flew by guys. It flew by. Thanks, everyone. As usual, this is keeping at 1600. We're on Channel 33. You can follow us on iTunes, Stitcher, and SoundCloud, and also tune in on Mondays on HBO Now, HBO Go, and HBO On Demand to see after the throne. I thought Andy and Chris did a great, great episode, great first episode this week. Yeah, they were awesome. They did such a good job. So tune into that. See you next week.

Talk to you soon, guys.