The Daily Beast Podcast - How These Comedians Turned MAGA Men Into Laughingstocks

Episode Date: December 24, 2020

Rudy Giuliani tried really hard this year soil himself: the hair-in-the-can, the Russian agent pal, the presser by the sex shop, the buckets of conspiracy drool. But it wasn’t until he got caught red handed with Borat’s daughter that his reputation was smeared fully, finally, and forever.  The hand-down-Rudy’s-pants incident was one of a whole bunch of different ways that political comedians rammed into Trumpworld in 2020. Matt Wilstein, The Daily Beast’s resident comedy guru, breaks down the highs and the lows with Molly Jong-Fast and Jesse Cannon on a special crossover episode of The Last Laugh and The New Abnormal podcasts. From Jordan Kleppler’s head-first dives into the maskless hordes at MAGA rallies to the viral impressionists who took over your Twitter feeds, Matt, Molly, and Jesse break down the funniest moments, and answer some of the biggest questions as we finally leave this hell year behind: What does Sarah Cooper do if she can’t channel Trump? How did Balire Erskine manage to become Tiffany Trump’s bestie? How does Kleppler prep to make unintentional comedy with MAGAmen? What was up with Jim Carrey’s impression of Joe Biden? Was Saturday Night Live ever really funny? Ever? For more great political comedy, listen to The Daily Beast's The Last Laugh podcast. Hosted on Acast. See acast.com/privacy for more information. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Hi folks, it's Rick Wilson, and welcome to The Daily Beast's The New Abnormal. Hi, I'm Molly Jongfast, a left-wing pundit, and editor-at-large at the Daily Beast. I'm also an editor at The Daily Beast, a former Republican political strategist, best-selling author, and full-time troublemaker. We're here to have fun, sharp conversations with some of the smartest people in media, politics, business, and science that help make what's happening in the country and the world clearer. I'll try to keep Rick to the minimum number of F-bombs and try to keep our... kids, pets, and other wildlife sounds from invading our respective bunkers. Matt Wilstein is the senior writer for The Daily Beast covering the intersection between politics and pop culture, as well as the host of The Daily Beast, The Last Laugh podcast. Hi, Matt Wilstein. Hi, Molly. How's it going? You know, trying not to die. It's good. Can I say that on the podcast? Yes, I can say that on the podcast. We're all trying not to die. Yes.

Everyone's trying not to die every day. That's right. That's what it's all about. So talk to me about political comedy. It's been a year, hasn't it? For everything, but for political comedy, absolutely. I mean, I spend a lot of my time at The Daily Beast watching and writing about and interviewing people who do political comedy, whether it's the late night shows or, you know, really anything. But it's just, it's been a pretty crazy year, but I think the one thing that's really like stood out to me above everything else

is this like kind of new-ish form of aggressive confrontational political comedy that's come out this year. And, you know, thinking about Borat, obviously, is sort of like the big one, which I know you quite enjoyed the Borat sequel, right? I love him, and I love that he targeted Michael, well, really Rudy Giuliani, but also Michael Pinnis. Yeah, Michael Pennis, yes. Yeah. So, yeah, I mean, I'm just a huge Sasha Baron Cohen fan. going way back and I interviewed him on my podcast when he was doing, Who is America, which was

another show that I loved. And then I'm actually about to have, I just talked to him, but it hasn't aired yet, the director of Borat to Jason Walliner, who's just kind of a fascinating guy who's been around in comedy for a long time. But this was his first movie that he directed, which I thought was insane. Because think about that as a first film to take that on and everything that went into it. It took like two years, the whole thing from, you know, start to finish. Obviously the Rudy Giuliani thing was really one of the moments of the year and he had a lot of moments. Put down your cram! She's 15. She's too old for you.

Why are you journey? No, she's my daughter. Please take me instead. Take my annals. Don't want you. No, take my anus. Do not have her. I'm better than him. No, I better. My back pussy very time. No, please.

My friend's an an anew. Please, I will let you enjoy my crumb in your mouth. No, I bet. I was in prison many years, so I have techniques to marry you. I was in prison many years. to my mouth. What's going on here? Look at this guy.

I forbid this union. Rudy, Trump will be disappoint. You are leaving a hotel without golden shower. It's funny because this was what started the downward spiral in some way.

Yeah, it kind of foreshadowed it in a way, right? Yeah, except the downward spiral is what? He's still the president's I mean, I guess the hair in the can dripping down his face was the lowest moment.

I mean, four seasons total landscaping is in my mind it's a battle between four seasons the hair dripping and obviously you know putting his hands down his pants in front of Borat's daughter not great

which is not great yeah I'm still convinced that there was more going on there than shirt tucking in yeah I think that's a general consensus at this point yeah definitely but yeah I think there's there's that there's Borat and then the other one that really stood out to me this year is another person I've had

on my podcast is Jordan Klepper, who has been doing this stuff for the Daily Show for years. He was a correspondent on that show, but then kind of left. And now he's come back just periodically doing these segments where he confronts Trump supporters at Trump rallies in a year where no one was doing that kind of thing, mostly because of the pandemic. He was actually going out and putting on a mask and talking to the maskless hordes at these Trump rallies and getting them to say some really insane things. So I think he definitely wins in my book as the sort of bravest, you know, riskiest comedian who actually risked his life for comedy this year. We are here to celebrate the winning of Donald Trump.

Oh, you're four years too late. Huh? You're four years too late. No, no, no. He won this time. This time? He won. It's not the size of the flag that matters.

It's how many votes you get, the electoral college system. They were here to celebrate the fact that America is a rich. diverse nation with so many different kinds of alleged election fraud. There's people that's changing votes. Who? People across the United States. Where did you hear this? All over.

We can't ignore it. We're talking about having dead people vote, number one. Should Trump have appealed more to the dead person vote? Should he appeal? We just need fairness. Yeah. I mean, I have to say, as someone who's been to CPAC twice now, The first time I was okay, but the second time, I really felt like it's a little scary. I mean, they're not. These people are a little scary.

Yeah, I've never been to CPAC. I've been to Politicon a couple times just like the CPAC's, you know, cool younger brother, I think. Yeah, I mean, I feel like Politicon has more of a mix of, like, normal people. They're trying at least. Yeah, I mean, CPAC is like really the drags. You know, Matt, I thought what was funny with Jordan was you talk a lot on your podcast to comedians. about like the ups and downs of their career, their trajectories. You get these stories all the time.

Jordan kind of had this miss with his show, the opposition, even though I think it had some great moments. But then you see him immediately right after like some people saying that that was a loss for him, come back with this just amazing moment in his career. Yeah, it is. It's crazy. It's like he, I quite like the opposition as well. And it was definitely, it was like one of these long,

there's been a long string of shows that have tried to follow the Daily Show and failed post, Colbert rapport. And, you know, it's Jordan Klepper. It's Larry Wilmore, who I also love. But, you know, just no one seems to really been able to make that time slot work since Colbert left. But yeah, Jordan Klepper, it's like, once he really, like, figured out his thing and focused on it with these segments, and again, it's like, it helps that there's only one,

you know, six-minute segment every three months. When you can do that little amount of work and really pack it in, then it really, it shows had the quality. Yeah, and when you interviewed him, though, he really shed a light, though, on, like, how much the process went into this and how much craftsmen should be went into it, I thought was really interesting. Yeah, I mean, he obviously prepares a ton, because with any of these people who are going out and trying to make comedy with real people, they're basically just, like, creating tons of different scenarios in their head and hoping that they're funny and that it works out. So, you know, I think he would go in with, like, a million different questions

with people, but then he's such a great improviser that he just has to, like, go with the flow of whatever's happening in that moment. And, you know, if it's taking a, you know, taking the piss out of a Trump supporter who's, you know, has some hypocrisy coming out of their mouth because they, you know, believe in, one that I just was rewatching was he talks to someone who believes, who's pro-life and anti-choice, but thinks that it should be, you know, a choice whether to wear a mask. Yes, yes, yes. That's really common in that group.

I mean, it's sort of amazing. disconnect. Yeah. Who would have ever thought that we'd get a bigger disconnect with those people than, you know, big government versus small government and chasing women around and policing their wounds? Yeah. Yeah.

Exactly. Matt, the other thing that you were talking when we were beginning this about is that this was a very big year for political comedy and social media. Yeah. And I think that has a lot to do with the fact that everyone was stuck at home with nothing to do. And sort of production value was prized less maybe than it was. in the past and people were at all just yeah they filmed themselves in their house and yeah i mean i think

obviously the big one in that realm was who the real big breakout star was sarah cooper which i don't know when when were you when were you guys first aware of sarah cooper what do you what do you remember about about that because it was clearly it's like she was nobody and then she was huge yeah i mean i definitely saw her do those videos and they're good felt like one day i didn't know it and then the next day, it was like there was 10,000 videos. Yeah, and then she got a Netflix special. How do you keep doing that? Yeah, I mean, that's a big question.

How does she pivot from doing lip-sinking Trump is, I think, will be a hard thing for her career? Because I don't know if you guys saw the Netflix special, but it was like a lot of Trump, but a lot of kind of experimenting with other stuff, too, and I would say some of it work better than others. But she's already started putting out videos where she's actually speaking in her own voice. Like she did a great one. She's playing a character, which is Jenna Ellis's law mentor. Oh, that's great.

That's a really good idea. Yeah, that's a really good idea. So she's kind of like, you know, imagining what sort of the people behind the scenes are in this insane MAGA world. But again, like, I guess I don't think MAGO world is going to go anywhere, really, anytime soon. So I think if she wants to keep working in that realm, she can. Yeah. Who else did you see doing interesting things? I mean, the other breakout star for me, who's, I think, a lot less well-known than Sarah Cooper at this point, but is also just amazing, is this woman Blair Erskine, who does these also just ridiculous videos.

And I think it's even like, it's more difficult than what Sarah Cooper was doing, because she's actually creating original stuff and creating original characters, where she's spoofing, again, MAGA people like anti-maskers. And she did, I think one of the, one of my favorites was she was playing Tiffany Trump's, best friend in one, which I thought was pretty funny. Tiffany's like my best friend. We met like three months ago at this club I used to work at Jacksonville. And over the weekend, she was like, hey, do you want to come to my dad's house? We're having, what does she call it? We're having a coup. And I was like, sure, you know, because I grew up poor. I've never been to like a rich person party. And I was like, I'd love to go to a coup. But we've been here for like five days and the coup has not happened yet. And like, um, the stuff that has happened is like pretty, I don't know,

like not okay. Oh yeah, that one was so good. She came out of nowhere. She's like, you know, I was looking at her IMDB just to be like, I wonder if she's done anything else. And like, no, she's done, you know, some short films or some random things. And I think maybe she's been in a commercial or something, but she's, she's really just someone who was at home during this time, started making videos on her phone and totally blew up. And now when she posts them, it's like they're highly anticipated, get shared all over Twitter. I know everyone at the Daily Beast gets excited and watches them the second she posts them. So it's pretty crazy. Yeah. No, good for her. Yeah. Yeah. I think it's interesting too because you're seeing,

especially I became like addicted to political TikTok this year. And never did I think that I was going to be in awe of 18 year old's political humor. Yeah. What was something on from an 18 year old on TikTok that got you? And if you say George's daughter. Out of respect to common new abnormal guest, George Conway. I will not say Claudia Conway. She is quite, she's quite beautiful. I mean, I think, and I found her funny, but I don't, I'm not a TikTok connoisseur, so I don't know. Was she trying to be funny?

I'm not even sure. She's just a pretty funny ones. She's pretty funny. What of the best ones to answer the question was, was she did a TikTok of her mom coughing when she got COVID. That was. No bad, but hilarious. Like, it was like. some of the best gallows humor of the year.

Oh, my God. I mean, she's kind of hilarious, but yes, it's true. I know. Where is she going to go next? I think she could have a big future, Claudia Conway. Yeah, I could see her ultimately ending up being famous, but again, for what? You know, it's good to have something you're famous for. Yeah.

Instead of just who you are. Yeah. So another thing we were going to talk about is the biggest staple of comedy of the last half a century, Sarah Alive. Yeah. It's been also a very weird year for Saturday Night Live, which is something that I am just weirdly obsessed with, as anyone who knows me knows. And for no good reason. I think most of it's pretty bad, to be honest with you, and yet I watch every minute of it

every week. We're very glad that you're on that page because Molly and I were discussing this beforehand, that we were both like, uh, Saturday Life's a little rough. Well, hey, you talk to Alec Baldwin, so. I mean, can you explain, has it always been bad? Well, the thing that everyone talks about this is like Lauren Michael's thing is that everyone thinks that when they were in high school it was the best that it ever was. That has more to do with their sensibility when they were in high school, I think. Just like people's favorite records.

It's always the record that you've really felt at 19 years old. Yeah. And that's like, it's totally true. It's like for me, I'm like, yeah, when it was Mike Myers and Dana Carvey and Chris Farley, it was the best. Like, that's just when it was the best. Yeah. I don't know. Is that true or is that someone else might have very.

different perspective on that. It's funny because it's like there's clearly, occasionally they hit it out of the park and those clips become huge viral sensations. Yeah. I mean, what I say to everyone who's like, should I be watching SNL? I'm like, no, you should be watching whatever the one clip the next day is that we often post on The Daily Beast is what was worth watching and otherwise, no, sitting through the whole thing is definitely not necessary. But, you know, their political stuff, I think, always gets attention because it just becomes a thing no matter what it is and you know i think it's Tina fay as sarah palin is obviously one that that stands out and i think that was that was like an example of something that was funny but it was more because sarah palin was so funny than anything

tina fay was doing it was she was she was just verbatim repeating the you know ridiculous things that came out of sarah palin's mouth but 30 rock is really funny yeah and third but that's you know she was that was she was writing it and she was like yeah but that was born of SNL. Yeah. Yeah. And it's sort of the, the SNL behind the scenes

in her, you know, exaggerated way. And I think that's also one of the things of what SNL stays relevant through is that the things

SNL spurs are truly, truly some of the most amazing stuff we've ever had in comedy, whether it's the really popular stuff on to just the obscure stuff.

Like, you had Robert Smigelot and TV Funhouse is my favorite thing ever. And I think triumphed in some of the best political comedy of the past few years

as well. Oh, yeah. Yeah, yeah, definitely has. Yeah, he's great. It definitely is a thing that they do come up with some brilliant stuff, which is why it's still known as such a big thing. Don't you agree? Yeah, and I think the other thing, I mean, this kind of goes into the Tina Fey thing, because when she was playing Sarah Palin, she had already left the show, so she was kind of one of these earlier celebrity, you know,

guests coming in. And so, and then with Alec Baldwin playing Trump, he basically became a member of the cast over the last four years, which is something he probably never thought he would do. And then they've just kind of kept trying it again and again. Like, you know, Ben Stiller, who we talked to back in the day, was Michael Cohen, and that was really funny. And, like, Robert De Niro was Robert Mueller. And then I think they jumped the shark a little bit this year when they brought in Jim Carrey as Joe Biden, which to me just really didn't work at all. As great as Jim Carrey is, I just didn't see it in his impression that it was really. Yeah, he was terrible.

Like, it just, it wasn't funny. capture what was funny about Joe Biden, if there is something funny about him, which I don't know. Well, unlike President Trump, we do accept the results of this election. We're not mad at them. We have to act graciously in victory, though. We need to go forward together. Unfortunately, there are situations in life, and this is one of them, where there must be a winner and... user. Are they keeping him on?

So no. This past week, they officially replaced him. First, Jim Carrey did this like very kind of tweet that got a lot of attention that I thought was like strangely sincere where he was like, I'm stepping aside as Joe Biden, like I've done my service and now's the time for me to leave. So luckily I think he saw the writing on the wall and also didn't want to be Alec Baldwin for the next four years going to SNL all the time. Like I think he has better things to do.

deal. Yeah, but Alec Baldwin, as Trump, is really good. Yeah, he is, he is good and he's more Trump than Trump at this point. Yeah, I think, and it was a larger than life impression, which is what you need sometimes, and especially with someone like Trump, you know, I think having a big celebrity, you know, made sense in that way. With Joe Biden, I just, I think they, they tried it with Jim Carrey and it didn't work, but now they have one of their actual cast members, Alex Moffitt, who you might know Molly as the S&L's Eric Trump, who's quite funny. Oh, yeah, yeah, yeah.

I don't know if you've seen those, the thing they do with Don Jr. and Eric, I think, is actually very funny, and they often do it on Weekend Update. Yeah. Where they'll come on, and Alex Moffitt plays Eric as this, like, as, you know, the dumbest Trump son, and is basically just looking, looking over to

Don Jr. and mimicking all of his movements, if you watch him and just like, anyway, it's very funny, but he premiered his Biden, and it's not like it was the funniest thing ever, But it was, it was like a pretty accurate impression. And I think it's great that they have someone from the cast doing it and there to do it. Because they just, they haven't had that, you know, for the last four years in these big roles. And they already have Maya Rudolph in as Kamala.

And she's great, but also someone who's, you know, not from the cast. So one, she can't be there all the time. And two, it does kind of take away the opportunities from these people who are, you know, supposedly the main cast members on the show. Yeah, I mean, I guess. But the goal here is to make the show really funny. And, well, it is, I mean, being on SNL is a huge opportunity. And if you don't get, you know, out there.

I don't know. I don't have so much. But I guess, I guess that's a point. Yeah. I mean, they've had some really good cast members on this season two doing political stuff, like, you know, Kate McKinnon, who does everything amazingly. But she really took off as Rudy this year because she had a lot to do as Rudy. and then, you know, they've had some other great people like Cecily Strong.

She did Melania, who I feel like she hasn't done Melania in ever in a really long time, but I feel like she got one-uped by Laura Benanti who does Melania on Colbert's show and is unbelievable. And it's like I kind of think she's done it to a degree that no one else can quite get there. It's so funny because Melania herself is so, you know, is basically just a parody. Yeah, well, that's the problem is that they're all parodies. You know, you could say that about any of these people. I mean, and I think, like, if we do talk about what are good moments of Estenelle past our teenage years, the Sean Spicerimitation was one of the great.

Yeah, that was one of Saratelai's best moments of all time. Yeah, I agree. Yeah, Melissa McCarthy. And that was like, that also kicked off the women playing men in Trump world, which apparently he really did not like. That was the story that came out around then was that. Yeah, that was great. great. He didn't like that women were playing his people. And so then I remember there were a lot

of talk about like maybe they should start having a woman play Trump for that reason. Yeah. No, that was really great. But is there not a thing to that like, there's part of me that thinks Biden is a little hard to characterize because it's all in the speech. Like, it's hard to do him. Yeah. And it's, I mean, I think this has got a lot of conversation around this during the Obama years too, was that they had a lot of trouble making Obama funny. And like famously key and with the anger translator were the only ones to really find a good angle on Obama. But yeah, Biden is, Biden is not, I think it's, it's tough. It's, it's going to be hard. You could if you sort of weren't committed to it. The problem with Trump is, Trump is so awful

that you really do hate him, which adds an element, you know, no one is ever going to say, like, you know, don't be too me. You know, it's harder when you're the guy who's like, kind of saved democracy for now. also think there's like that thing where there was, they may have been a little careful leading up to the election because of the stakes and that once, once Biden is president and now, I mean, there's a little bit more freedom to be harsh because, you know, he's, he already beat Trump. Yeah. Yeah. In fact, now that you say that, it's funny because like, I think the only good Joe Biden pressure I heard was when episode one did that episode where it was three Joe Biden's talking to each other. And they don't care if he gets elected. Yeah, you're allowed to be funnier in that sense. Yeah, I mean, I remember also with Will Ferrell's George W. Bush, there was like all this talk about how he made Bush more likable, even though he was playing him very dumb.

He made him likable to a degree that people were willing to vote for him and that there's like this theory out there that he actually, because he seemed more fun than Al Gore, both in real life, and mostly on SNL, that that actually influenced the election, which I don't know if I believe that, but it's possible. It's a theory. Yeah, certainly, certainly, yeah, theory. Anyone who works for us in L likes to say that, you know, oh, no, no, we don't have,

they don't want to be responsible for elections for deciding elections. Yeah. Yeah, like having Trump danced the hotline bling. Yeah, well, that's a whole other thing when they had Trump posts. That was, that's the, you know, original sin of political comedy at this point. Yeah. Thank you. so much, you know, for coming on. This was really great. Thank you guys. Stay safe. Happy

holidays. On that note, we'll wrap up this episode of the new abnormal from The Daily Beast. In future episodes, we'll be talking with smart folks from The Daily Beast and beyond from media, culture, politics, and science who will help us understand what's happening to our country and the world. We hope you'll subscribe to us on your favorite podcast app and share the show on social media. We're just getting started and don't want you to miss an episode. If you'd like to follow us on Twitter. I'm Molly Jongfast, and he's the Rick Wilson. Thanks so much for listening, and we'll see you again on the next episode. Want more great listens? Check out our comedy podcast,

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