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By: Josh Gondelman, Liz Hynes, Greg Iwinski and Sasha Stewart

In part 2 of our series on protecting free speech, veteran late night television writers Josh GondelmanLiz HynesGreg Iwinski and Sasha Stewart join us to discuss the eventful past few months in the world of late night, the current state of the genre, and how they think late night comedy might shift throughout the ongoing fight to protect free speech.

Josh Gondelman is a former late night writer for shows like Desus & Mero and Last Week Tonight with John Oliver, a stand-up comedian and former WGAE Council Member.

Liz Hynes is a writer on Last Week Tonight with John Oliver, a former writers’ assistant on The Late Show with Stephen Colbert, and a member of the WGAE Council.

Greg Iwinski is a writer known for his work on late night comedy shows like The Late Show with Stephen ColbertLast Week Tonight with John Oliver, and Game Theory with Bomani Jones. He previously served on the WGAE Council.

Sasha Stewart is a writer whose credits include the late night comedy show The Nightly Show with Larry Wilmore, the comedy series Dying for Sex, and the documentary series Amend. She currently serves as the WGAE’s Secretary-Treasurer.

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OnWriting is a production of The Writers Guild of America East. The series is produced by WGA East staff members Jason Gordon, Tiana Timmerberg, and Molly Beer. Production, editing, and mix are by Giulia Hjort. Original music is by Taylor Bradshaw. Artwork is designed by Molly Beer.

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Transcript

Josh Gondelman: You are listening to OnWriting, a podcast from the Writers Guild of America East. In each episode, you’ll hear from the union members who create the film, TV series, podcasts, and news stories that define our culture. We’ll discuss everything from inspirations and creative process to what it takes to build a successful career in media and entertainment. I’m Josh Gondelman, WGA East member, former late night writer and stand-up comedian among other things, and I’m joined by veteran late night TV writers, Liz Hynes, Greg Iwinski, and Sasha Stewart.

It’s been an eventful few months in the world of late night and today, we’ll discuss the current state of the genre and how we expect/hope/fear it might shift during the ongoing fight to protect free speech. I’m so excited to have this wonderful panel assembled to talk about late night comedy writing and late night comedy television, and its kind of prominence in the current battle over free speech going on. So I would like real quick for everyone to kind of introduce themselves and talk just for a second about your experience working in late night, and let’s start with Liz, please.

Liz Hynes: Thanks Josh. I am Liz Hynes, I currently write for last week tonight with John Oliver. Before that, I was the writer’s assistant on The Late Show With Stephen Colbert. So late night has always been my point of entry to every job I’ve ever had, The Nightly Show with Larry Wilmore before this, and I think it’s just one of the best ways to kind of see every single part of the industry working together. And I feel like the exposure I got even as an intern on a late night show was more comprehensive than any job I’ve ever had since and probably ever will again.

Josh Gondelman: Amazing. Thanks Liz. Greg, could you give the listeners a little introduction to who you are?

Greg Iwinski: My name is Greg Iwinski. I started writing late night TV at Second City and iO in Chicago and then started in television at The Late Show With Stephen Colbert where I met Liz and then moved to Last Week Tonight With John Oliver. I wasn’t there the same time as Josh and met a bunch of people who had written on The Daily Show and Larry Wilmore, which is how I met a bunch of people, how I met Sasha, and then I wrote a sports late night show with Bomani Jones and then did some cartoons and things like that. And I only say all that to introduce how it is incredible how small a world it is for how outside then it gets a full podcast episode when it is such a small chunk of people.

Josh Gondelman: Thanks Greg. Yeah, for sure. It is a small world and I feel like people really do meet each other and get to know each other, especially in New York. Sasha, can you give listeners a little intro to you and your background?

Sasha Stewart: Hi, I am Sasha Stewart. I got my start in late night as an intern at The Colbert Report where I then worked as a PA and a graphics researcher and helped developed a script writing software called Scripto. I worked there for about five years and we actually ended up taking Scripto to Last Week Tonight to The Daily Show to a bunch of other late night shows, and so I actually got to know a lot of people through that process.

And then I got my first writing job on The Nightly Show with Larry Wilmore, and then I have since worked in other places that were not late night, but also I worked on a couple other sort of, let’s call them all late night style shows. So remember when Facebook Watch was a thing, I worked on a Facebook Watch show that was late night style. And then I also worked on a Netflix show called The Fix with Jimmy Carr, that was a late night style show.

Josh Gondelman: Oh, right on. I hosted a Facebook Watch.

Sasha Stewart: It was a moment.

Josh Gondelman: It was a moment. Okay, this is great. I’m so grateful to you all for taking the time to be here, but let’s just start with everybody. What is to you the value of late night comedy shows and what do they bring to the current media landscape overall? What’s unique and special about late night?

Liz Hynes: I think that late night is especially in a time with kind of nonstop news that everyone’s getting bombarded with. You don’t always have time for a narrative to calcify, and I don’t mean this as in the government hands a narrative and then these shows say it, which is the allegation currently. But I mean it in a sense of it is helpful for society to have some sense of shared reality.

And I think that these late night shows are often the first place that narrative calcifies and you see a show that is not just one person at a desk. It’s many people who have been grappling with and shaping how they feel and what they think makes the most sense to present this information to a bunch of people in an audience and billions of people who are watching it online and the next day. And I just think that it is a really helpful cornerstone in the sense of a shared reality for society, and I think that’s valuable as those stones are being eroded every day.

Josh Gondelman: Yeah. Cool. Thanks Liz. There’s so much there.

Greg Iwinski: I think that societally, even outside of this moment, something that’s so important for late night is it lets you, whether it’s for the first time or it’s about news that just happened, be incredulous without being cynical. And that specifically means I feel like late night writers now ask one more question when someone goes like, “Well, I didn’t hear that.” It’s like, “Okay, well, would you listen to it right now then and tell me what you think about it?”

Just asking any politician on the Sunday show one more question than what they’ve answered. I think it’s true with even outside of politics though that there are so many movie trailers and show pitches and keynote speeches where you think there should have been one comedian in the background, just kind of proof testing what you’re saying because one of us can sit there and blow the whole thing up with a mean question.

And so whatever pop music is coming out or what movie is big or a big food trend or a cool app or something happening just in youth culture or whatever, having a place where we can make fun of it and poke at it and go, “Well, that kind of doesn’t make sense or that’s weird.” Or, “Why are we doing that?” That isn’t just what is kind of the bottom level, which is just be cynical and say everything sucks, that I think is valuable. You need a place where the A student class clown goes, not just the F student class clown.

Josh Gondelman: I love that.

Sasha Stewart: Yeah, I think it’s a great way of holding our leaders accountable. It is not the news way, it’s not the dry way. It’s a funny, smart, interesting way so that people who want to relax at the end of the day, who need to unwind, who want some catharsis can get that catharsis while also feeling like, “Yeah, wait, what is going on?” And like Greg said, “Being able to question authority, being able to question what’s happening in the world and being able to help them understand what’s happening in the world in a funny, relaxing way as opposed to a way that brings them terror.”

Josh Gondelman: Yeah, I think it is so valuable for all those reasons, and I think it’s not valuable in that it is informative and helpful, but also an enjoyable way to process things that might not otherwise have a lot of good feeling within them and behind them. So these kinds of shows late night, but also other kinds of talk shows we were talking about the network shows, whether it’s Kimmel and Fallon and Seth Meyers and Colbert and John Oliver of course and The Daily Show, but also morning shows that kind of tackle the same topics like The View. And they really, it’s not new that they’re in kind of the crosshairs of Donald Trump himself and the Trump administration, but it really came to a head and went to a new level this summer and early fall. Why is there so much focus on clamping down on this kind of television?

Liz Hynes: I have a really rudimentary response to this, which is that I don’t think Donald Trump has had a normal conversation in his entire life where someone was not fawning over him. And I think that just seeing people have with varying degrees of productive conversations about you without you or one of your stooges in the room is incomprehensible to him that he could be the topic of discussion and it is not flattering and so many people are watching and he can’t control it. I don’t actually think a lot of Trump is much more complicated than that. He’s not a master schemer, he’s not a smart man. He’s pure id. He’s a child in a withering body, and I think that at the end of the day, he needs someone in the room if he can’t be there.

Sasha Stewart: There’s a reason why the term is petty dictator, and we’re seeing that play out right now. He’s so petty, and I actually think that these attacks when they are stood up to show how weak he is, because a real leader, a strong leader can take a joke. Somebody who believes that they have power doesn’t need to worry about a comedian making fun of them. They don’t need to worry about people having a lively discourse on the view about them.

They don’t need to worry about these things because they understand that they have a position and a role in our government to play and that they’re going to do that job and at the end of the day, then they’re going to leave and do another job. But of course, that’s not how dictators think. They think they need to be loved, they need to be obsessed over, they need to be fond over like Liz was saying, and I think that anybody who stands up to them is then seen as a threat.

Greg Iwinski: To put a less fine point on it, these people are losers. And I mean in the sense that Donald Trump would call them losers. They’re not cool. They don’t have good ratings, they’re not nice to look at or listen to or be around. They’re unpleasant losers, and what they’ve done is orient their entire lives in the United States government around forcing people to tell them that they’re cool, and that’s why you see this push towards culture because is Pete Hegseth a cool soldier?

No, he’s the guy who failed Ranger school, got divorced, cheated on his mistress with a third woman he yelled at in a hotel, Kash Patel nobody going anywhere. Lindsey who’s doing the new prosecution and the DOJ has never prosecuted a case, they’re all losers who have had a goal that they failed at and have been mocked by the cool people, and it makes them furious. And so now they have one goal, which is to make everyone cool say they’re cool too. And that’s why you see in soft power way and small and hard power way like one using the FCC to try to muzzle speech, but even in soft power ways like saying, “We’re all going to a Starbucks and making them put Charlie Kirk’s name on a Starbucks cup.” That’s us showing we have power, that means we’re cool.

It is loser behavior top to bottom. In the ’90s we saw the culture war that was also against late night comedians and other comedians and people who were impure like Howard Stern, and it was rap music that was too dirty and it was all culture that was the problem. And over their entire lifetimes, they haven’t been able to in any way make a dent other than I guess Yellowstone. Congrats. You got one show.

And so now I think what you see in late night coming for us is we are obviously the front of the spear because we’re out there every day doing 250 shows a year on a couple of different stations pointing out that uncool people aren’t cool, and I will say just in the defense of that is that’s always been a late night value. Every president that’s been alive in my lifetime I’ve written jokes about, I was doing jokes about Obama’s drone strikes in a theater full of six people in Chicago, Illinois when I was at Second City. Liz and I have joked about multiple presidents on TV. We’ve all done, but these are the people to whom that joking and not being cool is the most important thing in their lives.

Sasha Stewart: It also points to a deep insecurity that they feel, and that’s sort of what I meant about how they don’t really understand power. They don’t really have real power because they’re so deeply insecure about the power that they do hold. Now that doesn’t mean they’re not dangerous, that doesn’t mean that the threats aren’t real. It just means that the power is only there as much as we are willing to let them have it. And so when people stand up, when people fight back, when Kimmel gets back on the air, it shows that the emperor has no clothes. It shows that he doesn’t have nearly the amount of power that he says he does.

Josh Gondelman: Yeah. So let’s talk right now a little bit more specifically about Disney decided this is a few weeks ago, to suspend Jimmy Kimmel and his show because they found something that he said in the wake of Charlie Kirk’s death to be untoward. And it took a little while, even longer for Sinclair and Nexstar to bring back Jimmy Kimmel. So it was about, I think it was probably four shows that were missed, three to four shows, and then in the face of a lot of public pressure and a lot of people canceling their Hulu and Disney Plus and ESPN+ subscriptions, Disney ultimately caved and brought Kimmel back. They’re in New York right now filming in Brooklyn, and then Nexstar, Sinclair followed suit even in the 25% or whatever of markets where they had been holding out. So how did you feel about it? Was there anything about it that scares you and what about it makes you feel hopeful or encouraged?

Liz Hynes: I think one of the scariest parts was seeing how effective this network of right-wing podcasts is that Brendan Carr was able to push the first diameter to make this happen completely independently of the government. He went on a podcast, he said, “Here’s what I’d love to see. These local broadcasters painting Sinclair and Nexstar as if they’re these mom-and-pop businesses when they’re also major media conglomerations that are subject to his merger approval.” He said what he wanted them to do, they did it as if viewers were rising up and demanding that they do this to Jimmy Kimmel. No evidence of that happening.

I think they got plenty of complaints in the wake of it happening. Don’t think anything prompted them to do this other than Brendan Carr. So I think we’re seeing this really robust extrajudicial network of communication that powerful people can give a directive and lackeys willing to fall in line can immediately do that. And it is then on public pressure because again, we didn’t see amazing opposition from the Opposition Party. It was ordinary people standing up canceling their subscription as Sasha was just talking about. So the pushback thankfully, was just as powerful, more powerful, but scary, that can happen.

Josh Gondelman: And Brendan Carr, just for, if there’s anyone listening who is trying to grasp on his specific name is who runs the FCC currently?

Greg Iwinski: Fun thing about Brendan Carr is when he doesn’t know what to say, he frankly is his verbal tick. These are the kind of things you notice if your job is to make fun of somebody, but his frankly is his pause word and you can just count them as he riffs.

Sasha Stewart: One of the funniest things about this was that Brendan Carr was still at the FCC under Biden. He was then elevated under Trump, and while he was there under Biden, he had said specifically called out late night shows as needing to speak truth to power and be able to criticize the current administration, which is what Kimmel was doing on the night that then now an empowered Carr says that he’s going to take him off the air.

Greg Iwinski: Which I think is a great thing about late night, which is that you don’t have to take bad people in bad faith, so we don’t have to waste the time to go. “Can you believe Brendan Carr lied?” You go like, “Yeah, look, hey, the liar lied, and we have proof he lied.” And you get to skip the step that I think is what holds up so much of this is I think a lot of, I don’t want to say our bosses, but a lot of people at the top of the TV and film industry, and a lot of people at the top of the news media think that the internet is a good representation of where Americans are at.

And so I think that’s why when the Kimmel thing blows up, you go, “Uh-oh, 49 to 48 election, half of our people are really mad.” And then you find out that that’s not the case. If you look at polling now, 24% of Americans strongly approve of Trump, 53% strongly disapprove. That’s two to one. So then when two to one of your customers start canceling, you go, “Oh wait, maybe the boardroom conversation and the golf course conversation I’m having isn’t actually representative of this country.” So that was the thing that made me hopeful was out of the whole Kimmel thing was maybe some of these people realizing, “Oh, the really unpopular guy doing unpopular stuff is unpopular with the people who spend their money with me.”

Sasha Stewart: To speak to the scary part of it, what Kimmel said was so innocuous and the fact that Disney reacted so drastically in such a way that seemed like they were terrified, that is what really scares me because the idea that these companies are giving away their power is really what’s been horrifying about the last nine months to me, that it is not just big media companies that are doing this. It is universities, it’s big law, it is judges.

It is so many people who have real power in this country willingly giving it away because they’re afraid of something that hasn’t happened yet and isn’t necessarily going to happen. The idea that their funding will be taken away or this merger won’t be allowed to happen, God forbid we prevent a merger. But that level of fear was not present in the first Trump administration by people who have real power.

There was a lot of fear in the first Trump administration, good fear among everyday people who were hurt horribly by the first Trump administration, but the people in power who could stand up were not afraid and did often stand up. And that’s what we haven’t seen nearly as much of and not nearly enough of in these first nine months of the second Trump administration. And so what I found really heartening and hopeful about this was that I think it was reported by Marisa Kabas, a great reporter, said that it was nearly 1.7 million people who got rid of their Disney Plus and Hulu subscriptions over the course of six days. That’s incredible.

That is an incredible number, and it shows that people are, like Greg was saying, people are angry. People want to take action, and people want to see other people being courageous and people are willing to be courageous, especially when it’s something as simple as canceling a subscription account. But I know that there were a bunch of big games coming up.

People were like, “Oh, no, I’m going to miss my sports thing.” But that shows that people really were willing to put their money where their mouth is, and that does work, that that did move Disney, that our rallies that we had outside the studios in LA and New York had an impact, that collective action really does work. And I, okay, I’m going to say something that’s a little bonkers.

Josh Gondelman: That’s what the podcast is for.

Sasha Stewart: Okay, great. Yeah, yeah, yeah, you’re right. So don’t actually take me seriously, but I do believe that what we’re seeing now with the Democrats actually having a spine in this shutdown fight is the fact that we won with Kimmel. I think the fact that we won encouraged Democrats that, “Oh, wait, people like it when we fight back?” They’re like, “Oh, I remember this now from 2017 to 2018, maybe I will do this again.” It’s not just that things have gotten so bad. I think it is when people see other people taking action, they are inspired, and I think that we have inspired everyday people have inspired our leadership to start stepping up, and I hope that that happens across the board from now on.

Greg Iwinski: Yeah, I just want to say, I think people are realizing that the bar is moving. My non-comedy friends and people you talk to where you go, what did Kimmel say? And then they watch it and they go, “Oh, okay, and whatever. If it’s factually wrong, if the premises are reached, whatever, it’s not a new show, it’s a comedy show.” And then they think about, “Well, what about Dave said a ton of anti-trans stuff on Netflix for $20 million in a special. He didn’t get yanked.”

Gutfeld said that white people should have reclaimed Nazi as their own N-word on his show as comedy, didn’t get yanked. And also in those situations, the writer’s guild didn’t say, “This shouldn’t be on air.” Or, “We disagree.” The free speech bars have pushed pretty high so that then when you come back down here, it does seem, I think, to regular people kind of ridiculous because he didn’t say something crazier than you hear on TV any other day.

I think that’s probably why people were upset, but something we learned as an industry that I think we haven’t fully churned through the lessons of yet is the power of the audience is moving back towards them as it should. We’re moving away from blind subscriptions towards ratings, ratings to ad dollars to upfronts, meaning you have to make things people like to make money.

All these companies that are no longer showing their subscriber gains as how they’re doing well, they’re showing their profit as how they’re doing well, which means we’ve gone in a full circle as I can tell you the 2023 negotiating committee told the studios many times that we would, we’ve come full circle, and I say that only to say that if people had had to express their frustration about Kimmel through boycotting ABC or Disney, not turning on their TV, that becomes a very murky like, “Well, the ratings were a little bit down.” And then they were up for SEC football on Saturday, and then they were down on this and da-da-da.

It’s not tangible, when you are at Disney and you start seeing $20 a month disappear, a million at a time, that is a real tangible protest that I think now you will see spread out through the future across I’m sure multiple causes and reasons that people will say, “I have an immediate way to use my dollar to tell you I like or don’t like what you’re doing.” This, I think, was the first moment we saw, and I think that American audiences saw, “Oh, we can steer these networks now with a couple clicks on our phone.”

Josh Gondelman: Yeah, and I want to get into the guts of something of things that everyone was kind of alluding to and talking about a little more elliptically. It’s what about this made it such a free speech, flashpoint rallying call in your opinions?

Sasha Stewart: I think it was the immediacy because the difference between this and Colbert was that they said, “We’re going to cancel Colbert in 10 months.” Which is, don’t get me wrong, everybody here on this podcast was real pissed and it continues to be, but everybody still got to see him the next night. And for the next 10 months, the idea that Kimmel was pulled off the air, the no pretense, it was explicitly for a free speech related reason due to an FCC commissioner threatening the license of that network and the affiliate stations, one of whom wanted to do a merger.

It still wants to do a merger that is not technically legal right now, and the other that is a super conservative as last week tonight pointed out so well, many years ago that that happened just in an instant. I think the immediacy, the instancy of it was upsetting to audiences and upsetting to people everywhere and was like, “Oh, this is real and this is scary and we need to fight back right now.” It also did not feel like a foregone conclusion that Jimmy wouldn’t get back on the air. It felt like, “Oh, there’s chaos, there’s confusion. We don’t know what’s going on.” That means we have an opportunity to get him back. And I think that people not despairing about it also made it feel like, “Oh, we can fight back. We can win.”

Josh Gondelman: Yeah, I think to me that is something that is so important to underscore here is that there was, like you said, no pretense other than the FCC commissioner saying, “I don’t like what this TV network is doing, and they better shape up in accordance with my wishes.” And then by extension, the wishes of the president and the whole administration. And so it did feel very much like the government interfering in private speech in a way that is unconstitutional.

Greg Iwinski: Also, I think two feels like a pattern. So the second show people go, “Huh.” And it is popular as much as people say late night is dead, they’re wrong, and that’s just not actually true.

Josh Gondelman: Can you say a little more about that, Greg? Because I think you speak really persuasively about this topic.

Greg Iwinski: Yeah. If by persuasive view mean I text all of you all the time, anytime it ever comes up, but yes-

Josh Gondelman: Persuasively and extensively.

Greg Iwinski: Yeah, there’s this idea that late night is dead, but late night is watched by an incredible breadth of people. I think about my sister, who’s not political at all. Kimmel goes away and she goes, “Oh, he’s funny.” There’s no, “He’s right. He’s left. Oh, he’s funny. Why would a funny guy go away?” And it becomes this obvious thing because it was either AP or Pew, I’m sorry, I remember, but last week had a poll out.

They asked Americans, have you in the last year watched an episode of late night television? Not a clip online, an episode of late night TV? 130 million Americans have watched an episode of Late Night TV in the last year. Half of all US adults have watched an episode of Late Night TV in a year. If 10% of those are watching it every day, that’s a huge number, and then 60% of Americans have watched clips regularly.

Again, we’ve talked about this a lot, and it needs to be discussed in a bigger way, which is saying only two and a half, only two and a half is wild too as somebody who’s made shows that people didn’t watch. Only two and a half million people a night watch this 250 times a year, I guess it’s not popular, I guess late night is dead. Well, there’s a lot of places I could go that if I guaranteed you two and a half million people 250 times a year, that’s incredibly valuable advertising space.

So people are watching it on TV, they’re also watching it on YouTube, which the networks have decided is where our shows should be given away for free. No one here on this call, no one writing a show, no showrunner has said, “Why don’t you give away our whole show for free like you do with Game of Thrones?” Oh, wait, you don’t give away Game of Thrones for free or like NFL. Wait, no, don’t give NFL Football. You don’t give those Amazon games away for free on streaming either.

Like, “Oh, sorry, that new Mark Ruffalo thing that I’m going to watch, he has a hot beard.” Whatever that show is, that’s not giving away for free. You put those where people pay money for them, they have value. You’ve taken our shows, put them somewhere that they’re free, and then said they don’t make money. So those numbers are somehow thrown out the window, even though for most shows, that’s 5 to 6 to 7 million people a night every night.

So now we’re at 7, 8, 9 million people combined. Then you add the clips online, everything else. So people are watching both in any way that we can measure it. Millions, tens of millions of Americans are watching late night TV and in the industry there becomes this conversation about, “Well, late night is dead, late night is dead.” Because I don’t know, it’s not something that you watch if you’re a reviewer for the APV Club.

I don’t know what social disconnect there is, but it’s being watched and it has value. And I think this Kimmel thing is a big example of this backlash doesn’t happen if no one watches the show. And I think to Kimmel’s Point, although he’s gotten more political, Kimmel also made The Man Show. He’s got friends across the board, and to a lot of people, he’s just comedy. Colbert is what? And I love Stephen, I’ve worked there, a lot of us have worked with him, but pretty openly political, but with Kimmel, it becomes a like, “Wait, what?”

Josh Gondelman: Yeah.

Greg Iwinski: I’m sorry, President AOC is going to take Tim Allen’s show off the air. What is next?

Josh Gondelman: These are such great points, and you brought up Colbert, Stephen Colbert, The Late Show. Not only was it announced that Stephen would no longer be hosting The Late show after next May, but that the show would be going away in its entirety, no new host. And they at one point said they were losing all this money making the show. And Liz, you and I have talked a little about this off mic, about what felt kind of fishy about that rationale post facto rationale, and I was wondering if you could talk a little bit more about that.

Liz Hynes: I would love to talk about that. As far as I can remember, that leak happened at least 24 hours after the initial backlash. So it gets announced that The Late show is being retired permanently. There is enormous blowback, and then it’s like, “Well, they were actually losing all this money.” A television show is not a company auditioning to do an IPO.

You can tell that since I used the word audition, I didn’t go to business school, but I know enough to know that we do not measure the success of a television show by this. We’re in the red or we’re in the black.” It’s ratings, it’s award shows. That’s what they talk about at shareholder meetings, that’s what they talk about for your consideration campaigns. We have metrics for this, and much like Greg has talked about how they’re redrawing the lines on where the audience is.

If you want to make the argument that late night is dying, you can say that terrestrial viewership is down, but that is true almost across the board for every kind of genre, the audience has moved. Similarly, you can just draw lines kind of wherever you want, if you want to say that, “Oh, well, this show specifically is losing all this money.” CBS has three CEOs, do we need to have three CEOs? None of whom can figure out how to monetize the number one late night show in television, that feels like maybe there’s some cost-cutting opportunities there, but that’s not an acceptable place to cut, that’s not where they want you to think the line gets drawn.

So I just think everyone should always know that the numbers you’re hearing from corporate are numbers that they massage, if not outright makeup, but it was nebulous enough to kind of poison the well and plant the seeds of doubt for people to be like, “Well, maybe I don’t totally understand what happened at Colbert, but that $40 million is a lot of money.” They did get away with this. And so then with Kimmel, they don’t need to bother with the pretense. So I think that it had to fall in that way so they could make it easier to say, “Who did Trump tweet that he wanted to be next?” That’s who will go next. And we don’t have to make up a reason why.

Josh Gondelman: It was so direct with Stephen. There was him saying on air that CBS News paying a settlement to Trump while the Paramount, Skydance merger was in progress felt like a bribe to make that merger go through more smoothly. And then Colbert was canceled, but remained on the air, of course, for several more months. And then there was this post facto justification that it was losing money. With Kimmel, it was Brendan Carr goes on a right wing podcast, says, “Wouldn’t it be nice if this happened?”

This happens, and Kimmel is off the air that night. And so I do think, right, it felt like they’d accelerated the timeline and the brazenness of how directly this is the government saying, “This is speech we don’t like, and it would be great if it disappeared.” How are you all feeling about the landscape of late night now given these free speech battles that late night has become the terrain for, and how do you feel about the future of the industry?

Liz Hynes: Do you remember back in, let’s say maybe 2017, 2018, the first Trump administration? I think late night, got put on this pedestal that was not entirely earned. And it was a lot of people saying the famous phrase, “You’re keeping us sane.” And these hosts would go out and they would meet people and everyone would tell the host, “You keep me sane. I put you on every night.” And, “You’re saving democracy.”

I do not, and have never thought that that was true at the time. I think maybe some of that is being a little bit retroactively earned. I think it is a legitimate battleground for freedom of speech now. I think criticizing the president has become legitimately dangerous, criticizing US foreign policy we’ve seen people get kidnapped off the street for writing an op-ed, criticizing US foreign policy. There are documented instances now of people being detained for speech, photographer at an ice protest has been detained for over a hundred days at risk of deportation.

And at the same time, Marco Rubio keeps trying and so far failing to introduce the ability to strip people of their passports, citizen or not in response to speech, in response to their very broad definition of terrorism, knee-jerk, scary word. You brought in the definition, anyone who criticizes you as a terrorist, anyone who’s an anti-fascist, anyone who’s an anti-capitalist. If you see the latest national security directive that came out, a lot of people on this call have written things that would fit under that very, very increasingly large umbrella of punishable speech.

So I think you can’t be like, “Oh, but the people getting arrested aren’t citizens.” You should care anyway. But it is so clearly every domino is set up for it to start to apply to citizens, to people who have born and lived here our entire lives, that shouldn’t matter that much. It should be a crisis no matter who it’s happening to. But I do think that people who are regularly, publicly and loudly criticizing the president is legitimately dangerous in a way it wasn’t in 2017.

Sasha Stewart: Something that bums me out is something that we’re seeing across the board in this entire industry industry-wide contraction, which is that as what is happening in feature films and in scripted TV is also happening in late night, which is that when there’s a contraction, we’ve seen this time and time again. The first people who get hit are people of color and women.

And so what we saw in 2017, partially in response to the first Trump administration, when companies found it profitable to fight back and because this was also during the streaming boom, and so more shows were getting made, we saw a lot of late night, really fabulous late night shows being helmed by women and people of color and women of color. And then as this contraction began, so this is before the second Trump administration, I want to say this actually started in about 2022 with the Warner Brothers, Discovery merger.

We saw Samantha Bee get canceled. We saw a Ziwe get canceled. Then we saw Desus & Mero get canceled. We saw all of these really wonderful shows get canceled due to budgetary constraints that were because of things that were wildly outside of the control of the people who actually work in this industry. And the hope that I have is that because this is a cycle, it means it will end, and that in a few years, we will start to get to see hosts of color and women hosts and women of color hosts back on the air and doing what they do best. And how will that look in a few years? Who knows? Who knows where those shows will be or how people will watch them, but I believe they will continue to exist in some form or other, and I hope that we all get to write on them.

Greg Iwinski: Or host them. I will say I am always optimistic about late night, even when that is a minority opinion. I think there’s a pendulum swing back and because I think Liz is, as I say many times with many things, Liz is 100% right. Trump winning broke Sorkin era, liberal white boomers, it crushed everything they thought about what America was and they could not psychically handle it, and they needed other boomers to go on TV and be like, “It’s okay. We are still the good guys. This is a mistake. We’re going to figure it out. There’s going to be one good speech that’s his face gives in a church and it’s going to fix everything like the West Wing.”

And so that pushed late night up both budget and in attention and in value and importance. It went from a 12:30 mindset. If you’re our age growing up of weird Conan stuff that no one’s watching to 11:30, which is like this is so important to really a 10:30 PM. mindset in late night, which was like, “Instead of the news, I don’t watch this after the news. I watch it instead of the news and it’s so important.” And this is me fighting back, me tuning in is resistance and one that didn’t work because he won again after doing a coup. But also, that can’t be almost 10 years later counter-cultural.

If only because all the people making it and watching it are 10 years older. And so I do think we’re going to swing back. I think, one, we need to swing back towards 12:30, which is we’re weird idiots doing a thing you can’t believe they’re letting us do, which also takes a network willing to do that, but I think that there’s a distinct millennial sensibility that’s not in late night right now that needs to be there, which is we are so incredulous. We’re in high school when 9/11 happened or younger. So the idea that the system is broken is not only something we already know, we’re not interested in wasting time setting it up.

All of us have done very long essay political news pieces that have jokes in them. And most of the first act that a boomer would write you could throw out. Did you know that the police have some issues? Historically, they’ve been pretty bad to black people. Yes, we can skip that. I can start a script with, “You know a lot of cops are pretty bad, right?” Okay, good. Let’s go. And we need to be able, from everything from this shutdown fight to should the Dems swing left or to how do we talk about each other aligned to political violence?

We can skip an incredible amount of preamble conversation when Mike Johnson is going on TV being like, “I didn’t hear what the president said.” We can just say, “He’s lying. He doesn’t want to talk about it.” All this anxiety and agita and stress that’s in late night right now of forcing the audience to go, “Can you believe the hypocrisy? “I think there’s a moment where it breaks and with newer, younger voices that are now reaching hosts, level of experience will come a relief of being like, “We all get it’s bad. Now that we’ve all admitted it’s bad, now we can make a comedy show.”

So I’m optimistic because I think it’s going to swing back. Cheaper, weirder, darker, more punk rock, whatever. But I think it swings back to a place that speaks to this moment more. And I love all the hosts who are on TV now, but all the 11:30 hosts got their seats before Trump won the first time. So there’s never been a seat that big that’s been filled to address this moment, and I think that’s something that has to happen.

Josh Gondelman: So I think we have been talking a lot about this from the intersection of our job as writers and our positions as late night writers and former late night writers in intersection with free speech and government. And I think I would like to think about this a little more expansively thinking of ourselves as not just writers, but workers, right?

This is a Writers Guild of America East Podcast, so thinking of ourselves as labor and not just as consumers or people who drive culture and thinking of ourselves as citizens and if not citizens, residents with a vested interest in the health of the democracy under which we, let’s say allegedly live. So what about the way people are fighting to preserve free speech is exciting and energizing to you? And what are some ways forward as people in this fight?

Sasha Stewart: Something that happened to me when I was working on a project from 2018 through 2020 was that I used to always think of myself as a writer who did her activism through writing. And I do think that as coming up as a late night writer, that is a very natural way for us to feel that the way that I am speaking truth to power is in my job and I don’t really need to do it beyond that. And donating to X, Y, Z organizations once a month, and then when I was working on this project, it was called Amend: The Fight for America.

It’s a six part Netflix series about the 14th amendment, the one the Supreme Court pretends doesn’t exist. I realized that the activists who have made so much change throughout history, specifically in American history, because what this was about were just regular people and that they did their activism not just as part of their jobs, but just as part of their lives, and it didn’t have to necessarily be something that they were amazing at. It didn’t have to be their skill set.

Like, yes, of course Ida B. Wells is an incredible journalist, but she was also part of the founding of the NAACP and left when it wasn’t progressive enough. You know what I mean? She also single-handedly integrated a women’s suffrage parade just because she wanted to, not necessarily as a journalist, but just because she was like, “This is something I care about.” And to me it was like, “Oh, right. I need to get involved outside of being a writer and outside of being a worker and just being a human being who lives in this country and wants to make it a better place.”

And so I started just volunteering, and I have found that in my volunteering work, whether it’s for a campaign or in voter protection or with our union being Secretary of Treasury now, we’ve all been council members. It gives you back so much more than you put in. Yes, the work can sometimes be exhausting, but it makes you feel more engaged. It makes you feel more hopeful and optimistic because you are putting effort into it and you get to see that make real change, and maybe the change is small, maybe the change is huge.

Something that I found so inspiring is the Mamdani campaign. Here in New York, people just decided, “Wait, this potential mayor seems great. What if we actually elected him?” And he’s inspired so many people who’ve never canvassed before to start canvassing, which is a scary thing. Canvassing as a volunteer is like, “That’s the big times. That’s the big league. You’re really doing it. Talking to strangers on the street, New York City, are you kidding?”

But people are doing that because they see that real change might be possible and they’re inspired. And I think that the more that we as writers, like you said, Josh, see ourselves as workers, see ourselves as part of this collective, and that anything that we do can be powerful and meaningful. You can write letters, you can make calls, you can get on the street and protest. The best thing that you can do is literally doing something and then slowly building up from there.

Liz Hynes: I totally agree with that. And I’ve been really inspired by people that we’ve encountered, whether it was on the picket line or most recently rallying for Kimmel, people who before we even-handed them a flyer said, “I’ve already canceled Disney Plus.” This is Insane. Kimmel was during the day, so most people were walking on route to work, but the strike was so long that people would stop at all hours of the day to talk.

People were really curious about why we were out there, how many people write most shows. I thought it was just one person writing everything. And just, I think that especially as we’re served a lot of algorithmic slop content, we are supposed to buy into the idea that this is all inevitable and this is all very passive, and we’re not supposed to fight back against any of it. And every time we are actually out there, even just with what we engage with as a guild, let alone other protests, like Sasha mentioned, there is a real desire to connect.

There’s a real curiosity around art and around how we’re fighting back against fascism, against the reduction of everything into content and AI and everything that people really do want to connect over this. And so I’m always happy after having any conversation in real life with a total stranger who is curious about me and I’m curious about them because that is what we’re supposed to believe is destined to evolve out of humanity, and I disagree.

Greg Iwinski: Beautiful. Honestly, I love America. Black people have a deep pain and frustration with America and this deep, deep love because it’s your home. You didn’t voluntarily immigrate from anywhere. And I love America, and I think what this has shown me, one is that across all the great movements of justice in this country, it has shown that the architecture that the founders built as much as they were all pretty bad dudes in terms of slaves and liking me or that I exist, they built a really great architecture.

And so the idea that freedom of speech is first, and it’s the one you fight against first, and it’s the one that is unassailably important. As we are stress testing the Constitution and our government, I think it holds up very well, and it’s on us to make it stronger and to gird the foundations of it, but I am optimistic and it makes me love this country and being here because I do think at the end of the day, when you look at all these Americans and people and you show them what’s going on outside of an algorithm, outside of agitprop content, outside of all these things designed to break their brains, and you just get them all in the same place, like a picket line, a bar, a basketball game, and you go, “Isn’t this suck? Don’t you want something better?”

They’ll go, “Yeah.” And you go, “Okay, we can go do it.” And so I do think that’s the direction we’re headed. Not that we’ll all agree on everything, but that everyone can agree, or at least two-thirds of us can agree that this is bad and we want to do something different. So I do have hope in that.

Josh Gondelman: That’s wonderful. Thank you so much to all three of our panelists, Greg Iwinski, Sasha Stewart, Liz Hynes for talking to me about late night and free speech on writing podcast. This was really a wonderful conversation. I appreciate your time and your thoughtfulness. So thank you all so much.

Sasha Stewart: Thank you, Josh.

Greg Iwinski: Thank you.

Liz Hynes: Thanks, Josh.

Greg Iwinski: OnWriting is a production of the Writers Guild of America East. The series is produced by WGA East staff members, Jason Gordon, Tiana Timmerberg, and Molly Beer. Production editing and mix by Julia Yort. Original music by Taylor Bradshaw. Artwork is designed by Molly Beer. To learn more about the Writers Guild of America East, visit us online at wgaeast.org or follow the guild on all social media platforms @WGAEast. If you enjoyed what you heard today, please subscribe to the podcast and give us a five star rating. Thanks for listening. Until next time, Write On.

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