Late Night's Last Laugh

31 Jul 2025 · 47 min · 24 chapters

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In short

The cancellation of Stephen Colbert’s CBS late-night show (announced after Paramount’s $16 million settlement with Trump) becomes a lens on late night’s decline, its cultural role, and what political comedy can still do in a fragmented, clip-driven media era.

Guests (hosts of Critics at Large)

Vinson Cunningham (New Yorker writer), Alex Schwartz (New Yorker staff), Nomi Fry (New Yorker staff). Backgrounds discussed: Cunningham and Schwartz describe long personal fandom/interest in late night; Fry focuses on Colbert’s career and comedic/political evolution.

Key claims

Late night once offered a shared “monoculture” and a collective adulthood fantasy; fragmentation after the early 1990s and today’s podcast/clip ecosystem reduced that. Post-9/11 political satire (Jon Stewart, Colbert) “punctured” culture more directly than Carson/Leno. Colbert’s mainstream success depended on having a clear target (especially Trump). Trust between host and audience is central; if late night disappears, a training pipeline for writers and a cultural entry point for younger viewers may be lost.

Notable examples

Johnny Carson vs Letterman/Leno; Daily Show/Colbert Report; Colbert’s “Truthiness” segment; Strangers with Candy (Colbert as Mr. Knoblet); Conan’s “Team Coco” era; Taylor Tomlinson’s After Midnight monologue about “news now.”

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Stephen Colbert and Late Night's Future

0:45 to 3:41

Discussion of Stephen Colbert's career and the state of late night television.

“You know who also does, has been doing for many years, day in, day out?”

Historical Perspectives on Late Night TV

3:41 to 7:00

Hosts share their personal histories and perspectives on late night television's significance.

“So, you guys, this is not the first time we're talking on this show about media institutions in decline.”

The Changing Role of Late Night Hosts

7:00 to 10:10

Analysis of how the role of late night hosts has evolved since Johnny Carson's era.

“Something's unspoken, nudge, nudge, wink, wink.”

Political Comedy's Rise

10:10 to 14:00

Exploration of how late night television became a platform for political satire post-9/11.

“Robin Williams is making a joke about basically, you know, kind of paying homage to Johnny Carson and also treating him a little bit like a televangelist.”

Jon Stewart's Impact on Late Night Comedy

14:00 to 15:00

Explore how Jon Stewart transformed late-night comedy through political engagement.

“But when Stewart took over The Daily Show and I think is motivated by the sudden sort of hyper reality of the moment, the wars are going on, Iraq, Afghanistan.”

Comparing Late Night Hosts: Styles and Genres

15:00 to 16:00

Understand the differences in styles and genres between iconic late-night hosts.

“Let's talk about the great fear of the moment, whereas Johnny was kind of skating over the fear of the moment.”

The Evolution of Late Night Television

16:00 to 17:00

Discuss how the landscape of late-night TV changed post-9/11 and the rise of Jon Stewart.

“He's the David Foster Wallace of late night TV.”

The Leno vs Conan Controversy

17:00 to 18:00

Delve into the Leno-Conan debacle and its cultural implications in late-night TV.

“We were on the beach and the stupid just came in like a wave.”

Audience Identification with Late Night Hosts

18:00 to 19:20

Learn how audience identification plays a crucial role in late-night television success.

“And the network reneges and says, okay, whoops, like we're actually going to put Leno back in.”

Stephen Colbert: A Career Overview

19:20 to 20:20

Get an overview of Stephen Colbert's career and his evolution in comedy.

“You feel like he's your guy, he's your guy, and you're going all the way.”
Show all 24 chapters

Colbert's Unique Style: From Comedy Central to CBS

20:20 to 22:40

Explore Colbert's unique comedic style and its impact on late night culture.

“You can play catalogs every day at newyorker.com slash games and in the New Yorker app for iOS or Android.”

The Concept of Truthiness in Colbert's Comedy

22:40 to 24:00

Discover how Colbert introduced 'truthiness' and critiqued media through humor.

“And I've been pretty tough on you at times.”

The Influence of Cable News on Late Night

24:00 to 25:00

Analyze how the rise of cable news shaped late-night television hosts' performances.

“You think about Colbert comes up from Strangers with Candy.”

Colbert's Transition to Mainstream Late Night

25:00 to 28:00

Examine Colbert's transition from satire to mainstream late-night hosting.

“The thing I want to say about Colbert from the Colbert Report era is that he was a critic in a lot of ways.”

Transition to Mainstream: Colbert's Shift

28:00 to 28:35

Explore Stephen Colbert's transition from satire to mainstream late-night host.

“Yeah, so that's like, that's what makes it interesting to me that Colbert then went to this mainstream.”

Finding Footing Amidst Trump

28:35 to 29:40

Discuss how Donald Trump's rise influenced Colbert's late-night performance.

“Well, first of all, that motion is still a reflection that even as late as 2014, you know, the now halcyon late Obama era or whatever.”

The Role of Interviews in Late Night

29:40 to 30:29

Analyze the significance of celebrity interviews on late-night shows.

“I mean, I think this is a not totally unique to Colbert, but he became the grounding upon which the sort of urgent underpinning of this show could kind of rest.”

Colbert's Emotional Depth and Personal Stories

30:29 to 32:26

Examine how Colbert uses personal narratives and emotional topics in his comedy.

“And, you know, these are major, major promotion vehicles.”

Colbert's Philosophical Approach to Comedy

32:26 to 33:22

Listen to Colbert's insightful thoughts on faith and comedy.

“When he was a kid, his father and his two brothers died in a plane crash.”

The Complexity of American Identity in Comedy

33:22 to 35:33

Discuss how Colbert navigates themes of shame and pride in America through humor.

“There are other clips of him like trading lines of Shakespeare with Denzel Washington.”

The Future of Late Night Comedy

35:33 to 35:51

Speculate on the future relevance of late-night shows and their political impact.

“In a minute, Colbert's Late Show might be the first major network late night show to bite the dust.”

Colbert's Cancellation and Audience Trust

36:42 to 42:01

Explore Colbert's cancellation announcement and its implications for trust in media.

“We've been talking about Stephen Colbert and kind of trying to lay out the beats of his career and the way he's developed as a performer and a late-night host.”

The Relevance of Late Night Comedy

42:01 to 45:52

Explore the ongoing discussions about the future and relevance of late night comedy shows.

“Like, did they exacerbate an already very divided political landscape?”

Challenges Facing Modern Comedy

45:53 to 47:26

Understand the challenges comedians face in addressing current events and societal issues.

“And if you are having fun with it, something may very well be wrong.”
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Transcript

Automatic transcript. May contain errors.

0:05Alexandra Schwartz:This is Critics at Large, a podcast from The New Yorker. I'm Vinson Cunningham.

0:10Naomi Fry:I'm Alex Schwartz. And I'm Nomi Fry. Each week on this show, we make sense of what's happening in the culture right now and how we got here. Hi, everyone. Hello. How's everyone feeling? You know, we just got to keep on keeping on.

0:23Alexandra Schwartz:There you go.

0:24Vinson Cunningham:One foot in front of the other. That's what I tell myself on this Monday morning. That's what I tell myself every day and every minute.

0:31Alexandra Schwartz:The Midsummer slog.

0:32Vinson Cunningham:I've been in the middle of one deadline, one rolling deadline for the last, I would say, six weeks. I could not tell you what day it is. It's a miracle I know what month it is. Yeah.

0:41Alexandra Schwartz:Yeah. That's the life.

0:43Naomi Fry:That's the life. Well, Alex, you're talking about day in, day out. You know who also does, has been doing for many years, day in, day out? Mr. Stephen Colbert. Ah, yes.

0:56Alexandra Schwartz:Oh, yeah.

0:56Naomi Fry:Yeah. When did you guys become aware of Stephen Colbert? What was your first encounter with the man?

1:02Alexandra Schwartz:I think the sort of simultaneous moment during which he was on the Amy Sedaris vehicle, Strangers with Candy. And also, because I learned that he did this at the same time. And I guess this makes sense because he kind of like sprung into my life.

1:15Naomi Fry:This is the late 90s, right?

1:16Alexandra Schwartz:Yeah. He was also first a correspondent and then sort of a more and more prominent presence on The Daily Show with Killborn and then with Jon Stewart.

1:23Naomi Fry:Alex, what about you?

1:24Vinson Cunningham:For me, it was a little later than that. Probably in that 2003-2004 zone when the internet and watching things on it were increasingly a part of life, especially for a high school student who was outraged about the war in Iraq and the general idiotic politics of the United States of America at the time. Suddenly, there was this vehicle, The Daily Show, that expressed that in this really funny and youthful way. And there was this one particular guy on it who just embodied as a joke everything that we thought was going wrong. And that was Stephen Colbert. And it was huge. Right. Absolutely.

1:59Naomi Fry:So Stephen Colbert, currently the host of The Late Show, CBS's late night talk show, has been on our minds lately. Two weeks ago, he announced on air that Paramount, CBS's parent company, was canceling The Late Show. And this was only a few days after he called Paramount's settlement with the Trump administration, quote, a big fat bribe. about. Paramount is claiming that the cancellation is a financial decision. The show was apparently losing about$40 million a year, which I have to say sounds like a lot. But it does say something about the state of late night, the fact that, you know, the show is canceled, whether the decision really was economic or political or both.

2:41Naomi Fry:So today we're going to be talking about the late night show as a genre and also about Stephen Colbert more particularly as a political comedian and a satirist, and we're going to look back at what Late Night was doing for audiences before everyone's media consumption became so siloed. We're also going to look back to Colbert's work on The Daily Show, The Colbert Report, and even my favorite, Strangers with Candy. Shout out Mr. Knoblet. Late Night is an old form that, yes, has been losing viewers, but it still endures for now. Colbert himself will be fine. But is this cancellation a one-off, or is this the first late-night cancellation of many yet to come?

3:26Naomi Fry:So the question I have for us today is, what does Late Night offer us now? That's today on Critics at Large, Late Night's Last Laugh.

3:41Naomi Fry:So, you guys, this is not the first time we're talking on this show about media institutions in decline.

3:50Naomi Fry:or in potential decline, at least, to be kinder. We've talked about Saturday Night Live. You know, it's the 50th anniversary. Or we talked about Sesame Street not long ago and the changes that it has undergone over the last several decades. And this cold barren news feels like it might be another instance of a similar story, though potentially maybe with an even darker edge to it. I want to start off just by asking you guys, What's your relationship historically to late night television? Are you a fan? Like, is this something that has touched your life?

4:25Alexandra Schwartz:I feel that my relationship to late night television is very similar to my relationship to Saturday Night Live, which is that at a certain point in my life, I was very intensely interested in it. And I have retained a certain fondness and always kind of check in with it. It kind of retains a certain glamour for me. I think, I don't know, being the host of a late night television show. Like it's a man in a suit.

4:49Naomi Fry:It's a man in a sharp suit behind a desk. Behind a glossy desk. Talking to a famous person.

4:54Alexandra Schwartz:Yeah. And I have always loved the mix of sort of old school put togetherness, a man in a suit. But then also the variety of it. Okay, there's a band over there. Sure. There are going to be some sketches. There might be some man in the street. A celebrity is going to come by. This idea.

5:09Naomi Fry:There might be an iguana that'll like try to bite the host. Right.

5:13Alexandra Schwartz:Or an insult dog named Triumph. All kinds of different things are happening. There's a studio audience there. And it kind of is one of the building blocks to me of what I would call American entertainment.

5:26Naomi Fry:Oh, totally.

5:27Alexandra Schwartz:It's like Looney Tunes and late night TV are kind of these pillars of what I think we mean in America when we talk about entertainment. So I actually have always taken it pretty seriously. And I've always wondered, what's up with these hosts and what's going on next? So I'm a fan. I'm a fan.

5:45Naomi Fry:Alex, what about you? I think I recall you saying that it's not necessarily your genre.

5:52Vinson Cunningham:Late night television is for me a vision of adulthood that I still have. Like I can still step into myself as maybe a six-year-old or a seven-year-old who kind of stumbles out of the bedroom and hears the laughs on the TV where your parents are watching. and you think that's what it will mean to be grown up, I too will watch television, first of all, when I want. Second of all, late at night when I will be awake. There's a sophistication. What's going on on the screen at the midnight hour? And I retain that particular vision of late night because as someone, once I was able to stay up late, that's not really what I did with my late nights.

6:35Vinson Cunningham:I did not tune in. And yet I do identify it as this key part of the adult American media landscape.

6:43Naomi Fry:Yeah, I think that's so true, Alex. Like you're linking of the late night genre to a vision of adulthood. There is something about the interaction on late night when it's good, when it's interesting, that retains the slight frisson of like sex, danger, something unexpected. The wink that something's unspoken. Something's unspoken, nudge, nudge, wink, wink. You know, something that as a child, as you said, Alex, you might sense but not totally understand. But when you are on the other side, you know, you will feel a part of, you know, a member of. Like, again, separating the men from the boys or the girls from the women, you know.

7:34Naomi Fry:Do you think the genre is still doing for culture what it used to do for culture? Yes.

7:40Alexandra Schwartz:Oh. Oh, okay.

7:40Naomi Fry:Oh.

7:41Vinson Cunningham:I absolutely don't. Sorry. Oh. I just wanted to get everybody's attention. Yeah, I was like, really? I was like, you know what? Yeah, I just felt like I wanted that on me for a second. That was a curveball. I know. Such is the kind you might expect on late night every Saturday. Nice. See, this is the adult unexpectedness. Exactly. And now you can get it at any hour of the day from a podcast, and that's the point entirely. No, it's not doing the same thing. My God, you'd have to be crazy to think it was. You'd have to be totally under a rock. Look, two words for you. Johnny Carson. followed by a colon and a single word monoculture.

8:16Vinson Cunningham:Ah, yes. You know, Johnny Carson, who was the host of The Tonight Show for 30 years, 1962 to 1992. Do you guys know what his audience high was?

8:28Alexandra Schwartz:How many tens of millions?

8:30Vinson Cunningham:It was 12 million people. Jesus, yeah. That's a lot of people who were tuning in to watch what would go on with Johnny Carson. That is a collective experience that has not been there since the 90s. Like, you know, I do think we have a declinist narrative about what our media culture is. And in many ways it's justified. But that decline started in 1992 when Carson went off the air and suddenly there was Letterman and there was Leno and there was a viewership that was fragmented. And then I think also, and this is like, I'm so curious what you guys think about this, just a kind of style of humor.

9:01Vinson Cunningham:Like, you know, Carson is fascinating to me because you can't really tell the story of American entertainment and leave him out. He's so definitional, not just to the form of late night, but to comedy. And I was going down, not exactly rabbit hole, but I was looking at some old Carson clips. It's fascinating, like the kind of straight man congeniality. I mean, straight man in the comedic sense, not the sexual sense. Although that too. Although that too, yeah. Sure. But like the kind of, you know, like I watched a great clip of him playing across from Robin Williams the first time that Robin Williams was on the show.

9:35Vinson Cunningham:Do you want to show us this clip? So this is 1981. Okay. And Robin Williams is on Mork and Mindy, and he's getting to be more and more well-known. And, like, he's—I mean, the phenomenon of this man cannot be replicated. Still a coke addict this period, I believe. Yes, and they talk about that on the show. Oh, okay. So Robin Williams is coming out, and he's kneeling to Johnny. Believe! Believe that comedy can heal you!

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10:01Alexandra Schwartz:Praise the power! Praise the Jesus! And Sears had assailed his furniture in cheek. Oh, my God. You watch those guys on Sunday?

10:08Vinson Cunningham:So they're riffing, they're ranting, they're going back and forth. Robin Williams is making a joke about basically, you know, kind of paying homage to Johnny Carson and also treating him a little bit like a televangelist. Like he will be saved by him and they go back and forth on this. What's interesting to me about this clip is that Carson is able to both like play along when he needs to. He can do persona. He can do voices. He can do that stuff. But he also is getting out of the way to let Robin Williams do his thing. And he is a showman in that he's showing other people like he's he's providing the platform for other people, which, of course, again, is a sword that can cut both ways.

10:42Naomi Fry:Yeah. But he himself is sort of a cipher. Right. Which is an interesting thing and not necessarily the role of the late night host later on.

10:53Vinson Cunningham:Totally. I mean, after him, you get Letterman. And Letterman, of course, was the like, you know, a little bit of a snarky, a little bit of an edge, the mentee of Carson. I mean, Vincent, were you watching like Letterman and Leno in that era?

11:04Alexandra Schwartz:I did watch my earliest late night experiences were the so-called late night wars when there was this overt competition between Letterman and Leno, basically over the fact that both of them wanted to succeed Johnny and Leno was chosen to do that. Letterman goes to CBS. There's a lot of sort of on air sniping, not only at each other, but at the executives that sort of are their corporate overlords in both cases. And it's interesting to see like these different archetypes, right? Johnny and Letterman were similar in that they kind of loved showbiz and also had a twinkle in the eye that said it's also bullshit, right?

11:44Alexandra Schwartz:Whereas Leno, the classic Leno thing is not really behind the desk. It's him up doing these like corny jokes, doing the monologue. But in all cases, though, it was this kind of – to answer your earlier question, Nomi, like what's different about it to me is today perhaps a base sincerity. People that are very grounded in the world and are concerned whether it's about politics or otherwise. These guys were more like – there was a kind of friendly nihilism. That's like isn't it fun to be kind of nothing?

12:14Vinson Cunningham:Yeah. Yeah. It's really interesting. I mean, I was reading an article that our colleague Emily Nussbaum wrote on Letterman when he retired in 2015. And she was taking us back to a time before my memory in the 80s. She was describing how fresh Letterman felt then. And she has this line that I thought was great where she says, his manner suggested that TV could puncture the culture rather than prop it up. And, of course, the prop it up is what Carson did. And then you get this puncturing, which to me is very much like a preface or presaging of all the media culture that follows.

12:51Naomi Fry:Yeah. Although possibly in a different way, right? I mean, what happens after the late night wars, right? We have, Alex, the period you were talking about, right, with the Daily Show, the Colbert Report, the Bush era version of late night. And we should say that The Daily Show and the Colbert Report after it are on cable rather than the network late night shows we've been talking about. I mean, it was suddenly overtly political in ways which we'd never experienced in American entertainment and American late night, I think. Right.

13:24Alexandra Schwartz:Well, yeah, I think that's right.

13:26Naomi Fry:If we talk about this moment in late night, the grandfather of it has to be Jon Stewart. Yes.

13:31Alexandra Schwartz:And to continue this image of puncturing, I would say that the timeline starts at 9-11, which was a great puncturing of a kind of nihilistic surface of American entertainment writ large, right? Suddenly, everybody's thrust back into history. And if you remember that moment, everything was about how do you start again? How do we tell jokes again? How do we watch baseball again? How do we do things, again, that seem justified by the relative kind of Pacific surface of our lives in a way that isn't disrespectful to, like, the absolute shredding of our worldview? And Craig Kilbourne had preceded him.

14:12Alexandra Schwartz:But when Stewart took over The Daily Show and I think is motivated by the sudden sort of hyper reality of the moment, the wars are going on, Iraq, Afghanistan. Bush is sort of this obvious symbol of a certain kind of decline morally and geopolitically. And he engages with it day by day. And I think there is a large group of the culture that takes real solace in that. People talked about getting their news from The Daily Show. And this is one of the classic purposes of comedy, I guess. having their confusion, their sort of disorientation within the world confirmed, but also kind of maybe salved by someone who is acknowledging the same realities.

14:57Alexandra Schwartz:Stewart was funny because he was making the subtext the text. Let's talk about the great fear of the moment, whereas Johnny was kind of skating over the fear of the moment.

15:06Vinson Cunningham:Oh, definitely. It's a completely different beast. Yeah, they're two different things. I mean, it's interesting to me that we are able to really kind of like seamlessly slide from Johnny Carson to Jon Stewart because they are working in two different modes in two different categories. And I think this is where the Colbert of it all maybe comes in because in Colbert, you have someone who starts in one mode, which is the explicitly satirical, who then crosses over afterwards into the much broader made-for-a-wide audience late-night category. I mean, while Jon Stewart came on the air and started doing The Daily Show, it's not like that just suddenly became late-night television.

15:42Vinson Cunningham:Late-night television very much continued. It was still going on. Absolutely. Letterman is still on the air. Conan, who is a key figure who straddles both sides.

15:50Naomi Fry:We can't forget Conan. Certainly not. My favorite. How would you characterize him, Vincent, and the kind of matrix that we put out between Leno and Letterman?

15:58Alexandra Schwartz:He's Gen X. He's Post. He's the David Foster Wallace of late night TV. So you were saying there is a genre distinction here, which I think is totally right.

16:09Vinson Cunningham:Yeah, I think there's a genre distinction. You know, in late night television, there is, of course, politics does enter into it because the hosts are commenting on the news of the day. It's not like they're completely oblivious. No, of course. But in the Johnny Carson mode, it's neutral. And in the Leno mode, it's neutral. I think maybe the self-conception for the late night host is as, to use that little chestnut, an equal opportunity offender. Like, OK, Democrats do something dumb. We're going after that. The Republicans do something dumb. We're going after that. And I think what was going on in the post 9-11 years is that I don't know if the youngs coming up today.

16:44Vinson Cunningham:I mean, we live in such a nihilistic, dark time. So, like, you can imagine it. But the kind of sudden inundation of stupidity was it was a tsunami of stupidity that suddenly came from what had not been assumed to be a society in decline. Let's just put it that way. It was a surprise. We were on the beach and the stupid just came in like a wave. So when you could take advantage of that, like a Jon Stewart and make hay of it, then, yeah, of course you could siphon off a piece of that audience that otherwise might have gone to a Letterman type guy. Suddenly, that stuff, the Letterman stuff, which had been super edgy to the Gen Xers in the 80s, whoa, that became very square.

17:23Vinson Cunningham:There is a reason why Jon Stewart was what I was watching and not the Letterman stuff. There is one other thing I wanted to say, which I find really interesting. The Leno versus Letterman stuff, really before my cultural lived experience. Conan, not at all before my lived experience. That was huge. Conan, who's promised Leno's slot, the coveted 1130 slot, is told that he's going to get to inherit that slot, that Leno agrees in five years Leno will retire for The Tonight Show. Doesn't go so well. What happens? For those of us who don't recall. The network, NBC, moves Leno to an earlier slot to open for Conan.

18:04Vinson Cunningham:Bad news. Leno's bombing. No one's liking it. Conan's not doing well. No one's doing well. And the network reneges and says, okay, whoops, like we're actually going to put Leno back in. And basically if you were watching or even just marginally aware, which is, let's be honest, the category I was in of what was going on at the time. It was, what is this, Les Mis? It was a storming the barricade situation. Team Coco. A Team Coco. It was, you know, my people will not be denied. Give us bread. Give us water. Give us cocoa. How can you do this to us? How can you take this man who symbolizes us, you know, and guillotine him?

18:40Vinson Cunningham:We will not stand for it. And what I find so interesting about this is the identification with a late night host. That this is our guy. He speaks to us and he speaks for us. He is not just an entertainer. He is our entertainer. And when you get rid of him, you get rid of us. And it's touching to me now to think of the digital world rising up in support of this old medium. But they did. And I think it has to do with a particular reality of late night when it works well. which is that it is an art form and it is an art form of identification to some degree. So that host needs to be the avatar for a bunch of viewers.

19:21Vinson Cunningham:You feel like he's your guy, he's your guy, and you're going all the way. And that is not an accident. That is a performance skill that the best late night hosts have.

19:35Naomi Fry:Stephen Colbert has been a fixture on the late night schedule for over two decades. In a minute, how his comedic stylings have evolved to meet the culture. This is Critics at Large from The New Yorker.

20:14Vinson Cunningham:Transcription by CastingWords by population, or Martin Scorsese movies by release date. You can play catalogs every day at newyorker.com slash games and in the New Yorker app for iOS or Android. Here's a helpful hint. The app gives you free access to our entire archive of catalogs, along with our word scramble

20:33Alexandra Schwartz:game Shuffalo and the mini crossword. So download the New Yorker app for new games to play every day.

20:46Naomi Fry:Okay, you guys. So we've been talking about late night. And what I want us to do now is to turn more particularly to the figure of Stephen Colbert to discuss what's been going on with him right now. But before we attack the current landscape and his role in it, can someone maybe give us a brief overview of his career and who is he? You know, kind of like greatest hits of Colbert. Who even is he? Who is he and how dare he? Well, you guys are the Strangers with Candy Watchers. I can start from that. Start. So, OK, for those of you unfamiliar and God, you really, really need to familiarize yourself if you're not.

21:29Naomi Fry:A Comedy Central show from the late 90s, Strangers with Candy, where Amy Sedaris plays Jerry Blank, a 46-year-old former kind of 70s runaway junkie who has gone straight and is returning to high school, to ninth grade. I'm just thinking about it. Makes me laugh. because she dropped out of high school when she became a teenage prostitute runaway in 1975. And there are two teachers, Mr. Knoblet, who is played by Stephen Colbert, and Mr. Jellinek, who's played by Paul Danilo, who were also involved in making the show and writing the show. And the whole thing hinges on the fact that the show is like an after-school special gone wrong.

22:22Naomi Fry:And the role of Colbert is to be this teacher who's supposed to teach Jerry all of these lessons, but is completely hateful and bitter and, like, despises her.

22:36Alexandra Schwartz:This has been a real roller coaster of a year. And I've been pretty tough on you at times. I'm sure you think that I hate you. But I want you to know that I hate you. I hate you too, Mr. Napoli.

22:53Vinson Cunningham:I guess we shouldn't hug. Yeah, probably not. Okay.

22:57Naomi Fry:Completely, actually, a very, like, weird, extreme, nihilistic show. Extremely funny. So that was the first time I encountered Stephen Colbert. So completely not in the mold in any way of a kind of, like, smooth, late-night host. but in fact is a kind of spiky, pretty alternative comedian.

23:20Alexandra Schwartz:I think that's really important what you just said.

23:22Naomi Fry:Oh, okay.

23:23Alexandra Schwartz:Because.

23:24Naomi Fry:I'm like, oh.

23:25Alexandra Schwartz:Much of what you say is important. He started out, he went to Northwestern, thinking he was going to be a dramatic actor, and got caught up, as people do when they go to Chicago, in the world of improv and sketch comedy.

23:37Naomi Fry:Yeah.

23:37Alexandra Schwartz:So he was in that world of improv and sketch of the Second City, the annoyance, et cetera. And if you look at the current crop of late night hosts, Seth Meyers, Jimmy Fallon, sketch performers, if the previous era's kind of archetypes were stand ups, which we think of as people who tour the entire country, sort of becoming weather vanes for public opinion and sort of reflecting that or the radio host who is kind of a genial cipher. even Conan was a was a sketch sort of TV writer with the sort of famously wrote the

24:17Naomi Fry:the monorail episode of The Simpsons one of the best episodes ever but if you think of the

24:22Alexandra Schwartz:sketch performer as an archetype all of a sudden it's not somebody who you'd find in Las Vegas which is to me it seems to be the corollary of the late night sort of hosts vibe all of it It's somebody who grows up in community and urban enclaves with a certain political orientation. You think about Colbert comes up from Strangers with Candy. He's a very pointedly satirical performer on The Daily Show. Bringing his biography along with him, he comes from a Catholic family. He's a practicing Catholic. He used to do this bit on The Daily Show called This Week in God, giving these pointed spins on the evangelical culture in America that was kind of rising at the time.

25:03Alexandra Schwartz:And then he starts to don this character, Stephen Colbert of The Colbert Report, who is this faux-intelligent ignoramus whose bigotry is part of the deal and found this really smart way on his own show, again, before he sort of joins the real late-night game on CBS, to sort of speak through a character that shows his contempt for the current culture, but also make kind of sincere volleys of connection with his guests.

25:37Naomi Fry:It's a weird type of performance art. It was kind of amazing. It's kind of crazy to think about.

25:41Alexandra Schwartz:It was more than kind of amazing.

25:42Vinson Cunningham:It was amazing. Yeah.

25:44Alexandra Schwartz:Yeah.

25:44Naomi Fry:Do we want to talk about truthiness?

25:46Vinson Cunningham:Yes. The thing I want to say about Colbert from the Colbert Report era is that he was a critic in a lot of ways. And that was a very interesting form to take on in this otherwise totally comedic performance. So Truthiness, right, as you've said, Nomi, he introduced a segment called The Word.

26:05Naomi Fry:The first episode of the show, I believe. Well, there you have it.

26:08Vinson Cunningham:Just brand spanking new. Yeah. Shall we listen in?

26:13Naomi Fry:Let us listen into the clip.

26:17Vinson Cunningham:Truthiness. Now, I'm sure some of the word police, the wordinistas over at Webster's, are going to say, hey, that's not a word. Well, anybody who knows me know that I'm no fan of dictionaries or reference books. They're elitist. The truthiness is anyone can read the news to you. I promise to feel the news at you.

26:44Naomi Fry:Okay, this strikes me as, like, insanely prescient.

26:49Vinson Cunningham:Yeah, I think it, on the one hand it is, and on the other hand I do think there's a bit of a, Because, again, times are so bad, I think there is a bit of a forgetting about how bad they felt then, too. Like, that was also the reality then. It's both prescient, but it's also just it is what was happening. I was just I'm not trying to quibble with the fact that it's prescient. It is. I just would put a slightly different spin on it, which is to say that it was diagnosing an ill in the culture that has become more and more extreme. Oh, absolutely. And it got it and it diagnosed it and it gave an emotional outlet to viewers.

27:21Alexandra Schwartz:And, you know, the other thing about that, the other thing that that performance reflects, he's a critic not only of politics but of media, which is that he's responding to the rise of cable news and that kind of host.

27:35Naomi Fry:Absolutely.

27:36Alexandra Schwartz:So you're thinking about Bill O 'Reilly, thinking about Sean Hannity. Later on in the 2000s, in the aughts, I guess, we get Rachel Maddow, etc. That kind of performance, which is, again, this kind of amazingly direct address and a kind of startling, demented sincerity, makes its way via Stephen Colbert and this performance into what it means to be a late night host.

28:03Vinson Cunningham:Yeah, so that's like, that's what makes it interesting to me that Colbert then went to this mainstream. Right. Like then he decided to, in 2015, to jump into the mainstream. Right.

28:12Naomi Fry:He is this figure suddenly of the kind of mainstream conventional, you know, late night host. He is Carson. He is Leno. He is Letterman. He is that guy. So what happened then? Like, how does one transition from playing the satirical character to becoming like America's father suddenly, you know?

28:36Alexandra Schwartz:Well, first of all, that motion is still a reflection that even as late as 2014, you know, the now halcyon late Obama era or whatever. Relatively halcyon, I guess. Yes. It still was like the only way to get bigger as an entertainer is to take on a late night show. We would have been like, what? Stephen Colbert is starting a podcast? Is he broke? You know, there was still this ideal of upward motion in the Hollywood firmament. Totally. But if you look at the early reviews, one of which was from our much beloved colleague, Emily Nussbaum, friend of the pod, the first year or so was not so good for that Colbert show, because I think, again, as a performer, his gift was a kind of critical or responsive orientation toward culture, not just kind of sitting atop it and having fun with it.

29:31Alexandra Schwartz:So it takes him until the rise of Donald Trump to really find his footing behind that desk because he had a target. And so Trump become as he became for Kimmel and Myers and others. I mean, I think this is a not totally unique to Colbert, but he became the grounding upon which the sort of urgent underpinning of this show could kind of rest.

29:56Naomi Fry:Everybody got the Trump bump, you know, whether it was conventional media, whether it was The Times, the, you know, the kind of news media and whether it was, as you say, late night at large, like suddenly there was something. I mean, as the country was going down the toilet, there was something to, yeah, as you say, to respond to.

30:16Vinson Cunningham:Yeah. Yeah. It's interesting to me, Nomi, that I was not watching Colbert in this era. I was not watching the late show. I just didn't care about him sitting around talking to celebrities. I mean, that's a whole other aspect that we haven't even gotten into yet, really, of what it means to have a late show. It's interviews. It's conversations. And, you know, these are major, major promotion vehicles. Less than they were, but certainly they endure. Absolutely. And I would actually argue that the desperation is higher. But I do think that during that era, what tended to break through into the digital culture that I was part of, that I remain.

30:54Vinson Cunningham:You're a bit of a digital native, Alex. I'm a bit of a digital native. It's just what happens when you're, you know, born at a certain time in history. And, you know, that was the time when Carpool Karaoke, the James Corden bit, would kind of – that would leak through.

31:10Alexandra Schwartz:A literal vehicle.

31:11Vinson Cunningham:A literal vehicle. A literal vehicle. Yes.

31:13Alexandra Schwartz:Oh, my God.

31:13Naomi Fry:What a nightmare. Like, what a – Tell us how you really feel, though.

31:18Alexandra Schwartz:You don't want to hear James Corden harmonize with – No.

31:22Naomi Fry:Paul McCartney?

31:23Vinson Cunningham:No, absolutely. There was a sweet one where they did that. I mean, it's sweet, I guess, but it's like, this isn't, it's certainly not comedy.

31:32Naomi Fry:It might be entertainment, but even that is like the blandness and conventionality of the format has become such that really, Alex, I agree with you saying, yeah, I wasn't interested in really watching.

31:50Vinson Cunningham:Well, if Colbert had a version of that and, you know, let us know in the comments, it's news to me because I don't think that's what he was doing.

32:00Alexandra Schwartz:Yeah. And I will say, sticking up for Colbert, this what you mentioned before about sort of identifying. I kind of feel I kind of a little bit feel like that about Colbert. I kind of he's my favorite, I think. And I will say definitely he was the best conversationalist. Can I play something for you guys? Yes. Real quick. What he did was he could really go into things. He would talk about his faith. He would talk about grief a lot. I don't know if he has a very Joe Biden-esque story. When he was a kid, his father and his two brothers died in a plane crash. He could really talk in a kind of emotional and direct way to people.

32:35Alexandra Schwartz:But here is actually Dua Lipa asking him a question. And it's a great moment, I thought.

32:41Vinson Cunningham:I was wondering, does your faith and your comedy ever overlap? I'm a Christian and a Catholic, and that's always connected to the idea of love and sacrifice being somehow related. In the same way, that sadness is like a little bit of an emotional death, but not a defeat if you can find a way to laugh about it. Because that laughter keeps you from having fear of it. And fear is the thing that keeps you from turning to evil devices to save you from the sadness. As Robert Hayden said, we must not be frightened or cajoled into accepting evil as our deliverance from evil. We must keep struggling to maintain our humanity, though monsters of abstraction threaten and police us.

33:22Vinson Cunningham:Oh, my God.

33:23Alexandra Schwartz:And he was like that. There are other clips of him like trading lines of Shakespeare with Denzel Washington. It's not Johnny Carson just letting Robin Williams do the thing. and that kind of philosophical underpinning I do think connects to the way he also then dealt with politics. It came from a very sincere bedrock so that even when he was being his most silly and abstract, which he could get, there was some link there that has kind of almost nothing to do with Johnny Carson. Do you know what I mean?

33:59Vinson Cunningham:You know, I'm so glad you showed us that clip And now I wish I had been watching more in the years when I wasn't. And I wasn't not watching because I thought it was dumb or something. I just was, you know, in my own media landscape looked different. And, you know, I'm sorry. But just now hearing Stephen Colbert or Colbert, as he reminds us he's Irish, as it used to be before for media purposes, it was funnier to say Colbert, quote, poet Robert Hayden. I mean. Your eyes filled with tears, Alex. In part because I felt also that he was defending the dignity of America. You know, we are laughed at as idiots by the rest of the world, and often we deserve it.

34:38Vinson Cunningham:It's just true, you know? But look, here is an entertainer going on his very popular top-rated late-night show and, like, giving wisdom when he's asked for it. Okay, I'll take that. I will stand a little bit taller. And I think that's what also, to go back to the earlier Colbert Rapport persona, that was part of it. It had so much to do, as an American, it had so much to do with, did you feel shame or did you feel pride? Those were like the two poles of experience. And the complexity, the reality of what it means to be any kind of person, let alone an American person, you know, often got crowded out.

35:17Vinson Cunningham:And Colbert was such an effective way to take the shame and make it into some kind of pride. You know, yes, we're in the shit, but at least we have an intelligent and funny way to analyze it. And this is a different version of that to me. But I'm glad to have discovered it. Yeah.

35:35Naomi Fry:In a minute, Colbert's Late Show might be the first major network late night show to bite the dust. But let's be honest, it probably won't be the last. Where do late night and political comedy in general go from here? This is Critics at Large from The New Yorker. Stick around.

36:21Naomi Fry:that we're looking at.

36:22Vinson Cunningham:Join me, Evan Osnos, and my colleagues Jane Mayer and Susan Glasser every Friday on The Political Scene, available wherever you get your podcasts.

36:41Okay.

36:42Naomi Fry:We've been talking about Stephen Colbert and kind of trying to lay out the beats of his career and the way he's developed as a performer and a late-night host. And now we are coming to the moment that we began with, which is Colbert, you know, being canceled, announcing this cancellation on air a mere three days, I believe, after basically saying that Paramount paid off President Trump.

37:09Vinson Cunningham:Paramount paid Donald Trump a 16 million dollar settlement for a nuisance lawsuit Trump filed claiming that 60 Minutes deceptively edited their interview with then candidate Kamala Harris last fall. Paramount knows they could have easily fought it because, in their own words, the lawsuit was completely without merit. Now, I believe this kind of complicated financial settlement with a sitting government official has a technical name in legal circles. It's Big Fat Bribe because—

37:36Naomi Fry:And this, it has been alleged, was in the service of Trump not blocking Paramount's merger with Skydance. Which did then go through. Which did then go through. And so the whole thing smells not great.

37:51Alexandra Schwartz:Smells to high heaven.

37:52Naomi Fry:It smells to high heaven, my friends. So it's kind of unprecedented, I guess.

37:59Vinson Cunningham:Yeah. Certainly the bribe is the first instance I can think of where$16 million has been paid to a sitting president by a media company because that president got pissy.

38:12Naomi Fry:Yeah.

38:13Vinson Cunningham:I would call that unprecedented. Yes.

38:15Naomi Fry:So, Vincent, after the cancellation was announced, after Colbert himself announced the cancellation on air, you wrote a piece.

38:23Alexandra Schwartz:Yeah. Well, what I cared most about was the lasting, I think, strand of communication between host and audience that Colbert's announcement sort of laid bare. As it was reported, first of all, the show's being canceled in May. So next May.

38:44Naomi Fry:Which he said, right?

38:45Alexandra Schwartz:Yeah. And they didn't want to announce the cancellation right now, but he said, nope, I'm going to announce it. And so there was still a bit of that thrill, certainly an attenuated version of it. But it was there that this person could tell you some version of the truth. And that's what I was interested in when you talk about a figure in the entertainment firmament being something like a critic. Even to say that is to confirm a kind of shared reality, but more importantly, shared method of interpretation. And so if there are fewer, and I don't mean this as a defense of monoculture or whatever, but if there are fewer things on which we can agree, fewer voices that we think are kind of even genially uncorrupted by, you know, whatever, the Carson thing of like acknowledging, not acknowledging, irony, whatever.

39:36Alexandra Schwartz:To me, that confirms the sense that there's no ground to stand on.

39:40Vinson Cunningham:So I think you're getting at something that has to do with trust and trust in a certain kind of voice. And trust, look, it's so misplaced in so many people right now. You know, looking to all the wrong people for the answers, whether they be in politics or in media. So what your piece made me think about was how someone like Colbert or any other late night host is working with this idea of trust. You know, he has to have the trust of the audience in order to be able to do his job. And in some ways, like, now that he's in this position where he can just say what he wants and what can happen. He's going to be fired.

40:20Vinson Cunningham:He's already been fired. Like, he can just tell us what he thinks. That trust, I don't think it went away. But, like, now he really has it, you know, for some of his viewers at least. Don't you think?

40:32Alexandra Schwartz:I would say so, yeah.

40:33Vinson Cunningham:So that might make for a very interesting few months.

40:38Naomi Fry:But I want to ask you, Alex and Vincent, you know, this question of trust, obviously, as you implied, Alex, happens in the context of like half the country trusts. You know, there are many more divisions than half and half. But let's say, you know, half the country trusts one side and despises the other side and the other half the opposite. And we, because we are liberals, would like Colbert to, you know, like nothing to lose, going to speak truth to power. But there is a question and it has been argued, I think, that the kind of political humor that was championed by people like Colbert or Jon Stewart contributed to that siloing and enacted a kind of like liberal smugness that made the other side, quote unquote, dig their heels in.

41:34Naomi Fry:What do you think of that argument? That humor rather than kind of like somehow ameliorating or it is actually something that is hastening the siloing.

41:46Vinson Cunningham:Yeah. I mean, who cares, honestly? Like, oh, my God. You know, oh, oh, yes. Jon Stewart is the problem. You know, get that man. Like, I don't mean to be so sarcastic about it for sure. You know, you can talk about it. But but here's ultimately like the power is not with the comedians, I think, is is what I mean to say, sadly. Like, did they exacerbate an already very divided political landscape? Maybe, but I don't think by all that much. Like, I don't think having like a more kumbayage take, like, let's all gather around the burning flames of the United States and like warm ourselves by them would be any better.

42:22Naomi Fry:Which brings us to a kind of the larger question, right, which I think we've been working towards throughout this episode, is that is late night even a relevant art form anymore? I mean, Colbert is the first to be canceled and there's the whole Trump thing. But maybe in general, this is not something that is like long for this world. Yeah. And a lot of the hosts, the main host contracts are up in the next couple of years. Kimmel's contract is up in 2026. I believe Seth Meyers and Fallon is up in 2028. And so, you know, we might be approaching a moment where potentially post late night, maybe. Who knows?

43:05Vinson Cunningham:Yeah, I think that's quite likely. I mean, as with many of the older media, ha ha, I say looking at the two of you. I guess the bigger question then is what is lost or gained with that. One thing I'd imagine would be lost with the demise of Late Night is the same thing that's lost if magazines go totally belly up, which is a pipeline for younger people to create, to learn, to get their sea legs, to get a voice. I mean, these writers' rooms and the technical aspects of the job are stocked. It's not just the guy in front. You know, it's all the people coming up through that. And inevitably, that's a big loss if those ways of learning and doing go away.

43:47Naomi Fry:But it's also the viewers, right? The many, many, you know, relatively young people who used to learn about the world and ways of interacting with entertainment and politics through late night shows.

43:58Vinson Cunningham:Well, that's already gone. I mean, that's already going. It's this comes back to your piece, Vincent, like this idea that Colbert is the mouthpiece who can kind of articulate from what's going on from the halls of power directly to the audience. The problem posed by something as extreme as the Trump era is that if your job like late night hosting is an art, but it's also business. And so if your job is to get as many eyeballs on you as is humanly possible, what do you do? And it makes me think of something I saw recently, which is the comedian Taylor Tomlinson, who did a show called After Midnight.

44:35Vinson Cunningham:And it was also CBS. And this show, I remember it being discussed, like the run-up to it was, okay, first of all, a woman is hosting late night. Yes, it's at 1230 a.m., but people will watch it the next day. People will watch it in clips. That's the whole point. It basically becomes what you watch with your breakfast. any young woman. She is now in her early 30s. It's a very different kind of face. And the show has ended. So did it work? Like, perhaps not. I think there was some talk that she was asked to renew it. She didn't want to, whatever. But I wanted to play for you one of her last opening monologues, which happened a few weeks ago after the protests against ICE arrests in Los Angeles.

45:13Vinson Cunningham:And here she articulates from the point of view of a late night host what the problem is with trying to mine reality for the job. We have a lot to discuss about what happened in L.A. this weekend. And most of it is not funny, but late night shows aren't funny anymore anyway. We're just the news now. This is the last week of the show, so I'm just going to say, one of the hardest things about doing this show is a note we kept getting was like, what's on Taylor's for you, Paige? What's Taylor watching? And I'm like, what's on Taylor's for you, Paige? Ice raids, genocide in Gaza, Trump, that's what's on Taylor's for you, Paige.

45:49Vinson Cunningham:It's not a good time. So she's articulating exactly what we're talking about, which is it's not easy to have fun with the news as it is. And if you are having fun with it, something may very well be wrong.

46:01Alexandra Schwartz:And I do think that this problem, what to do to be the liberal scold, to be the sort of Mr. Political or to go or be the kind of anti-woke equal opportunity offender, which I think is a thing that has worn thin or to go personal and sort of like telescope and leave the political outside of your purview. It just seems that all of the options for comedy right now are unsatisfying. And I love comedy. I love stand up. I love Late Night. I love all of these forms. I love Sketch. But they all seem to be turning their wheels, going nowhere, precisely because of the problem that Tomlinson articulates.

46:42Alexandra Schwartz:It's hard to – I mean, I feel this in my writing. It's like, you know, why am I writing about Stephen Colbert even?

46:47Vinson Cunningham:Yeah, it may be that one reason for that – I think you're absolutely right. And I think one reason for that is what comedy can do really well is kind of excavate hypocrisies and the stuff underneath the surface. This is why the Bush era was kind of perfect for it, because the Bush era pretended to be normal. It pretended to be like normal politicians doing normal things. And what was going on was torture, warmongering, like dismantling of American education, just great catastrophes. But they were maintaining a facade. Yeah. There is no facade right now.

47:19Alexandra Schwartz:It's mask off. And comedy exists often to sort of be the first responder to the problems in the culture. So one of the promises, scant but still of the moment, with Colbert at least, is to say, okay, show us something new. Now you've got this freedom, right? And maybe you're in a position to do something else with the medium that shows us what could possibly be on the horizon.

47:55Naomi Fry:This has been Critics at Large. This week's episode was produced by Michelle O 'Brien. Alex Barish is our consulting editor. Our executive producer is Stephen Valentino. Condon S head of Global Audio is Chris Bannon. Alexis Quadrado composed our theme music. And we had engineering help today from James Yost with mixing by Mike Kutchman. You can find every episode of Critics at Large at newyorker.com slash critics.

48:33Vinson Cunningham:Is Wuthering Heights really a love story? Should you be afraid of Virginia Woolf? And most importantly, is Mr Darcy handsome enough to tempt you? This is The Secret Life of Books. I'm Sophie Gee, academic and writer. And I'm Jonty Claypole, broadcaster and producer. In this podcast, we tell the story behind the story of the literary classics everybody wants to read, feels they should read, or has already read and loved. We reveal their secret histories, hidden players and big ideas behind the great books. We show how they came into being, why they matter and how they changed the world. The deeper we go, the weirder the questions.

49:09Vinson Cunningham:Is George Orwell's 1984 on some level a comedy? Is Dracula the Freddie Mercury of horror? And why do so many literary honeymoons go wrong? Whether you're a committed book nerd or just curious about the history of ideas, The Secret Life of Books is the podcast for you.

From the publisher

Two weeks ago, when Paramount cancelled “The Late Show with Stephen Colbert,” insiders in Hollywood and Washington alike deemed the move suspicious: Colbert had just called his parent company’s payout to Trump a “big fat bribe” on air. Paramount, for its part, claims that the decision was purely financial—Colbert’s show is losing forty million dollars a year. But both the political and economic explanations reveal how the landscape of late night has changed since Johnny Carson’s day. On this episode of Critics at Large, Vinson Cunningham, Naomi Fry, and Alexandra Schwartz consider Colbert’s body of work and the state of the genre more generally, from the so-called late-night wars of the nineties through to the modern challenge of making comedy in a country where nothing feels funny anymore. “Late-night hosting is an art, but it’s also business. So, if your job is to get as many eyeballs on you as is humanly possible, what do you do?” Schwartz says. “It’s not easy to have fun with the news, as it is. And if you are having fun with it, something may very well be wrong.”

Read, watch, and listen with the critics:

“Strangers with Candy” (1999–2000)
“The Daily Show” (1996–)
“The Late Show with Stephen Colbert” (2015–26)
“The Staying Power of the ‘S.N.L.’ Machine” (The New Yorker)
“Lessons from ‘Sesame Street’ ” (The New Yorker)
“The Tonight Show Starring Johnny Carson” (1962–92)
“David Letterman’s Revolutionary Comedy,” by Emily Nussbaum (The New Yorker)
“The Colbert Rapport,” by Emily Nussbaum (The New Yorker)
“Carpool Karaoke” (2017–23)
“What the Cancellation of Stephen Colbert’s ‘Late Show’ Means,” by Vinson Cunningham (The New Yorker)
“After Midnight” (2024–25)

New episodes drop every Thursday. Follow Critics at Large wherever you get your podcasts.

Critics at Large is a weekly discussion from The New Yorker that explores the latest trends in books, television, film, and more. Join us every Thursday as we make unexpected connections between classic texts and pop culture.

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