From left: Will Menaker, Virgil Texas, Felix Biederman, Brendan James, Matt Christman, and Amber A’Lee Frost onstage at Littlefield in Brooklyn, New York. (Photo: Brendan James)

Bestcasts asks podcasters to discuss the three most memorable episodes of their podcast. For more podcast coverage, see Podmass, The A.V. Club’s weekly roundup of the best ’casts out there.

The podcasters: Though the show was conceived between mere Twitter acquaintances and first recorded via joint Google Hangout just 16 months ago, the podcast Chapo Trap House—originally helmed by Will Menaker, Felix Biederman, and Matt Christman—has since become a snowballing force of Leftist ethos, swiftly cultivating an energized fan base of so-called Grey Wolves who are revitalized by the show’s unabashed callouts of neoliberals and arch-conservatives alike.


Now featuring three additional hosts (Amber A’Lee Frost, Virgil Texas, and Brendan James) and a recently announced book deal, Chapo Trap House has seen a meteoric rise that James attributes to “a chemistry born of internet chicanery.”

Episode 3: Freeway Ross Douthat Sailboat Dope


The A.V. Club: Why did you choose this episode?

Brendan James: To be honest, we chose this one because Ross Douthat was such an important and formative influence on our “gospel,” and that first reading series of [Douthat] being on a boat with William Buckley with all kinds of bizarre and creepy undertones was when we knew that we had found some magic in what was, up until then, kind of just a joke. He’s been a figure that we love to lampoon ever since, and that was where it all started. A lot of people say that’s their favorite reading series, the very first one.

Felix Biederman: It’s when we first established a rhythm with the “reading series” bit. The crux of the reading series is Will finding the absolute worst parts of whatever we’re reading, Matt using historical context to go off about something, Brendan’s [knowledge of the] publication history of whoever we’re making fun of, and me, going in and out, making fun of whatever they’re saying. When you brought all that together, we saw why that was so funny, and it’s why we use [reading series] so much.


BJ: In the first two episodes, the chemistry’s already there, but then the third episode is when it started to hit its stride. There’s definitely a sense of structure and form, where we’d start with news and then go into some articles, and then we do a reading series at the end. That became the basic way we still do the show.

AVC: By episode three, considering the technological limitations, and the fact that nobody was recording in the same place, the chemistry is already pretty remarkable. To what extent did people really know each other?

BJ: I don’t think most of us had met Matt until he came up that summer for our first live show. I had met Will; I don’t know if Felix and Will had met yet. We hadn’t even known each other on the internet for very long.


Matt Christman: I hadn’t met any of them yet.

Will Menaker: The first two episodes we were just recording in Google Hangouts. Laughably incompetent, completely flying by the seat of our pants. When we got Brendan on as a guest to talk about Sean Hannity, he just said, “I mess around with audio stuff as a hobby, if you need anyone to edit the show.” The rest is history. So that was the reason it was the most memorable one—that’s when I feel like it first came together as a competent podcast unit. We still had a ways to go before we got to our current status of shabbily semi-professional.

FB: We were lucky—we had been on other people’s shows before that. It allowed us to work through that awkward adolescence.


MC: We had had so much time bouncing off of each other on Twitter. If you do a lot of riffing, you get to understand people’s point of view and their comedic voice.

AVC: Do you think the “Chapo reading series” is the crown jewel of what you bring to podcasting?


MC: I really think so. Will was an editor at Liveright, and he doesn’t read the whole article [during our reading series]. He’s picking the best moments, so he’s already doing the editorial work of shaping it into something better than it would be if we just read the whole thing. So he’s leading us through it. He’s like the Virgil—not our Virgil, but Dante’s Virgil—leading us through the inferno of this awful conservative prose.

Me and Felix really come at it from different angles. He’s a born poster shitlord joke man—he has a fast-twitch-muscle joke response. And I try to tease out the pathology. What is actually happening here? When [Douthat’s] saying this, what is the weird, unspoken, Lovecraftian thing?

That [reading series] format really lends itself to what we do best. You can make points, do an annotation of what’s stupid and what’s wrong, and tease out the logic problems and misconceptions undergirding it. But also, you can get really personal and mean about the weird pathologies on display by the people writing it.


It’s hard to read Douthat—he’s incredibly lugubrious. So that was us finding it all at once. Get a weirdo conservative with a horrifying personal anecdote, and then just let them do a lot of the work. You just have to come in and pick your spot to have an observation or a joke. It’s like when Jed Clampett shot into the ground and the oil came up.

WM: It’s what the show became known for off the bat. It was a thing we did that nobody else was really doing. Someone actually said it as an insult—that we’re the Mystery Science Theater 3000 of politics. Well, yeah, that’s great! That’s exactly it. Three wise guys exposing ourselves to this mind-numbing drivel—in this case, op-eds and writing that we hate.

Every time we make fun of someone, they become a character. They keep coming back, because obviously they’re still working, they’re still around. So I like that we’re creating a universe, and I think that’s a lot of what attracts people to this show.


FB: Episode three is important in how listeners responded. It made Ross such a big part of our canon. Listeners understood immediately why he’s such a funny type of character. We don’t have passive listeners, and that became really clear.

Episode 58: We Live In The Zone Now


AVC: This was the first episode after the election.

WM: One of our most instantly popular. And that was a weird one, because we had an infamous live show on election night. It felt like we were watching the world end on stage. Halfway through the show, things just weren’t funny anymore. We just had to keep going.

BJ: It was actually the same episode when The New Yorker was in the room profiling us. Everyone was very raw, but our job was to make people laugh in that hour. So we switched to a mode that came across as upbeat, but it was not. We were all as creeped out, as threatened by what had happened, as loads of other people in the country were. It was very eerie and unreal to do that episode.


What Matt said on the night of the election was, “This show is over. We’re done.” He thought, not unjustifiably: How are we going to be funny or different if we have to deal with Trump? The New Yorker profile was sort of taking that question up—how are these guys going to do what they do with this new cartoonish and crueler and more high-stakes crisis in American politics?

MC: I was panicking. I genuinely thought it was over. We thought, if he wins, then we’ll just be listing Trump’s goof of the week. But this episode, and the response to it, is really what reassured me that that wasn’t going to happen.

FB: Our listeners know when someone is cynically trying to appeal to them in some way, or trying to match their emotions, or worse yet, guide their emotions. But when we present as we feel, they really respond to it. Oftentimes, we feel the same way that they do.


WM: We got a huge bump from that show, because we were all still raw and dazed, as many others were—and really pissed off. When we did that episode, we let it all out. The anger at being underserved really crystallized after the disaster of the election. We live in the zone now—there’s no going back.

AVC: Everyone was angry and upset in the wake of the election, but this episode allowed people to direct that anger back inward at the Democratic Party they felt had betrayed them.

MC: That’s the reason [this episode] sparked so much. It was the one thing that allowed you to get mad, not in the way that everyone else was telling you to get mad, and maybe get toward an anger that was productive—because it actually identified the problem, as opposed to being showy venting.


Within a month of the election, we were hearing about people joining the DSA [Democratic Socialists Of America] and talking about us as an inspiration for doing it. We weren’t saying “go join DSA.” We weren’t talking about it on the show. I think you just listen to that episode, and it doesn’t tell you that you’re “in good hands.” The Bush administration [era], The Daily Show’s Rally To Restore Sanity era, told you that there were institutions that had your back, that the Democratic Party and the media were bedrock institutions that would prevent the worst. You have this galloping fascism arising from the hinterlands in the form of the Tea Party, and the response to it being, “Well, let’s critique their aesthetic presentations.”

BJ: That was an episode with the widest scope of emotion and hope and fear and sentimentality and irony that you’re going to get in one episode. And it might as well be that one. It was as raw as any of us were ever going to be—yet. I have no idea what’s coming.

WM: That post-election episode was the horrible coda to the entire first half of the show. That was the day we said, okay, let’s bring in Virgil and bring in Amber [as co-hosts], and expand the show and see where it goes. That was another important turning point for the show.


AVC: Do you ever think about what a “Hillary victory” version of this episode would have been like?

FB: Not as memorable. I think it would have been really funny, because Hillary is a funnier person. Trump is very one-note. There’s a lot of layers to why Hillary is funny. But it wouldn’t be our most listened-to episode, and we probably wouldn’t have seen that kind of a bump. Except that our lives would be a little bit easier.

Episode 75: Mr. Chapo Goes To Washington


AVC: Seventeen episodes later, you all went to Washington, D.C. for the Inauguration. 

BJ: Which is punishment enough. Matt has a tweet that said “Today is the stupidest day in American history, only to be outdone by every subsequent day in American history.” That was the inaugural. That was the feeling of the episode.

We were all in D.C. at our friend Libby Watson’s apartment. It was a packed house, literally everyone from the show: I was there, Matt, Amber, Virgil, Will, Felix, and Sam Kriss was our guest. It began with us watching the video of Richard Spencer getting punched, which was much needed.


WM: That [episode] was just our hangover from being in D.C. all week. We had been vexed by the city of D.C. all week long—we were there the single worst week to be in D.C. in human history.

MC: I think I like [this episode] more than everyone else. The thing about this whole Trump deal is that it is insane in a way that is so enormous that it can’t really be expressed. You can’t get it across, and so it ends up seeming like gesticulating and flailing. And that’s how you have half the country saying, “What’s the big deal?” Because you can’t express it! So the way that we had the raw anger of the election show, I feel like the reverse of the coin is that inauguration show, after we had months to absorb it, and then seeing it.

FB: It’s very middle school—you’re on a big trip with your friends, there’s barely any supervision, and you’re as immature as you can be. But it’s in the context of Donald Trump getting inaugurated.


People have told me that this episode really helped them out. Because this is awful, but it’s also fucking stupid. This is hilarious and horrifying at the same time. It spoke to people who already have lived in that reality of being under the gun.

Talking about D.C. and how much it sucked, it’s like, yeah, this is the swamp that Trump has come into and made more vicious, but it already sucked. It was already a terrible city full of terrible people, and just because Trump is going to be president, it doesn’t let anyone else off the hook.

WM: Adding to the flavor of the episode was actually being there, and sort of imbibing this whole atmosphere of D.C. The thing I was struck by walking around D.C. on that Thursday before the inauguration was the MAGA families sort of grazing up and down the mall—I was struck by how miserable they all looked. This was their big moment, their big party, and they all just looked sedated and sad, really.


MC: None of them were happy! That’s the thing. Their greatest dream had come true, and they just had a grim smugness at best. That was the most joy they could muster out of it.

The experience of seeing the Trump inauguration—it was surreal in a way that I can’t really convey. We tried, and I feel like we did a pretty good job. That’s why I like [this episode]. We’re all looking at this gristly, non-Euclidean monster, and we all have an individual perspective on it. It’s like the “Blind Man And The Elephant,” only it’s Cthulhu. And we’re all grabbing a tentacle and trying to describe it. We have not described it, but it’s a very valiant effort to do so.

That’s something people can relate to, that attempt to articulate just how strange things are, and how they’re so strange that you can’t convey it in a way that isn’t a cliché. You can’t convey it in a way that doesn’t just turn into banality, which is just so frustrating and terrifying, because this is the world. This is the horror of the world around you, and it has transcended naming. That episode is really just seven people in a room who saw Cthulhu and are trying to describe it to each other and failing—but trying.


BJ: There’s an interesting energy on this episode. It wasn’t a gloomy episode. We turned it into something entertaining. We were just walking around in a David Lynchian dream horror state. It was just unreal.

AVC: Was there talk about going to see it live, rather than watching on TV?

WM: There was absolutely no chance I was going to go to the Mall. This is a TV event. To fully commune with the moment, you have to watch it on TV. We would’ve missed so much being on the Mall.


MC: We watched the inauguration and we watched the speeches. The sensation was nausea and dread, but also a giddy sense of absolute possibility. Everything you thought were the constraints and norms surrounding the world around you were just thrown away. One of the reasons I love this episode very much is that I haven’t seen other media that has really even tried to grapple with that.

It’s amazing how people were like, [Claps hands.] “Okay, Trump’s president? All right, that’s the new thing. Let’s figure that out. What’ve we got, Cheeto jokes?” Everything’s going to get normalized at some point—it’s impossible not to; you have to live—but just take a second to really try to absorb it. Our episode is one of the few things that tried to do that.

AVC: Do you find it energizing, calibrating the show to this new and unexpected reality? 


BJ: I don’t want to pretend that it’s funny to us. This never should have happened, and I think we’d be having as much fun, if not more, if this hadn’t happened. It is exhausting to wake up in this world, and it’s scary—we don’t feel glad that we’re being proved right. I’m really proud when we’re able to do good shows. Recently we’ve done episodes on healthcare and the future of work. We are trying really hard to make something that is mostly funny, but that matters, and that, in a very small way, is able to carry people through this shit.

WM: It’s really modest goals that I’m trying to achieve here. I would like to see universal healthcare, the decommodification of a lot of things—housing and energy and education. I’d like a less violent police force. I’d like less war and foreign intervention. I don’t think these things are fringe positions by any means, and I think they can be achieved with democratic means. That being said, I’m pessimistic about the mechanism by which that representation is supposed to take place, in that we don’t really have an opposition party to give voice to these views, despite how broadly popular they are.

There’s a lot of anger, and a lot of it is justified anger, at our government, and at the elites. However, not all of that is good, as we’re seeing with the “alt-right” and youth-based reactionary movements. Anger in and of itself is not really good or bad, it’s just a fact that has to be dealt with. It can’t be wished away. If you’re going to engage politically with reality in this country, you are going to have to deal with anger. There’s a lot of rage out there.


FB: I’m like anyone else: I have a good idea of what we’re going to get going forward. We’re going to get the Republican Party’s general foreign policy vision, which is a combination of privatization and just cruel, cruel unaccountability for war crimes. The other half is stuff we don’t know, like another healthcare bill or tax breaks that are horrifying in ways we haven’t even conceived of. Or just some new psycho that Trump found on the internet that he’s going to give an important post to. But it’s also going to be things like Jeremy Corbyn.

And that’s the mix we’re going to get for the foreseeable future: a combination of known horrors, unknown horrors, and things we never accounted for, because we never thought we would get this future. And that can be really good sometimes. Breaking it down, we have about a quarter that isn’t horrifying. That’s a good ratio.