On ChapoTrapHouse and Cumtown

To the second part, the answer is a little of column A and a little of column B.

The Chapo Guys have made it clear on several occasions that they see their podcast as entertainment first and politics second. That's not to say that they're not being authentic when they make political judgements but they're not under any delusions about their podcast being a kind of activism or a realpolitical force. Chapo really made it big as being the biggest and most successful exponents of anti-woke (in their own words, "dirtbag") leftism. This had always existed, of course, but was mostly a far left (i.e. outright communist) line, whereas the chapos made their name covering the 2016 democratic primaries as Bernie supporters. The anti-woke element is emphasised a lot, but to be frank, to my mind it's never amounted to more than a critique of the Democratic party establishment's willingness to clothe itself in the language of progressivism. For instance, the biggest controversy that they've been involved in a was a minor storm in a tea-cup over this tweet. Whilst the joke is pretty obviously a jab at liberal Hollywood's failure to properly deal with its own instances of abuse, it got interpreted in a fairly uncharitable light.. Iirc, the guy on the right, Josh Androsky, was a DSA chapter lead at the time and had to step down over the issue. It doesn't escape my notice that one of the main articles about this comes from Vox, which they've criticized alot.

Edit:(SSC readers may have read some Freddie DeBoer, he's on Scott's blogroll, their views are fairly in line with his.)

In theoretical terms, they're marxists who are broadly on board with the new wave of western social democratic politics. It's the Marxism that provides the theoretical underpinning of a lot of the anti-woke stuff, as they see a lot of liberal politics as a fairly shallow attempt to mask class interests. See here, "Bernie Bros", the attempt to brand Hilary Clinton as a feminist icon etc. They're particularly critical of the media classes complicity in the process. If you go a bit more into the weeds, they're also very critical of the New Left/60s moment in leftist politics, which they see as being a political failure that did a lot to cut the mainstream left from the working class, and providing the theoretical basis for identity politics post the 1980s.

The (liberal)left, as they see it, transformed itself from a broad based movement centered around the working class to one based essentially around what they call the "professional mangerial class", generally university educated knowledge-labourers who work either for the state or big corporate. Not only does this explain the left's turn away from New-Deal style policies, a regressive step politically, but it also explains the dominance of the right in terms of actual political achievements. As the party only represents a minority of the population, the PMC are basically using the two-party system to hold the remaining loyal white working class and minority groups "hostage". This is both morally wrong, and dangerous, as this often fails to drive turnout enough to be electorally successful. It's bad enough in the race for the presidency, but is even more dangerous in local politics where a committed base is needed to drive people out to vote. Obama's personal qualities and charisma, in this view, did a lot to mask the institutional failure and weakness of the democratic party. I'd go more into their critique of trumpism and the right more broadly if people are interested, but I'd give it its own post.

On the downside; in-jokes. A lot of them. It was a lot funnier back when they started off, but they've gotten a little stale. More broadly, . Especially as someone whose not American, they spend a lot of time dunking on Z-list op-eds and New York media-sphere journalists. If Chapo were the only news source in the world, you might be forgiven for thinking that Ross Douthat and David Brooks were read in every household.

With regards to Cumtown, it is, of course, explicitly a comedy podcast. The guys are seen as being Chapo adjacent to an extent, as they're left-progressive in terms of personal politics but make some fairly off-colour jokes . This is a fairly representative sample. Technically not racist, as it's joke about racial stereotypes, but it's riding the line enough that I wouldn't send it to anyone I knew in real life.

Cumtown, of course, is also notable for it's work on queering incestuous relationships.

Red Scare is a little more interesting theoretically. They have a broadly similar worldview to the Chapo Guys, but they're not afraid to be a little more culturally conservative. They were very critical of the me-too moment and feminism more broadly. Of course, they can get away with this because they're women. Camille Paglia is common point of reference for them, as is Christopher Lasch, the heterodox marxist who wrote The Culture of Narcissism. After her break-up with Adam Friedland, Dasha seems to be moving towards being a trad-cath, so we'll see how that turns out. If you've ever read The Last Psychiatrist (in fact, I think I heard Anna refer to him favourably on a couple of occasions), then you know the essence of what they have to say, although they frame their critique politically rather than personally.

TL:DR; They're only worth listening to if you enjoy it. Whilst there is a serious theoretical position behind what they talk about, and one i broadly agree with, it's behind tens or hundreds of hours of podcast content. If I was trying to convert someone politically opposed, I wouldn't send them to any of these podcasts.

The kind of person I would recommend Chapo to is a young person who's starting to become politically engaged. One could be forgiven for believing that the only two political postions available online are being a purple-haired woke-scold or a frog-poster, and the Chapo guys did a good job of staking out an online space for a third position (well, their subreddit eventually regressed to the former). For you, my distinguished intellectual friend, if you're interested in diving in more deeply, I can recommend some books or blog-posts.