For me it has to be the Berlin live episode and in top spot the live DnD episode, which I literally had to turn off after about 15 mins because it was too embarrassing. I can't imagine what being in the audience must have been like, lmao
(Obviously the true leftist answer is all of them)
I hate those cliquish episodes where they have some NY comedian or podcaster I never heard of and they're joking about people they known that I don't.
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notable exception: when the NY comedian is Stav
I'm really not a fan of the interview episodes in general, especially the cliquish ones though. I think the only slightly interesting ones are with people with, or who have had, actual power, and there's probably like, one or two good-ish interviews with an author. But I'm a very non-movie person and so any of those interviews, even with "celebrities", are incredibly boring. What inevitably happens is that they have to lib down their views, which isn't automatically bad (you don't wanna be confrontational all the time, life isn't a Twitter or Reddit thread) but it does really make me wonder what their true convictions are. But yeah, I skip all the interview episodes now. At least the movie episodes have some good riffs in them, even if the movies are terrible and I'll never watch them.
The other ones that really grate me are the doomer-y episodes; it really viscerally reminds me that I'm hearing about events through the perspective of relatively well-off New York podcasters and not really any coherent, broad, socialist viewpoint, regardless of what they actually individually believe. Matt is the least bad about this but even he suffers from it - and I think he'd be the first to admit that he has a big bias due to his current socioeconomic situation. I don't go to Chapo for leftist analysis, I'm perfectly aware it's an entertainment podcast, but hearing "Man, shit's terrible. This was another light-hearted episode, right guys? deflated laugh" for the hundredth time really grinds my gears.