I will take a look, but 35 minutes of John Oliver is a big ask.
Last time I watched him -- years ago -- he spent the entire segment in 100% outrage mode with a sledgehammer wall-of-sound style rhetoric in which nuance and empathy were entirely absent from his sequence of cherry-picked outrage nuggets.
But at the same time, I didn't find him very funny. Sam Kinison was also a loud outrage comic, but he was funny. But Kinison's yelling had an emotional honesty that Oliver lacked, since you can't really be too honest if you are doing politics on TV, especially partisan politics for the PMC class - a large amount of Oliver's material (that I saw) was basically mocking the beliefs of working class people. But perhaps he's changed. George Carlin was probably the one who made political comedy work the best, but he was deconstructing ideas that people have, and specifically ideas that you, the listener, had, often without questioning. That's what made people go "hmmm, that's interesting" when they listen to Carlin. Nobody says "Hmm, that's interesting" when listening to Oliver, they say "Boom! Nailed it! He's got their number!!" Subtlety, balance, making an honest effort to portray the complex world as it really is -- that was completely absent. It was all about caricaturing people or institutions as being unreasonable or suitable for mocking. Real life tends not to be like that.
I do wonder why people refer to Oliver as a news source or use him in arguments, it's basically the same thing as citing Rush Limbaugh. Limbaugh was actually much kinder -- sure, he also cherry picked examples to make his opponents look like fools, but he usually treated them as confused fools ("young minds, full of mush") rather than malicious actors. Limbaugh was also often self-deprecating and was able to change tone so that it wasn't all full throttle attack mode. But still I wouldn't cite one of his shows as evidence to support my point, as that's clearly a partisan show that is meant to be entertainment for those who agree with him rather than any kind of reasoned investigation.
I think the representativeness is the most important aspect to think about -- most likely the show focuses on and exaggerates absurdities / hypocrisies that are happening for a bigger punch, and as you point out, at the cost of its own credibility.
I know quite little on the subject we've been discussing - and I got more clarity reading what you wrote and thinking about it.
Stay awesome!
I feel like Last Week Tonight show about Museums was probably a decent overview of the state of things. I wonder, if you've seen it, you disagree with more than 10% of what's said?
https://www.youtube.com/watch?v=eJPLiT1kCSM