When your entire comedy seems to be built around "Hah the stupid left thinks trans women are real women but they were born with penises", well, that's just not very funny to people who tend to have a non-homogenous friend group.
https://www.epsilontheory.com/gell-mann-amnesia/
I think Oliver is funny. His show makes good points and gives good arguments. It should not, however, by itself be the sole basis of one’s opinion on any given topic (not many things should) as many take it to be. It is intelligent and honest but also one-sided and biased.
They are, at least, not generally purposefully misleading in service of their bias, which is why I think people trust them more than a lot of other sources like cable news.
As someone who stopped taking certain news outlets on my side of the political spectrum serious after running into Gell-Mann once to often, I have to say, with decent backgroind in the topic we discuss here, aerospace and quality and such, this particular LWTN segment got it right. Heck, some of it was even than what I heard in my life from co-workers in the industry. I wouldn't go as far as doing a reverse Gell-Mann on LWTN based on this, but overall their reporting is, factually, correct. And they don't even try to hide their bias, nor donthey use to spin a story, which is refreshing if you ask me.
Another neat heuristic is that if there's a video/blog/whatever information product more often than once a week, it probably doesn't have enough research behind it to be reasonably accurate, even handed, and well, researched.
Journalism is stupidly expensive. Modern advertising actually doesn't pay enough to do it. Consider that just since 2008, newsroom employees have dropped by 20% or so, while the information space has significantly more manufactured misinformation than it ever used to. How many local government stories do you even see anymore? Are you paying for someone to keep tabs on your state legislators?
More often than not you won't find truth even if you read thousands of pages from a lawsuit.