Re: that first clip - the Brian Williams stuff absolutely shocking, but to me those opening jokes are about as funny (i.e. not very) as those from every other non-right wing American talk show. Am I wrang?
Reminds of when Fox tried a show in a vaguely The Day Today/Colbert Report/Jon Stewart Show style called the 1/2 Hour News Hour (similar joke title as John Oliver's godforsaken meme abyss) and it briefly became a liberal meme because it was apparently so bad and a huge embarassment. etc.
It was bad, true - but nearly identical in tone and content to a lot of the political humour on SNL at the same time and since. Just a shade right of the right of center not a shade left of the right of center. Extremely close to the Trump-era Hamberders phase of American liberal humour. Its entire premise is reducible to perceived fragility of the opposing party's voters. The same construction of gags towards fantasizing about winning arguments and scoring point rather than pointing ridiculous absurdities or just basic funny constructions in the writing. Stuff thats as far away from Conan O'brien as Little and Large were from Morcambe and Wise, stuff that has the form of something everyone agrees was popular because it was good, but the content is just packing peanuts.
What American liberal commentators miss with these shows is that its not laughs that drive them - its the smugness. Gutfeld has been very successful being very unfunny for a long time now. He's just smug, he knows he doesn't have to hit the mark. He can just scoff his way through bad material, toss out some edgelord barbs and 'highbrow' references to Mencius Moldbug, then go home and listen to his Amphetamine Reptile albums and laugh at Neil Hamburger clips on his phone. The fact that these shows tend to get cancelled swiftly doesn't really tell you anything about the popularity of the people involved or how successful they are as part of right wing branding and evangelising. The 1/2 Hour News Hour being apparently such a mortifying disaster never hurt anyone involved, and they got a fews clip of Rush Limbaugh being prez that got played over and over, and liberals still remember with rancor to this day. Gutfeld has got a bunch of people he hates fuming, that's all that matters. He'll gloat his way through until he has another try.