I'm generally a fan of Dimension 20 (D&D actual play show) but it does have a fair amount of woke cringe, mostly in the form of heavy handed "capitalism bad" and "organized religion bad" themes in certain seasons. Ally Beardsley, the resident enby on the main cast, is unsurprisingly the worst player and every PC she makes must reenact Ally's irl arc of escaping her evil Evangelical family and embracing queerness etc. Also just random annoying forced woke moments, e.g. in the talking animals mystery season "Of Mice and Murder", which is set in 1910s England, two random background NPCs are in a gay marriage that's not acknowledged as even noteworthy, there's just gay marriage in this setting. In "A Crown of Candy" (Candyland meets GoT), Ally's character Liam is an asexual teenage boy from the nobility, and an NPC tells him it's fine if he wants to marry someone of any gender. This in a low fantasy medieval setting where marriages among the nobility are political, arranged, and intended to produce heirs. It's just clearly done because of modern political reasons and they don't even have the balls to explore a fantasy culture with different values from modern coastie liberalism, even in settings like CoC where they theoretically are trying to do that. It's a setting based on medieval Europe with a powerful centralized monotheistic church, and not one of the PCs follows the mainstream religion, they're all agnostics or secret pagans. And of course, the church turns out to be the main antagonist. It just would have been such a more interesting season if even one of the players could stomach playing a fantasy Christian.
Another thing that gets called out as woke that I actually don't mind is casting non-whites in historical settings. I thought Joel Cohen's Macbeth was great. Macbeth is played by Denzel Washington and half the Scottish nobles are played by black actors, but I think it's a valid casting choice, Denzel fuckin killed it. They do it in The Great too, Count Orlo is British-Indian, Arkady is black, etc. and I don't care. I'm already suspending my disbelief that everyone is speaking modern English, I can pretty easily accept that these are non-white actors playing white Russians. Their races aren't brought up, nobody is saying "we wuz boyars", they're just having a diverse cast play theoretically white characters (and most of the cast is white btw) because that allows them to pick the best actors for the parts. I can't imagine another actor playing Orlo and I don't give a shit that he's one or two shades darker than his historical namesake.