We can also look at negative influences. Game of Thrones was a big deal...but it crashed and burned, HARD, which may sour a lot of people on the constantly grim-and-gritty realpolitik angle that some of Greyhawk leans into. Superhero media has taken a pretty steadily "grime it up" approach since at least The Dark Knight and possibly earlier, and multiple generations are kinda sick of having "heroes" in name only and "villains" who are often significantly more sympathetic (or, worse, a black-on-black morality where your choices are "serial sex offender and murderer" vs "heartless 'I did what I had to' underground rebel" and anyone who shows a lick of human decency rarely lives to regret that choice, e.g. The Boys.) Nuance is good--and we see that in things like Invincible--but so much of "nuance" has been either ham-fisted or bad-faith over the past two decades.
I strongly agree with this.
There is space for darker, grimmer stories, but while Game of Thrones had shock value in a lot of places, I've met more than a few people who have said they could never get into the series because, in their own words, they hated all the characters for being terrible people.
And I think this does move a little deeper at times. I would have a really, really hard time selling a grim setting to my groups. Maybe a little grey and smutty, but in the end, no one I know WANTS a realpolitik story... because the world sucks. Tap dancing around issues here, but a lot of people in younger generations just flat out don't have any hope for the future getting better, only worse. So, much like how in the 50's with the threat of nuclear war, culture pivoted to the white picket fence and eternally smiling family, a lot of modern culture looks for absurdity, wackiness, or just purely bright and wholesome things. Yes, yes, fight the monster, but save the world and don't become the monster in the process. Or find a way to save some monsters, even if not all of them.
I think Greyhawk can deliver that, I think it can deliver fun and whimsy and even silliness at times, but it does have to be careful since it would be so easy for it to fall down the other path, because people often mistake "Grim" for serious or well-done.