Ehhhh about Entourage aging poorly. But I see what you mean.
I’ll give you Sex in the City. Never really was a fan but it always rubbed me the wrong way even in its original run.
In this era with how more cognizant we are of these things? Entourage aged very poorly.
The character of Ari Gold, who was a great performance and I love the character would not do well in this environment (on top of all the Jeremy Piven accusations). He's an abusive boss who reguarly uses homophobic, abusive, sexist, etc. language to berate people who are under him. With all that's happened with people talking about their sexists and otherwise mean bosses who majorly abused their power? Nah Ari isn't a good look. Even in the movie they had to tone him down.
The whole show just being "Rich People Problems" would get a fair amount if blow back. And how women are treated? All of them either ball busting "shrews" or just objects for the guys to gawk at or f***? I think I read somewhere that only 3-5 times in the whole series do women actually speak to each other in any meaningful way. Yeah it hasn't aged well at all.
I still love it. I used to rewatch it every summer and I still think season 2-5 are legit great TV. But looking at it now I can see the problems with it.
And even besides all that the premise is wore thin. They've said all they need to say with those characters and they're all almost 40 anyway.
Similar with Sex in the City. I've only seen part of the first movie and all of the 2nd movie, but it really is just the women version of Entourage (or Entourage is the male version of SitC) a bunch of rich people humping their way through the world (although I hear that they actually did some nice things with breast cancer awareness eventually). Ethnic people are a myth, all the gays are very campy. Neither aged well
A better move would've been/would be to bring back "How to Make it in America". That show was way ahead of it's time