If I'm gonna drop some Fresh Hot Takes, I'm gonna go out on a limb and say that a) most pop cultural timelines are pure unadulterated cringe, and b) timelines that dip into offering insight into the pop culture of TTL are likewise almost always cringe, and it's because it's almost always Nothing But Hits.
Like, every film or TV show or video game is just pure uncut wish fulfillment. I mean AH is inherently indulgent in that it's historical fan fiction (and fan fiction is an inherently indulgent genre), but it'd be nice to read a TL where a Christopher Nolan makes a MGS movie starring Christian Bale and...it turns out to be Just Okay, maybe makes a bit of money, and society just moves on. I get the impulse to flesh out a world by dipping into pop culture, but it'd be nice if some of that was written with an eye towards plausibility and realism, or at the very least one where these fanwanky projects are made and don't succeed, or are compromised by the nature of the industry, or something.
Seriously, if I read one more TL where Alan Moore becomes the head writer of Doctor Who and the show goes on to be The Most Amazing Thing Ever, I'm just going to surgically blind myself so I won't have to roll my eyes anymore.