Panel one refers to Captain Kirk from Star Trek, and also references someone's assessment of Kirk from Star Trek 2, Wrath of Khan. It has also been argued that the pop culture image of Kirk (which was basically the template used in the 2009 Star Trek) puts too much emphasis on Kirk being with woman and being a rogue. It has been argued that, overall, he was actually pretty by-the-book during the series.
As someone who hasn't watched a lot of The Original Series (or, at least, can't remember it all that well), I'm taking absolutely everyone else's words for it to the point that I've basically decided there is a multiverse of Kirks (this does not count mirror universe Kirk).
As for The Simpsons, I've joked about figuring out The Simpsons timeline ever since Nintendo put out an official timeline for The Legend of Zelda. I consider a timeline for The Simpsons impossible and unnecessary, which might hint at what I think of the Zelda timeline.
It's fine if one enjoys that sort of thing, but I personally prefer Zelda games as standalone stories, and do not care at all about connecting them. Some direct sequels are nifty, but I feel like trying to connect EVERYTHING just makes a mess.
It was while writing this comic, however, that I first considered a Simpsons multiverse theory. I still consider it unnecessary, pointless, and potentially impossible, but I do think it could be interesting to try to divide episodes into separate continuities, and find timelines within those.
I mean, to a point. You'd probably want to limit how many seasons to include.
Science is optional when telling stories, though I do find it troubling when people take it beyond those stories and insist that actual dinosaurs didn't have feathers based entirely on them not looking as cool with feathers.