But then, as you correctly point out, some fields change in such a way that knowledge of their histories is nonessential for understanding their current state.
As to history proper, explaining the cold-war era proxy wars warrants a dive into WW2 and the onset of the cold war at some point; which then naturally leads you to dive into GD and WW1 as to why there was a WW2 in the first place; and why there was a WW1 to begin with; and why there was so much German-French animosity then; and why Europe was a powder keg at the time; etc. One can go on and on all the way back to the Roman Empire and Classical Greek history.
I'm admittedly an armchair historian at best, but methinks reversing the arrow of time in history books might yield a very interesting take on the topic that is a lot more approachable to kids and teenagers.
The original post, I think, was broadly about trying to engage people in the history of something they're not already interested in. For that, the device seems reasonable.
At least it does to me. But maybe that's because I actually did work backward from Led Zeppelin, to the Stones, to Muddy and Wolf, to Robert Johnson and learned to love them all. But if you started me on Johnson, or worse, Charlie Patton with those horrid recordings, you'd have lost me immediately.