Don’t watch the prequels first. It’ll spoil the original trilogy. Machete or release order would be good.

Once you’re done 1-6, watch the others at your own will. Solo, Rogue One, the sequels, any order (but watch the sequels in order).

If you really get into all of the above, check out the Clone Wars animated show (watch it in chronological order), then Rebels. I would recommend watching the live action shows after the animated stuff because they continue a lot of those stories, but you could do it either way.

In my opinion, the best way to watch ALL of it is to watch it in release order. Nothing gets spoiled, and everything gets built upon what we already know.

If he really doesn't know about Vader's reveal in Empire, then you must watch the OT first, because the prequels will spoil one of the best plot twists in film history. Otherwise, watching the prequels first is fine.

But please do not watch the shitquels under any circumstances.

I'll jump in. What is the preferred order? I'm old. I saw the originals. I watched the prequels and nearly barfed. But now, there are all these side stories and Disney offshoots.

What order should I tackle them all in? A full rewatch, and in correct order. For the whole franchise?

If he really wants to watch Phantom Menace first, I suppose it would work if you jump from it to A New Hope.

If he is truly ignorant of Vader being Anakin, he’ll see a movie with kid Anakin, followed by a movie with old Obi-Wan lamenting how Vader killed Anakin at some point in the prequels, leaving the big reveal in place. Maybe actually making it better in some ways.

Honestly I don’t think Rogue One is worth watching. It’s pretty, but was very meddled with. I would highly recommend perhaps putting the Andor show in place instead of it. Either way, watching these after Episode 1 makes sense to me.

Then do the normal Machete Order.

If he doesn’t remember that the Han Solo movie exists, don’t remind him.

Of course that’s a BIG commitment. The sane way is to convince him just to watch the original trilogy first and the rest if he likes it.

Let him watch in 1-6 order. If he truly vibes with the prequels, he will have the intended Star Wars experience and might pick up on some ring theory clues.