The crux of this order comes from the moment in Episode II where Anakin loses his hand. In the theater I remember being upset that there wasn't more of a moment for Anakin's loss of limb like there was for Luke. I couldn't believe they would drop the ball on one of the most connective moments between father and son. "Foul," I cried out, "George Lucas has lost his damn mind!"
And then it hit me: It doesn't matter if Anakin loses a hand. It only matters that Luke does because it explicitly shows him on the same path as his father.
So it got me thinking about how to watch these movies when they were all finished. Obviously if I watched Empire before Clones, I would want a big deal made of Anakin losing his hand. However, if I watched Clones (and by extension Sith) before Empire then the magical "I am your Father" moment and the lead up to it is lost. So I took a page out of the non-linear storytelling that Tarantino loves so much and came up with my order: 4, 1, 2, 5, 3, 6.
Let's break it down by movie, shall we?
Episode IV: A New Hope
This movie establishes that Obi-Wan and Anakin were friends in a more civilized age, fought in the clone wars, and ultimately that Anakin was killed by Darth Vader. It sets the stage for a lot of things that, if seen in numerical order, might not jive as well as it would as an introduction.
Episode I: The Phantom Menace
Operating as a flashback, Phantom shows us the world that Obi-Wan hinted at in A New Hope. Seen on it's own, or first, it might scare people off with it's wooden acting and confusing character choices, but with a bit of investment from a previous movie Menace becomes much more engaging to watch.
You know, for all the shit it gets, Menace isn't that bad. It's the only happy chapter of the saga and acts as a nice contrast to the rest of the movies. A contrast you'll see almost immediately with the next chapter.
Episode II: Attack of the Clones
Here's where things start getting fun and/or dark. Still in flashback mode, Clones illustrates the friendship and friction that Obi-Wan and Anakin had. You see the flares of that Skywalker impetuousness, the Skywalker compassion, the start of the Clone War, plenty of action, and a hint of despair.
It's here that you start to see the beginnings of The Empire, the tragedy of Anakin's path, and the threads start coming together.
Episode V: The Empire Strikes Back
Back to the "present", we find Luke on the next leg of his journey. Without the guiding hand of Obi-Wan, Luke is sent to train with Yoda who is more than reluctant to continue with him. Yoda thinks he's too old (which has been set up by him making the same argument about Anakin in Episode I and all the younglings in Episode II), too headstrong, and, probably, too whiny.
While Luke trains there are hints to his connection with Vader and explicit examples of him acting just like Anakin. So when Luke rushes in to save his friends because he just loves them so much (similar to Anakin in Episode II) and as a result gets his ass beat by a Sith Lord (again, just like Anakin), you expect that Vader is going to make another notch on his 'Skywalkers killed' belt. Then, right when you know that killing blow is going to happen, Vader drops the truth and shatters Luke's (and the audience's) world. Seething with questions of how such a thing could happen, it's time to turn to Episode III.
Episode III: Revenge of the Sith
With the idea of tragedy and betrayal lodged in our minds, we turn to Revenge of the Sith. Here we see Anakin and Obi-Wan fighting side by side in the Clone Wars, we watch a conflicted Anakin make terrible decisions while stumbling down his dark path, and ultimately Anakin's rise as Darth Vader.
Watching it this way, you feel Anakin's sadness as he's put into the suit, but not in a way that disturbs the reveal in Empire. Further, the birth of the twins isn't such a big deal because now you know their parentage (the Leia thing is admittedly still a bit wonky, but you can't win them all, right?)
Finally, with all the backstory in order we turn to the grand finale.
Episode VI: Return of the Jedi
The greatest thing about Jedi, to me, is Luke's ambiguity. From the beginning he's dressed like his father, freely choking people, and generally on the verge of headed to the dark side. All the way until the end and his big showdown with Vader in the presence of The Emperor you're not entirely sure what side Luke's going to come down on. In the end you realize that he represents equal parts of the light and the dark, he's the balance of the force. And, as foretold back in Episode I, Anakin 'returns' to bring that balance to the forefront by killing The Emperor and, at the same time, ensuring his own demise.
And there it is, the complete Saga virtually all plot twists intact and all the movies represented, perfect for the uninitiated viewer. Now if you could only find someone who's been living in a cave all their life so they'd be legitimately surprised by these overly spoiled twists....