There have traditionally been two main strategies for ordering the series. George Lucas would have us watch them in chronological order, which is obvious lunacy for numerous reasons (which Hilton studiously trots out), but most of us nerds have decided that the natural progression is actually in order of release (which is IV, V, VI, I, II, III). There are less flaws with that ordering. Hilton's reasoning here is a bit stilted, as it rests entirely on the "Special Edition" versions of Star Wars, but to my mind, the primary problem with the release order strategy is that the series then ends with a whimper. The prequels provide background and little else, and even that background is largely already known. Ending a six movie marathon with III would be quite a downer.
We could add a third strategy here for those bitterest of nerds, which is simply IV, V, VI without any acknowledgement that there were other Star Wars movies. Hilton, to his credit, acknowledges the charm of this option (and even links us to some Despecialized Editions of the movies), but he also sought out other orderings, just in case you actually do want to watch the other three movies. Enter the Ernest Rister sequence: IV, V, I, II, III, VI. The argument for this strategy is surprisingly compelling:
George Lucas believes that Star Wars is the story of Anakin Skywalker, but it is not. The prequels, which establish his character, are so poor at being character-driven that, if the series is about Anakin, the entire series is a failure. Anakin is not a relatable character, Luke is.Hilton goes on to then suggest his own variant of the Enest Rister sequence, which he calls the Machete Order: IV, V, II, III, VI. Haha, I see what he did there.
This alternative order (which a commenter has pointed out is called Ernst Rister order) inserts the prequel trilogy into the middle, allowing the series to end on the sensible ending point (the destruction of the Empire) while still beginning with Luke’s journey.
Effectively, this order keeps the story Luke's tale. Just when Luke is left with the burning question "how did my father become Darth Vader?" we take an extended flashback to explain exactly how. Once we understand how his father turned to the dark side, we go back to the main storyline and see how Luke is able to rescue him from it and salvage the good in him.
The prequel backstory comes at the perfect time, because Empire Strikes Back ends on a huge cliffhanger. Han is in carbonite, Vader is Luke’s father, and the Empire has hit the rebellion hard. Delaying the resolution of this cliffhanger makes it all the more satisfying when Return of the Jedi is watched.
Search your feelings, you know it to be true! Episode I doesn't matter at all. You can start the prequels with Episode II and miss absolutely nothing. The opening crawl of Episode II establishes everything you need to know about the prequels...Hilton has a very detailed and, naturally, nerdy description of why this is the superior sequence. For my part, I find this an acceptable order. My biggest concern is Vader's shocking revelation in Episode V. As long as that surprise is maintained, I'm pretty happy with the ordering, and there are a lot of things to like about the Rister or Machete ordering. Unfortunately, my nieces have already be indoctrinated (using the traditional order of release sequence), so I can't test the theory out on them, but if another opportunity to introduce someone to the series ever comes up, I might give it a shot. One nice thing about the Rister/Machete order is that both start with the best movies in the series, and once you get past the reveal in part V, you can lay out the strategies to the person watching and see which way they'd like to go.
Ok, so I think that's enough nerdiness for now. (Thanks to JVL for the link)