I just watched the Despecialized Edition for the first time tonight and it was an incredible and emotional experience. A film I haven’t seen in over 20 years.

During the viewing, I became overwhelmed with the desire to follow it immediately with Rogue One - which I think is an incredible film. It keeps me right in the sweet spot of the Empire/Rebellion conflict. The Empire is as basically as strong as it will ever get and the fragile Alliance scores a decisive blow. So for my own personal re-watching experience, I expect my order going forward to be:

ANH
Rogue One
ESB
ROTJ

I would not strongly advocate for this to be the viewing order for anyone completely new to the saga, but for a seasoned viewer it is a good experience. However, if you ever find yourself sharing the saga with someone who would really like to know how the Alliance got the plans that were the key plot device of A New Hope then this order could really work from a world-building perspective too.

Finally, I could be persuaded to start someone with Rogue One IF I knew the individual quite well and knew they would likely be turned off by the “dated” feel of a relatively low-budget 1977 movie. That being said, having not watched ANH through in at least a decade or more, I was both surprised and excited just how much the Despecialized Edition really, really holds up in 2018.